Preparation of meso-substituted cyanine dye, for radiation-sensitive coating, e.g. for making printing plate, printed circuit boards or DVD, from 2-halo-cyclo-pentene or -hexene-dianil involves 1-stage introduction of end and meso-groups

Preparation of a meso-substituted cyanine dye of 2-(het)aryl-thio-, -seleno-, -oxy-, amino- or -sulfonyl-cyclopentene or -hexene type, 1,5(6)-di-substituted by quinolin-2- or -4-yl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl or indol-2-yl-ethenyl, comprises 1-stage reaction of 2-chloro- or 2-bromo-1,5(6)-dianil with (a) methylene or quaternary compound of end groups and (b) functionalized compound introducing 2-substituent. The process concerns preparation of a meso-substituted cyanine dye of formula (I) or (II), selected from 2-(het)aryl-thio-, -seleno-, -oxy-, amino- or -sulfonyl-cyclopentene or -hexene compounds 1,5(6)-di-substituted by quinolin-2- or -4-yl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl or indol-2-yl-ethenyl by a one-stage reaction in a water-miscible, inert organic solvent. It involves reacting a 2-chloro- or 2-bromo-1,5(6)-dianil (III) with (a) a methylene derivative (IV) or (V) or quaternary salt (VI) or (VII) and (b) a (hetero)aromatic functionalized compound (VIII), saturated 5- or 6-membered cyclic amine (IX) (optionally with another N, O or S atom in the ring) or 5- or 6-membered heteroaromatic compound (X), containing N atom(s) with a free electron pair, linked to the 2 adjacent ring C atoms by one single and one double bond: Ar-B (VIII) R1 = COOH, SO3H, H, halogen, NO2, CN, (substituted) 1-12 C alkyl or alkoxy or a condensed (hetero)aromatic ring system; R2 = (1-12 C alkandiyl)SO3H, (1-12 C alkandiyl)COOH or (substituted) 1-12 C alkyl or aryl; R2a = (1-12 C alkandiyl)SO3- or (1-12 C alkandiyl)COO- if n is 0, (substituted) 1-12 C alkyl or aryl if n is 1 or (1-12 C alkandiyl)-NR63+ if n is 2; R3, R4 = COOH, SO3H, COOR6, CN, NO2, OH, NR62, H, halogen, aryl or (substituted) 1-12 C alkyl or alkoxy; R5 = 1-12 C alkyl; R6 = H or (substituted) 1-12 C alkyl; Z- = a Cl, Br, I, SCN, PF6, SbF6, AsF6, aryl-SO3, -alkyl-O-SO3, PO4H2, CH3SO3, CF3SO3, (CH3SO2)2N, HSO4, BF4, ClO4 ions; Y = S-Ar, Se-Ar, O-Ar, NR6-Ar, SO2-Ar or -N-heterocycle; Ar = a (5-6-membered aromatic group, in which ring C atom(s) may be replaced by heteroatom(s) selected from N, O and S; L = 2-3 C alkandiyl, optionally mono- or poly-substituted by 1-10 C alkyl or alkoxy, aryl and/or halogen; A = Cl or Br; B = NHR6, SH, OH, SeH or SO2H Es wird ein einstufiges Verfahren zur Herstellung von meso-substituierten Cyanin-Farbstoffen bereitgestellt, welches die Umsetzung eines Farbstoffs (III) DOLLAR F1 mit (a) einer Methylenverbindung (IV) oder (V) oder einem qu