Patent GB-1388701-A (GB)
Title: Monoazo dyestuffs containing hydroxypyridone residues
IPC: D06P1/08
Filed: 1972-04-24
Abstract: 1388701 Monoazo dyes CASSELLA FARBWERKE MAINKUR AG 24 April 1972 [24 April 1971] 18838/72 Heading C4P New monoazo dyes of formula wherein R 1  is phenyl or naphthyl which may be mono- or disubstituted by alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogen or cyano; R 2  is -O-CO- or -CO-O-; R 3  is phenylene or naphthylene, which may be mono- or disubstituted by alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogen or cyano; X is hydrogen; cyano; carboxy; alkoxycarbonyl having 2 to 5 carbon atoms; pyridyl; thiazolyl; benzthiazolyl, imidazolyl; benzimidazolyl; thienyl, furyl; pyrrolyl; phenyl which may be substituted, cycloalkyl having 3 to 6 carbon atoms which may be substituted, benzyl which may be ring substituted the substituents in each case being alkyl having 1-4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogen or cyano; alkoxy having 1 to 6 carbon atoms; substituted or unsubstituted alkyl having 1 to 6 carbon atoms or substituted or unsubstituted alkenyl having 2 to 6 carbon atoms; the substituents in each case being hydroxy, cyano, alkanoyloxy having 2 to 5 carbon atoms, alkoxy having 1 to 4 carbon atoms, phenoxy, alkylaminocarbonyloxy having 2 to 5 carbon atoms, phenylaminocarbonyloxy, monoalkylamino or dialkylamino having 1 to 4 carbon atoms in each alkyl group or aziridinyl; Y is hydrogen; cyano; alkyl having 1 to 6 carbon atoms or alkenyl having 2 to 6 carbon atoms optionally substituted in each case by hydroxy, cyano, alkanoyloxy having 2 to 5 carbon atoms; alkoxy having 1 to 4 carbon atoms; phenoxy, alkylaminocarbonyloxy having 2 to 5 carbon atoms, phenylaminocarbonyloxy, monoalkylamino and dialkylamino having 1 to 4 carbon atoms in each alkyl group or aziridinyl; phenyl which may be substituted, cycloalkyl which may be substituted and having 3 to 6 carbon atoms or benzyl which may be ring substituted, each substituent being alkyl or alkoxy having 1 to 4 carbon atoms, halogen or cyano; -COOR 4 , -COR 5 , -SO 2 R 5  wherem R 4  is alkyl having 1 to 6 carbon atoms, R 5  is alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, benzyl, phenyl, substituted cycloalkyl having 3 to 6 carbon atoms in the ring, substituted phenyl or ring-substituted benzyl wherein each substituent is alkyl or alkoxy having 1 to 4 carbon atoms, halogen or cyano, or said alkyl substituted by hydroxy, cyano, alkanoyloxy having 2 to 5 carbon atoms; alkoxy having 1 to 4 carbon atoms, phenoxy, alkylaminocarbonyloxy having 2 to 5 carbon atoms, phenylaminocarbonyloxy, monoalkylamino and dialkylamino having 1 to 4 carbon atoms in each alkyl group or aziridinyl, and R 6  and R 7  are each hydrogen, alkyl having 1 to 6 carbon atoms, hydroxyalkyl having 1 to 6 carbon atoms, alkoxyalkyl having 1 to 4 carbon atoms in each alkyl moiety, cycloalkyl having 3 to 6 carbon atoms, benzyl or phenyl, or R 6  and R 7  together are -(-CH 2 -)- n  wherein n is 2 or 5, or together with the nitrogen atom to which they are attached represent morpholino or piperazino; and Z is hydrogen; amino; monoalkylamino having 1 to 4 carbon atoms; dialkylamino having 1 to 4 carbon atoms in each alkyl moiety; alkanoylamino having 2 to 5 carbon atoms; benzoylamino; alkyl having 1 to 6 carbon atoms or alkenyl having 2 to 6 carbon atoms optionally substituted in each case by hydroxy, cyano, alkanoyloxy having 2 to 5 carbon atoms, alkoxy having 1 to 4 carbon atoms, phenoxy, alkylamino-carbonyloxy having 2 to 5 carbon atoms, phenylaminocarbonyloxy, monoalkylamino and dialkylamino having 1 to 4 carbon atoms in each alkyl group or aziridinyl; phenyl which may be substituted, cycloalkyl which may be substituted and having 3 to 6 carbon atoms or benzyl which may be ring substituted, the substituents in each case being alkyl or alkoxy having 1 to 4 carbon atoms, halogen or cyano; pyridyl; thiazolyl; benzthiazolyl; imidazolyl; benzimidazolyl; thienyl, furyl or pyrrolyl, are described. The dyes wherein R 1  is phenyl, R 2  is -O-CO-, R 3  is phenylene which may be substituted by chlorine, bromine or cyano, X is methyl, Y is cyano and Z is alkyl having 1-4 carbon atoms, alkyl having 2-4 carbon atoms and substituted by hydroxy, by dimthylamino or by alkoxy of 1-4 carbon atoms, benzyl, phenyl, tolyl, 2- methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 2-hydroxy-phenyl, 3-hydroxyphenyl or 4-hydroxyphenyl, are disclaimed. The dyes are prepared by azo coupling and are used to colour synthetic fibres such as polyolefin, polyvinyl, polyamide, polacylamide, cellulose acetate and, in particular, polyester fibres in yellow to orange shades. Specification 1,302,221 is referred to.