Substituted diphenyl derivatives

A process for preparing diphenyl derivatives containing (i) at least one dialkyltriazenyl group and (ii) at least one sulfooxy group and/or at least one sulfamoyloxy group per molecule and their salts, solvates and solvates of these salts, wherein:

• aminophenyl derivatives of the formula
• where
• X is a direct C—C bond, CH2, CHOH, CO, S, SO, SO2, —N═N—, —CR7═CR8— or
• a divalent —C(O)—C*═CH—O— radical which together with the two adjacent carbon atoms of the ring a on which it is located forms a pyranone ring, with the ring b being located on the C* atom of this radical,
• R3, R6 are each, independently of one another, hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkyl-S—, C1-C4-alkyl-SO—, C1-C4-alkyl-SO2—, halogen, nitro, cyano or an —OSO2Y group,
• R4, R5 are each, independently of one another, an —NH2 group or an —OSO2Y group,
• R7 is hydrogen, methyl, ethyl or a phenyl radical which is substituted by the radicals R9, R10 and is bound directly to the R7-bearing carbon atom,
• R8 is hydrogen, ethyl, CN, NO2, —CH2CH2-halogen or CH2CH2OH,
• R9, R10 are each, independently of one another, hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, halogen, nitro, cyano, an —NH2 group or an —OSO2Y group,
• Y is OH or N(R1)2, and
• R1 is hydrogen, methyl or ethyl,
• with the proviso that, per total molecule (2), one or two NH2 groups and one or two —OSO2Y groups are located on any ring carbons of aromatic rings,
• are diazotized by means of a diazotizing agent in the presence of strong acid at low temperature in aqueous-acidic solution to form diazonium salts of the formula
• where
• X is a direct C—C bond, CH2, CHOH, CO, S, SO, SO2, —N═N—, —CR7═CR8— or
• a divalent —C(O)—C*═CH—O— radical which together with the two adjacent carbon atoms of the ring a on which it is located forms a pyranone ring, with the ring b being located on the C* atom of this radical,
• R3, R6 are each, independently of one another, hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkyl-S—, C1-C4-alkyl-SO_, C1-C4-alkyl-SO2—, halogen, nitro, cyano or an —OSO2Y group,
• R4, R5 are each, independently of one another, an —N2+AN− group or an —OSO2Y group,
• R7 is hydrogen, methyl, ethyl or a phenyl radical which is substituted by the radicals R9, R10 and is bound directly to the R7-bearing carbon atom,
• R8 is hydrogen, ethyl, CN, NO2, —CH2CH2-halogen or CH2CH2OH,
• R9, R10 are each, independently of one another, hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, halogen, nitro, cyano, an —N2+An− group or an —OSO2Y group,
• An− is a halogen anion or ½ sulfate (SO42−) anion,
• Y is OH or N(R1)2, and
• R1 is hydrogen, methyl or ethyl,
• with the proviso that, per total molecule (3), one or two diazonium groups and one or two —OSO2Y groups are located on any ring carbons of aromatic rings,
• and the diazonium salts (3) obtained are then reacted with dialkylamines of the formula
• HN(R2)2 (4)
• where R2 is methyl or ethyl,
• in the presence of acid binding agents,
• optionally followed by preparation of the salts from the compounds obtained and optionally followed by setting-free of the hydroxyl and/or acid groups from these salts.