Pyridone-methide azo dyestuffs with improved dyeing and printing properties for hydrophobic synethic fiber materials

A dyestuff of the formula ##STR208## or its tautomeric form wherein D is a radical selected from the group consisting of:

• ##STR209## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another represent H, T, F, Cl, Br, I, --CN, --NO.sub.2, --CH.dbd.O, --COT, --CO.sub.2 T.sup.1, --CONH.sub.2, --CONHT, CONT.sub.2, --CF.sub.3, --SO.sub.2 NH.sub.2, --SO.sub.2 NHT, --SO.sub.2 NT.sub.2, --SOT, --SO.sub.2 T, --SO.sub.3 T, --OT, --OH, --OCOT, --OCO.sub.2 T, --OSO.sub.2 T, --NH.sub.2, --NHT, --NT.sub.2, ##STR210## --NHCOH --NHCOT, --NHSO.sub.2 T and --COCO.sub.2 T, wherein R.sup.3 also represents --N.dbd.N--T.sup.4 or N.dbd.N--T.sup.5 and
• R.sup.6 also represents ST,
• A.sup.1 and A.sup.2 independently of one another denote H or a radical selected from the group consisting of T, --COH, --CO--T, --CO.sub.2 T, --CN, --CONH.sub.2, --CONHT, --CONT.sub.2, CF.sub.3,--NH.sub.2, --NHT, --NT.sub.2, --NH--COT, --NT--COT, --NHSO.sub.2 T, --NTSO.sub.2 T, --NO.sub.2, --NO, --SOT, --OH, --OT, --OCOT, --OCO.sub.2 T, --OSO.sub.2 T, Cl, Br and I
• A.sup.3 and A.sup.4 independently of one another represent --CN, --CO.sub.2 T, --CONH.sub.2, --CONHT, --CONT.sub.2, CF.sub.3, --CHO, --COT, --SO.sub.2 T, --SO.sub.3 T.sup.4, --SO.sub.3 T.sup.5, SO.sub.2 NH.sub.2, SO.sub.2 NHT, SO.sub.2 NT.sub.2, --SOT, --CH.dbd.NH, --CH.dbd.NT, --CT.dbd.NH, --CT.dbd.NT, ##STR211## --CO--CO.sub.2 T, --NO.sub.2, --NO, T.sup.4 or T.sup.5, or A.sup.3 and A.sup.4, together with the C atom to which they are bonded, represent a cyclic methylene-active compound of the formula (IIa) to (IIv), wherein the radicals are represented by ##STR212## and wherein the compound of the formula (IIa) to (IIv) is selected from the group consisting of ##STR213## wherein V.sup.1 represents H, Cl, Br, CH.sub.3, --CO.sub.2 T.sup.1, --CN, --NO.sub.2, --CF.sub.3 or --SO.sub.2 T.sup.1,
• A.sup.5 represents H or a radical of the formula T, --OT.sup.1, --NH.sub.2, --NHT, --NT.sub.2, --NHCOH, --NHCOT, --N.dbd.CH--T, --N.dbd.CT.sub.2 or NHSO.sub.2 T, wherein
• T represents T.sup.1 to T.sup.5
• T.sup.1 represents C.sub.1 -C.sub.20 -alkyl, C.sub.4 -C.sub.8 cycloalkyl or C.sub.6 -C.sub.10 -aryl-C.sub.1 -C.sub.8 -alkyl, each of which is unsubstituted or substituted by one or more substituents selected from the group consisting of ##STR214## --OCOH, COH, --OCOT, --OSO.sub.2 T, --O(CH.sub.2 C .sub.2 O).sub.1-6 COT, --OCO.sub.2 T, COT, --SO.sub.2 T, --CO.sub.2 T, --CN, --CONH.sub.2, --CONHT, --CONT.sub.2, --CO.sub.2 H, --SO.sub.2 NH.sub.2, --SO.sub.2 NHT, --SO.sub.2 NT.sub.2, --CF.sub.3, --NO.sub.2 and halogen,
• T.sup.2 and T.sup.3 represents C.sub.2 -C.sub.20 -alkenyl or C.sub.2 -C.sub.20 -alkinyl, each of which is unsubstituted or substituted by one or more substituents selected from the group of substituents as in T.sup.1
• T.sup.4 represents C.sub.6 -C.sub.16 -aryl which is unsubstituted or substituted by one or more substituents selected from the group consisting of ##STR215## --OCOH, COH, --OCOT, --OSO.sub.2 T, --O(CH.sub.2 CH.sub.2 O).sub.1-6 COT, --OCO.sub.2 T, COT, --SO.sub.2 T, --CO.sub.2 T, --CN, --CONH.sub.2, --CONHT, --CONT.sub.2, --CO.sub.2 H, --SO.sub.2 NH.sub.2, --SO.sub.2 NHT, --SO.sub.2 NT.sub.2, --CF.sub.3, --NO.sub.2 and halogen, --NH.sub.2, --NHT, --NT.sub.2, --NHCOH, --NHCOT, NHSO.sub.2 T, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkinyl, C.sub.1 -C.sub.10 -alkyl, C.sub.4 -C.sub.8 -cycloalkyl and C.sub.6 -C.sub.10 -aryl-C.sub.1 -C.sub.6 -alkyl;
