Patent EP-0092520-A2 (EP)
Inventor: GREVE MANFRED
IPC: C09B44/02
Filed: 1983-04-13
Abstract: 1. Claims for the Contracting States : BE, CH, DE, FR, GB, IT, LI, NL, SE Basic and azo compounds, corresponding to one of the possible tautomeric forms of the formula (I)  see diagramm : EP0092520,P117,F1 wherein each R independently is hydrogen a (1-4C)-alkyl, (5-6C)-cycloalkyl or phenyl group, benzyl or phenylethyl, each T independently is hydrogen, i) -CN i1 )  see diagramm : EP0092520,P117,F2  i2 ) -COOR4 i3 ) -CONR5 R6 i4 ) -SO2 NR5 R6 i5 ) see diagramm : EP0092520,P117,F3  oder i6 )  see diagramm : EP0092520,P117,F4  r is 1 oder 2, each M independently is a group -R1 -NH-R0 , each M0 independently is a group R1 -NH-R0 , hydrogen, -NR11 R12 , (1-4C)-alkyl, hydroxy-(2-4C)- alkyl, (1-4C)-alkoxy-(1-4C)-alkyl, (5-6C)-cycloalkyl optionally substituted by 1 to 3 (1-4C)-alkyl groups, phenyl-(1-3C)-alkyl, phenyl-(1-3C)-alkyl, -V1 -NR13 R14 or -V2 -  see diagramm : EP0092520,P117,F5  A(cation) is an anion, S, when r stands for the number 2, is a) hydrogen, b) a group of formula  see diagramm : EP0092520,P118,F1  or c) -N=N-A-N=N-K, and F0 is a substituent conventionally used in azo chemistry, preferably F0 is halogen, NO2 , NH2 , alkyl, alkoxy, CN, trifluoroalkyl, phenyl, anilino, benzoyl, carbamoyl, phenoxy, halogenphenoxy, dihalogenphenoxy, alkylsulfonyl, phenylsulfonyl, alkylsulfonylamino, di-N-alkylaminosulfonyl or alkylsulfonyl, or S, when r stands for the number 1, is d) a group of the formula  see diagramm : EP0092520,P118,F2  wherein n is 0, 1 or 2, x is 0 or 1, each A independently is the residue of a tetrazo component, K is the residue of a diazo or coupling component, preferably free from sulfonic acid groups, of the pyrazolon-5, 5-aminopyrazole, aniline, phenol, acetoacetylalkyl- or arylamide, barbituric acid, dimedone, dimedonecarbonic acid ester or pyridone series e.g. the residue B, wherein r is 1 or 2, or 2,6-diaminopyridine, R1b , when x stands for 1, is a group of the formula e) -N=N-K1 , f) -N=N-A1 -N=N-K1 , g)  see diagramm : EP0092520,P118,F3  K1 has one of the significances of the group K or is an alpha- or beta-naphthol, an alpha- or beta-aminonaphthalene or an aminonaphthol, each R1 independently is an alkylene- or alkenylene group optionally interrupted by 1 or 2 heteroatoms or a phenylene- or cyclohexylene group, R0 is a group of the formula (Ia)  see diagramm : EP0092520,P118,F4  q is 0 or 1 and Rv is hydrogen, halogen, nitro, (1-4C)-alkyl or (1-4C)-alkoxy, R2 is a group of the formula h1 )  see diagramm : EP0092520,P119,F1  h3 )  see diagramm : EP0092520,P119,F2 or h2 )  see diagramm : EP0092520,P119,F3  -CO-(CH2 )1-3 -Z or hydrogen, wherein each D independently is the residue of a diazo compound, which may be substituted by substituents conventionally used in the azo chemistry, preferably a group  see diagramm : EP0092520,P119,F4  -A-N=N-K or  see diagramm : EP0092520,P119,F5 each R3 independently is hydrogen, (1-4C)-alkyl, -NR5 R6 or -CONR5 R6 , each R4 independently is (1-6C)-alkyl or phenyl-(1-3C)-alkyl, each R5 and R6 independently is hydrogen or (1-4C)-alkyl, each R7 independently is (1-4C)-alkyl, each R8 independently is hydrogen or (1-4C)-alkyl, each R9 independently is -S-, -O- or  see diagramm : EP0092520,P119,F6  each R10 independently is