Patent TW-427976-B (TW)
Title: Pyridone-methide azo dyestuffs, process for their preparation, their use and their novel intermediates
Inventor: HAMPRECHT RAINER
IPC: C09B29/36
Filed: 1996-09-19
Granted: 2001-04-01
Abstract: A dyestuff of the formula (I), or its tautomeric form, wherein D is a radical selected from the group consisting of: formulas, wherein R1, R2, R3, R4, R5 and R6 independently of one another denotes H, T, F, CI, Br, I, -CN, -NO2, -CH=O, -COT, -CO2T1, -CONH2, -CONHT, CONT2, -CF3, -SO2NH2, -SO2NHT, -SO2NT2, -SOT, -SO2T, -SO3T, -OT, -OH, -OCOT, -OCO2T, -OSO2T, -NH2, -NHT, -NT2, -NHCOH, -NHCOT, -NHSO2T or -COCO2T, wherein R3 can additionally denote -N=N-T4 or -N=N-T5 and R6 can additionally denote ST, A1 and A2 independently of one another denote H or a radical selected from the group consisting of T, -COH, -CO-T, -CO2T, -CN, -CONH2, -CONHT, -CONT2, CF3, -NH2, -NHT, -NT2, -NH-COT, -NT-COT, -NHSO2T, -NTSO2T, -NO2, -NO, -SO2T, -OH, -OT, -OCOT, -OCO2T, -OSO2T, CI, Br and I, A3 and A4 independently of one another represent -CN, -CO2T, -CONH2, -CONHT, -CONT2, CF3, -CHO, -COT, -SO2T, -SO3T4, -SO3T5, SO2NH2, SO2NHT, SO2NT2, -SOT, -CH=NH, -CH=NT, -CH=NH, -CT=NT, -CO-CO2T, -NO2, -NO, T4 or T5, or A3 and A4, together with the C atom to which they are bonded, represent a cyclic methylene-active compound of the formula (IIa) to (IIv), where these radicals are shown in the form of formula (II), and wherein the compound of the formula (IIa) to (IIv) is selected from the group consisting of formulas, wherein V1 represents H, CI, Br, CH3, -CO2T1, -CN, -NO2, -CF3 or -SO2T1, A5 represents H or a radical of the formula T, -OT1, -NH2, -NHT, -NT2, -NHCOH, -NHCOT, -N=CH-T, -N=CT2 or NHSO2T, wherein T represents T1 to T5, T1 represents C1-C20-alkyl, C4-C8-cycloalkyl or C6-C10-aryl-C1-C8-alkyl, each of which is unsubstituted or substituted by one or more substituents selected from the group consisting of -OCOH, COH, -OCOT, -OSO2T, -O(CH2CH2O)1-6COT, -OCO2T, COT, -SO2T, -CO2T, -CN, -CONH2, -CONHT, -CONT2, -CO2H, -SO2NH2, -SO2NHT, -SO2NT2, -CF3, -NO2 and halogen, T2 and T3 independently of one another represent C2-C20-alkenyl or C2-C20-alkinyl, each of which is unsubstituted or substituted by one or more substituents from the group of substituents as in T1, T4 represents C6-C16-aryl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of -OCOH, COH, -OCOT, -OSO2T, -O(CH2CH2O)1-6COT, -OCO2T, COT, -SO2T, -CO2T, -CN, -CONH2, -CONHT, -CONT2, -CO2H, -SO2NH2, -SO2NHT, -SO2NT2, -CF3, -NO2 and halogen, -NH2, -NHT, -NT2, -NHCOH, -NHCOT, NHSO2T, C2-C10-alkenyl, C2-C10-alkinyl, C1-C10-alkyl, C4-C8-cycloalkyl and C6-C10-aryl-C1-C6-alkyl; T5 denotes 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 optionally substituted one or more times by substituents selected from the group consisting of -OCOH, COH, -OCOT, -OSO2T, -O(CH2CH2O)1-6COT, -OCO2T, COT, -SO2T, -CO2T, -CN, -CONH2, -CONHT, -CONT2, -CO2H, -SO2NH2, -SO2NHT, -SO2NT2, -CF3, -NO2 and halogen, -NH2, -NHT, -NT2, -NHCOH, -NHCOT, NHSO2T, C2-C10-alkenyl, C2-C10-alkinyl, C1-C10-alkyl, C4-C8-cycloalkyl