• T.sup.5 represents thiophene, furan, pyrrole, 1,2-isothiazole, 1,3-thiazole, pyrrazole, oxazole, isooxazole, imidazole, triazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, benzothiazole, benzimidazole, benzoxazole, quinoline, isoquinoline, indole, coumarone, thionaphthene or tetrazole, each of which are unsubstituted or substituted one or more times by substituents selected from the group consisting of ##STR216## --OCOH, COH, --OCOT, --OSO.sub.2 T, --O(CH.sub.2 CH.sub.2 O).sub.1-6 COT, --OCO.sub.2 T, COT, --SO.sub.2 T, --CO.sub.2 T, --CN, --CONH.sub.2, --CONHT, --CONT.sub.2, --CO.sub.2 H, --SO.sub.2 NH.sub.2, --SO.sub.2 NHT, --SO.sub.2 NT.sub.2, --CF.sub.3, --NO.sub.2 and halogen, --NH.sub.2, --NHT, --NT.sub.2, --NHCOH, --NHCOT, NHSO.sub.2 T, C.sub.2 -C.sub.10 -alkenyl, C.sub.2 -C.sub.10 -alkinyl, C.sub.1 -C.sub.10 -alkyl, C.sub.4 -C.sub.8 -cycloalkyl and C.sub.6 -C.sub.10 -aryl-C.sub.1 -C.sub.6 -alkyl, or
• A.sup.1 and A.sup.2 together with the particular atoms in between, form an unsaturated unsubstituted or substituted 6-membered carbocylic radical,
• A.sup.2 and A.sup.3 independently of one another represent --CN, --CO.sub.2 T, --CONH.sub.2, --CONHT, --CONT.sub.2, CF.sub.3, --CHO, COT, --SO.sub.2 T, --SO.sub.3 T.sup.4, --SO.sub.3 T.sup.5, SO.sub.2 NH.sub.2, SO.sub.2 NHT, SO.sub.2 NT.sub.2, --SOT, --CH.dbd.NH, --CH.dbd.NT, --CT.dbd.NH, --CT.dbd.NT, --CO--COT, --NO.sub.2, --NO, T.sup.4 or T.sup.5- or
• A.sup.4 and A.sup.5 together with the atoms of the pyridone ring in between, form a fused ring of the formula ##STR217## wherein the N atom labelled with * corresponding to the pyridone nitrogen,
• X represents O, NH, NT, NCOT, NCO.sub.2 T or NSO.sub.2 T,
• K.sup.+ is --NH.sub.3.sup.+, --NHT.sub.2.sup.+, --NH.sub.2 T.sup.+, --NT.sub.3.sup.+ or a cycloimmonium ion,
• B.sup.- represent an organic or inorganic anion,
• Z represents --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --V wherein,
• V represents OH, OSO.sub.3 H, SSO.sub.3 H, OCOCH.sub.3, OPO.sub.3 H.sub.2, SCN, NHSO.sub.2 CH.sub.3, Cl, Br, F, OCOC.sub.6 H.sub.5, OSO.sub.2 --C.sub.6 H.sub.4, ›N(CH.sub.3).sub.3 !.sup.+ anion.sup.- or an unsubstituted or substituted pyridinium radical wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, COOH, SO.sub.3 H, CN and carboxamide or a heterocyclic fiber-reactive radical wherein said radical is 2,4-difluorotriazin-6-yl, 2,4-dichlorotriazin-6-yl and monohalogeno-sym-triazinyl radicals which are substituted by alkyl, aryl, amino, monoalkylamino, dialkylamino, aralkylamino, arylamino, morpholino, piperidino, pyrrolidino, piperazino, alkoxy, aryloxy, alkylthio or arylthio, where alkyl denotes optionally substituted C.sub.1 -C.sub.4 -alkyl, aralkyl denotes unsubstituted or substituted phenyl-C.sub.1 -C.sub.4 -alkyl and aryl denotes unsubstituted or substituted phenyl or naphthyl, and the substituents for alkyl are selected from the group consisting of halogen, hydroxyl, cyano, dialkylamino, morpholino, C.sub.1 -C.sub.4 -alkoxy, carboxyl, sulpho and sulphato;
• the substituents for phenyl and naphthyl are selected from the group consisting of sulpho, C.sub.1 -C.sub.4 - alkyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, halogen, acylamino, hydroxyl and amino or