an (2-6C)-alkylene group or  see diagramm : EP0092520,P119,F7  where the atom marked * is bound to the -NR5 -, Q0 is an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group, wherein the N-atom is bound at the C-atom of the triazinyl group, Q is halogen, OH, -NH2 , (1-4C)-alkoxy, phenyl or Q0 , each Z independently is a group of formula -NR11 R12 or  see diagramm : EP0092520,P119,F8  each R11 and R12 independently is hydrogen, unsubstituted (1-6C)-alkyl, (2-6C) alkyl substituted by OH, CN or halogen, phenyl-(1-3C)-alkyl which may be substituted in the phenyl group by 1 to 3 substituents selected from chloro, (1-4C)-alkyl or (1-4C)-alkoxy, unsubstituted (5-6C)-cycloalkyl or (5-6C)-cycloalkyl substituted by 1 to 3 (1-4C)-alkyl groups, each R13 and R14 independently have one of the meanings of R11 and R12 , whereby one of the group R13 and R14 and preferably both groups are different from hydrogen, each R15 independently is a (1-4C)-alkyl group optionally substituted by phenyl, each V1 independently is (1-6C)-alkylene or (2-6C)-alkenylene, V2 independently is (2-6C)-alkylene or (2-6C)-alkenylene, the groups R5 and R4 , R11 and R12 , R13 and R14 respectively may form together with the N-atom, to which they are attached a saturated heterocyclic ring and R13 , R14 and R15 may form together with the N-atom, to which they are attached a pyridine ring or a saturated heterocyclic ring and the pyridine and the heterocyclic ring may be substituted by one, two or three (1-4C)-alkyl groups, R1a is hydrogen,  see diagramm : EP0092520,P120,F1  or  see diagramm : EP0092520,P120,F2  wherein whein x is the number 1, R1a is hydrogen, X1a is -NR5 -Q10 -NR11 R12 ,  see diagramm : EP0092520,P120,F3  -NR5 -COCH2 -NR11 R12 ,  see diagramm : EP0092520,P120,F4   see diagramm : EP0092520,P120,F5   see diagramm : EP0092520,P120,F6  or  see diagramm : EP0092520,P120,F7  m is 0 or 1, Q10 is  see diagramm : EP0092520,P120,F8  or linear or branched (2-6C)-alkylene, R2a is hydrogen or, when R1a is hydrogen and R1b stands for a group of formulae e) or f) is also OH, NH2 , (1-4C)-alkylcarbonylamino, benzoylamino or phenylamino, whose phenyl group may be substituted by 1 or 2 substituents selected from halogen, NO2 , NH2 , (1-4C)-alkyl and (1-4C)-alkoxy, each A1 independently is the residue of a tetrazo compound or the residue of a diazo- and/or coupling component and W0 is a divalent bridging group, mixtures of compounds of formula I, their acid addition salts of salts of acids and 1:1- or 1:2-metal complexes thereof, with the proviso that alpha) when the monoazo compounds b) of formula I are free from sulfonic acid groups, the compounds of formula b) have one and preferably two water solubilizing cationic groups or two water solubilizing protonatable basic groups or one cationic and one protonatable basic groups, and when the dis- and polyazo compounds of formula I are free from sulfonic acid groups, the dis- and polyazo compounds have at least two water-solubilizing cationic or at least two water-solubulizing protonatable basic groups or at least one cationic and at least one protonatable basic groups, and when the compounds of formula I contain sulfonic acid groups, the number of the cationic and/or protonatable basic groups is at least one greater than the sum of the sulfonic acid groups or possible additional anionic groups and beta) when r stands for the number 2, S is hydrogen and R0 is hydrogen, R1 is different from alkylene, T is different from CN and the group M is free from sulfonic acid groups. 