and C6-C10-aryl-C1-C6-alkyl; or A1 and A2 and/or A2 and A3 together with the particular atoms in between, form an unsaturated, optionally substituted 6-membered carbocyclic radical, and/or A4 and A5 together with the atoms of the pyridone ring in between, form a fused ring of the formula, wherein the N atom labelled with corresponds to the pyridone nitrogen, X represents O, NH, NT, NCOT, NCO2T or NSO2T, K⊕ is -NH3⊕, -NHT2⊕, -NH2T⊕, -NT3⊕ or a cycloimmonium ion, B⊖ is an organic or inorganic anion, Z represents -CH=CH2 or -CH2CH2-V, wherein V represents OH, OSO3H, SSO3H, OCOCH3, OPO3H2, SCN, NHSO2CH3, CI, Br, F, OCOC6H5, OSO2-C6H4, [N(CH3)3]⊕ anion⊖ or an optionally substituted pyridinium radical wherein the substituents are selected from the group consisting of C1-C4-alkyl, COOH, SO3H, CN and carboxamide; or a heterocyclic fibre-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 C1-C4-alkyl, aralkyl denotes optionally substituted phenyl-C1-C4-alkyl and aryl denotes optionally substituted phenyl or naphthyl, and the substituents for alkyl are selected from the group consisting of halogen, hydroxyl, cyano, dialkylamino, morpholino, C1-C4-alkoxy, carboxyl, sulpho and sulphato; and the substituents for phenyl and naphthyl are selected from the group consisting of sulpho, C1-C4-alkyl, C1-C4-alkoxy, carboxyl, halogen, acylamino, hydroxyl and amino, said heterocyclic fiber-reactive radicals are selected from the group consisting of 2-amino-4-fluoro-triazin-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-β-methoxy-ethylamino-4-fluoro-triazin-6-yl, 2-β-hydroxyethylamino-4-fluoro-triazin-6-yl, 2-di-(β-hydroxyethylamino)-4-fluoro-triazin-6-yl, 2-carboxymethylamino-4-fluoro-triazin-6-yl, 2-di(carboxymethyl-amino)-4-fluoro-triazin-6-yl, 2-sulphomethyl-methylamino-4-fluoro-triazin-6-yl, 2-β-cyanoethylamino-4-fluoro-triazin-6-yl, 2-benzylamino-4-fluoro-triazin-6yl, 2-β-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'-sulpho-phenyl)-amino-4-fluoro-triazin-6-yl, 2-(2'-methoxy-4'-sulphophenyl)-amino-4-fluoro-triazin-6-yl, 2-(o-, m- or p-carboxphenyl)-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'-carboxy-4'-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)-amino-4-fluoro-triazin-6-yl, 2-(N-β-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-fluoro-triazin-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-methoxy-4-fluoro-triazin-6-yl, 2-ethoxy-4-fluoro-triazin-6-yl, 2-phenoxy-4-fluoro-triazin-6-yl, 2-(o-, m- or p-sulpho-phenoxy)-4-fluoro-triazin-6-yl, 2-(o-, m- or p-methyl- or -methoxy-phenoxy)-4-fluoro-triazin-6-yl, 2-β-hydroxyethylmercapto-4-fluoro-triazin-6-yl, 2-phenyl-mercapto-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- bromo-triazinyl radicals and the corresponding radicals obtainable by exchange of halogen with tertiary bases selected from the group consisting of trimethylamine, triethylamine, dimethyl-β-hydroxyethylamine, triethanolamine, N, N-dimethylhydrazine, pyridine, Α, β- or γ -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.