Patent CA-1040193-A (CA)
Inventor: HEINRICH ERNST
IPC: C07D213/74
Filed: 1974-12-10
Granted: 1978-10-10
Abstract: Abstract of the Disclosure A water-insoluble azo dyestuff of the formula   wherein D is the residue of a benxene, napthalene, anthraquinone or heterocyclic diazo component which is free of ionic groups;        X is alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety, alkenyl or substituted alkenyl having 2 to 12 carbon atoms in the alkenyl moiety, cycloalkyl or substituted cycloalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety, phenalkyl or substituted phenalkyl having 1 to 2 carbon atoms in the alkyl moiety, phenyl, substituted phenyl, furyl, thienyl, thiazoyl, pyridyl, benzothiazolyl, inidazolyl, benzimidazolyl, pyrrolyl or hydrogen;        Y is cyanno, alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety, alkenyl or substituted alkenyl having 2 to 12 carbon atoms in the alkenyl moiety, cycloalkyl or substituted cycloalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety, phenalkyl or substituted phenalkyl having 1 to 2 carbon atoms in the alkyl moiety, phenyl, substituted phenyl,  -COOR1, -COR2,  , -8O2R2,   or hydrogen with the proviso that only one of X and Y is simultaneously hydrogen;     Z1 is  ,  , -NH-OR10 or   and Z2 is -O-(CnH2nO)m-R12 or -S-(CH2H2nO)m-R12 wherein R1 and R2 are alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety, alkenyl or substituted alkenyl having 2 to 12 carbon atoms in the alkenyl moiety, cycloalkyl or substituted cycloalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety, phenalkyl or substituted phenylalkyl having 1 to 2 carbon atoms in the alkyl moiety, phenyl, substituted phenyl, piperazino, furyl, thienyl, pyridyl, thiazoyl, benzothiazoyl, imidazoyl, benzimidazoyl or pyrrolyl;         R3 and R4 taken separately, are hydrogen, alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety, cycloalkyl or substituted cycloalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety, phenalkyl or substituted phenalkyl having 1 to 2 carbon atoms in the alkyl moiety or phenyl or substituted phenyl and R3 and R4, taken together, are alkylene having 2 to 5 carbon atoms or said alkylene interrupted by oxygen, sulfur or nitrogen;           R5 and R6, taken separately, are hydrogen, alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety, alkenyl or substituted alkenyl having 2 to 12 carbon atoms in the alkenyl moiety, cycloalkyl or substituted cyclo-alkyl having 3 to 8 carbon atoms in the cycloalkyl moiety, phenalkyl or substituted phenalkyl having 1 to 2 carbon atoms in the alkyl moiety and R5 and R6, taken together, are alkylene having 2 to 5 carbon atoms or said alkylene interrupted by oxygen, sulfur or nitrogen;             R7 is hydrogen, alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety, phenyl or substituted phenyl, R8 and R9 are alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety, phenyl or substituted phenyl;           R10, taken separately, is hydrogen, alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety or phenalkyl or substituted phenalkyl having 1 to 2 carbon atoms in the alkyl moiety;           R11, taken separately, is alkyl substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety;           R10 and R11, taken together, are alkylene having 2 to 5 carbon atoms;           R12 is hydrogen, alkyl or substituted alkyl having 1 to 12 carbon atoms in the alkyl moiety, alkenyl or substituted alkenyl having 2 to 12 carbon atoms in the alkenyl moiety, cycloalkyl or substituted cycloalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety, phenalkyl or substituted phenalkyl having 1 to 2 carbon atoms in the alkyl moiety, phenyl or substituted phenyl; n is 2, 3 or 4; m is 0, 1 or 2; there being up to two substituents for each of said substituted alkyl and substituted alkenyl, each said substituent being selected from the group consisting of cyano, hydroxy, acetoxy, alkoxy having 1 to 2 carbon atoms, phenoxy, alkylamino-carboxyloxy having 2 to 3 carbon atoms, phenylaminocarboxyloxy, monoalkylamino and dialkylamino having 1 to 2 carbon atoms in each alkyl moiety,   wherein Z is alkylene containing 2 to 5 carbon atoms or said alkylene interrupted by oxygen, sulfur or nitrogen and   wherein R13 is alkyl having 1 to 2 carbon atoms and R14 is acetyl or benzoyl:           there being up to two substituents for each of said substituted cycloalkyl, substituted phenalkyl and substituted phenyl, each of said substituents being selected from the group consisting of bromine, chlorine, cyano, alkyl having 1 to 3 carbon atoms and alkoxy having 1 to 2 carbon atoms and the total number of carbon atoms in X, Y, Z and Z2 being not more than 24;           process of producing said dyestuffs and use of said dyestuffs for dyeing and printing hydrophobic materials.