1. Claims for the Contracting State : AT A process for preparing a basic compound or a basic azo compound corresponding to one of the possible tautomeric forms of the formula (I)  see diagramm : EP0092520,P141,F4  wherein each R independently is hydrogen, a (1-4C)-alkyl, (5-6C)-cycloalkyl-, or phenyl group ; benzyl or phenylethyl, each T independently is hydrogen, i) CN i1 )  see diagramm : EP0092520,P141,F5  i2 ) -COOR4 i3 ) -CONR5 R6 i4 ) -SO2 NR5 R6 i5 )  see diagramm : EP0092520,P142,F1  or i6 )  see diagramm : EP0092520,P142,F2  r is 1 oder 2, each M independently is a group -R1 -NH-R0 , each M0 independently is a group R1 -NH-R0 , hydrogen, -NR11 R12 , (1-4C)-alkyl, hydroxy(2-4C)-alkyl, (1-4C)-alkoxy-(1-4C)-alkyl, (5-6C)-cycloalkyl optionally substituted by 1 to 3 (1-4C)-alkyl radicals, phenyl(1-3C)-alkyl, -V1 -NR13 R14 or -V-  see diagramm : EP0092520,P142,F3  A(cation) is an anion, S, when r stands for the number 2, is a) hydrogen, b) a group of formula  see diagramm : EP0092520,P142,F4  or c) -N=N-A-N=N-K, and F0 is a substituent conventionally used in azo chemistry, preferably halogen, NO2 , NH2 , alkyl, alkoxy, CN, trifluoroalkyl, phenyl, anilino, benzoyl, carbamoyl, phenoxy, halogenphenoxy, dihalogenphenoxy, alkylsulfonyl, phenylsulfonyl, alkylsulfonylamino, di-N-alkylaminosulfonyl or alkylsulfonyl, or S, when r stands for the number 1, is d) a group of formula  see diagramm : EP0092520,P142,F5 wherein n is 0, 1 or 2, x is 0 or 1, each A independently is the residue of a tetrazo component, K is the residue of any diazo- or coupling component, preferably free from sulfonic acid groups, of the pyrazolone-5, 5-aminopyrazole, aniline, phenol, acetoacetylalkyl- or arylamide, barbituric acid, dimedone, dimedonecarbonic acidester, pyridone series, e.g. the group B, wherein r is 1 or 2, or 2,6-diaminopyridine, R1b , when x is 1, is a group of the formula e) -N=N-K1 , f) -N=N-A1 -N=N-K1 , g)  see diagramm : EP0092520,P142,F6 K1 has one of the significances of the group K or is an alpha- or beta-naphthol, an alpha- or beta-aminonaphthalene or an aminonaphthol, each R1 independently is an alkylene- or alkenylene group, which may be interrupted by 1 or 2 heteroatoms or a phenylene- or cyclohexylene group, R0 is a group of formula (Ia)  see diagramm : EP0092520,P143,F1  q is 0 or 1 and Rv is hydrogen, halogen, nitro, (1-4C)-alkyl or (1-4C)-alkoxy, R2 is a group of the formula h1 )  see diagramm : EP0092520,P143,F2  h3 )  see diagramm : EP0092520,P143,F3 or h2 )  see diagramm : EP0092520,P143,F4  -CO-(CH2 )1-3 -Z or hydrogen, wherein each D independently is the residue of a diazo compound, which may be substituted by substituents conventionally used in the azo chemistry, preferably a group of formula  see diagramm : EP0092520,P143,F5  -A-N=N-K or  see diagramm : EP0092520,P143,F6  each R3 independently is hydrogen, (1-4C)-alkyl, -NR5 R6 or -CONR5 R6 , each R4 independently is (1-6C)-alkyl or phenyl-(1-3C)-alkyl, each R5 and R6 independently is hydrogen or (1-4C)-alkyl, each R7 independently is (1-4C)-alkyl, each R8 independently is hydrogen or (1-4C)-alkyl, eac