• said heterocyclic fiber-reactive radicals are selected from the group consisting of 2-amino-4-fluorotriazin-6-yl, 2-methylamino-4-fluorotriazin-6-yl, 2-ethylamino-4-fluorotriazin-6-yl, 2-isopropylamino-4-fluoro-triazin-6-yl, 2-dimethylamino-4-fluorotriazin-6-yl, 2-diethylamino-4-fluorotriazin-6-yl, 2-.beta.-methoxy-ethylamino-4-fluoro-triazin-6-yl, 2-.beta.-hydroxyethylamino-4-fluoro-triazin-6-yl, 2-di-(.beta.-hydroxyethylamino)-4-fluoro-triazin-6-yl, 2-carboxymethylamino-4-fluoro-triazin-6-yl, 2-di-(carboxymethylamino)-4-fluoro-triazin-6-yl, 2-sulphomethyl-methylamino-4-fluoro-triazin-6-yl, 2-.beta.-cyanoethylamino-4-fluoro-triazin-6-yl, 2-benzylamino-4-fluoro-triazin-6yl, 2-.beta.-phenylethylamino-4-fluoro-triazin-6-yl, 2-benzyl -methylamino-4-fluoro-triazin-6-yl, 2-(4'-sulphobenzyl)-amino-4-fluoro-triazin-6-yl, 2-cyclohexylamino-4-fluoro-triazin-6-yl, 2-(o-, m- or p-methylphenyl)-amino-4-fluoro-triazin-6-yl, 2-(o-, m- or p-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(2,5'-disulphophenyl)-amino-4-fluoro triazin-6-yl, 2-o-, m- or p-chlorophenyl)-amino-4-fluoro-triazin-6-yl, 2-(o-, m- or p-methoxyphenyl)-amino-4-fluoro-triazin-6-yl, 2-(2'-methyl-4'-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(2'-methyl-5'-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(2'-chloro-4'-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(2'-chloro-5'-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(2'-methoxy-4'-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(o-, m- or p-carboxyphenyl)-amino-4-fluoro-triazin-6-yl, 2-(2',4'-disulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(3',5'-disulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(2'-carboxy4'-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(2'-carboxy-5'-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(6-sulpho-naphth-2'-yl)-amino-4-fluoro-triazin-6-yl, 2-(4',8'-disulphonaphth-2'-yl)-amino-4-fluoro-triazin-6-yl, 2-(6',8'-disulphonaphth-2'-yl)-amino-4-fluoro-triazin-6-yl, 2-(N-methyl-N-phenyl)-amino-4-fluoro-triazin-6-yl, 2-(N-ethyl-N-phenyl)-amino4-fluoro-triazin-6-yl, 2-(N-.beta.-hydroxyethyl-N-phenyl)-amino-4-fluoro-triazin-6-yl, 2-(N-isopropyl-N-phenyl)-amino-4-fluoro-triazin-6-yl, 2-morpho- lino-4-fluoro-triazin-6-yl, 2-piperidino-4-fluoro-triazin-6-yl, 2-(4',6',8'-trisulphonaphth-2'-yl)-amino-4-fluorotriazin-6-yl, 2-(3',6',8'-trisulphonaphth-2'-yl)-amino-4-fluoro-triazin-6-yl, 2-(3',6'-disulphonaphth-1'-yl)-amino-4-fluoro-triazin-6-yl, N-methyl-N-(2,4-dichlorotriazin-6-yl)-carbamyl, N-methyl-N-(2-methylamino-4-chlorotriazin-6-yl)-carbamyl, N-methyl-N-(2-dimethylamino-4-chlorotriazin-6-yl) carbamyl, N-methyl- or N-ethyl-N-(2,4-dichlorotriazin-6-yl)-aminoacetyl, 2-methoxy4-fluoro-triazin-6-yl, 2-ethoxy-4-fluoro-triazin-6-yl, 2-phenoxy-4-fluoro-triazin-6-yl, 2-(o-, m- or p-sulphophenoxy)-4-fluoro-triazin-6-yl, 2-(o-, m- or p-methyl- or -methoxy-phenoxy)-4-fluoro-triazin-6-yl, 2-.beta.-hydroxyethylmercapto-4-fluoro-triazin-6-yl, 2-phenylmercapto-4-fluoro-triazin-6-yl, 2-(4'-methylphenyl)-mercapto-4-fluorotriazin-6-yl, 2-(2',4'-dinitrophenyl)-mercapto-4-fluoro-triazin-6-yl, 2-methyl-4-fluoro-triazin-6-yl, 2-phenyl-4-fluoro-triazin-6-yl and the corresponding 4-chloro- and 4-bromotriazinyl radicals and the corresponding radicals obtainable by exchange of halogen with a tertiary base, selected from the group consisting of trimethylamine, triethylamine, dimethyl-.beta.-hydroxyethylamine, triethanolamine, N,N-dimethylhydrazine, pyridine, .alpha., .beta.- or .gamma.-picoline, nicotinic acid or isonicotinic acid, sulphinates, and di- or trihalogenopyrimidinyl radicals
• l represents 0 to 2,
• m represents 0 to 8 and
• n represents 0 to 6.