Process for the preparation of indigo derivatives and dyes for ceratinous fibers containing the same

• Main Authors: CHASSOT, LAURENT, ALLWOHN, JUERGEN, ROZZELL, DAVID
• Format: Patent
• Language: English; French; German
• Published: 21.05.2003
• Edition: 7
• Subjects: BEER; BIOCHEMISTRY; CHEMISTRY; COMPOSITIONS THEREOF; CULTURE MEDIA; DYEING LEATHER, FURS, OR SOLID MACROMOLECULAR SUBSTANCES INANY FORM; DYEING OR PRINTING TEXTILES; ENZYMOLOGY; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR; LAUNDERING; METALLURGY; MICROBIOLOGY; MICROORGANISMS OR ENZYMES; MUTATION OR GENETIC ENGINEERING; PROPAGATING, PRESERVING OR MAINTAINING MICROORGANISMS; SPIRITS; TEXTILES; TREATMENT OF TEXTILES OR THE LIKE; VINEGAR; WINE

Synthesis of indigo and 2,2'-bis(3-oxo-pyrrolo(2,3-b)pyridylidene) compounds (I) comprises (1) enzymatic conversion of a tryptophan derivative (II) with a tryptophanase enzyme in the presence of pyridoxal phosphate at 10-50 degrees C and then (2) enzymatic oxidation to (I) in the presence of NADH (hydrated form of beta -nicotinamide-adenine dinucleotide acting as cofactor) and a suitable oxidase enzyme at 10-50 degrees C. Synthesis of indigo and 2,2'-bis(3-oxo-pyrrolo(2,3-b)pyridylidene) compounds of formula (I) comprises: (1) enzymatic conversion of a tryptophan derivative of formula (II) with a tryptophanase enzyme in the presence of pyridoxal phosphate at 10-50 degrees C; and then (2) enzymatic oxidation to (I) in the presence of NADH (hydrated form of beta -nicotinamide-adenine dinucleotide acting as cofactor) and a suitable oxidase enzyme at 10-50 degrees C; X = nitrogen (N) or a methin group, CR4; R = hydrogen (H) or 1-4 carbon (C) alkyl; R1-4 = H, linear or branched 1-6 C alkyl, aryl, difluoromethyl, trifluoromethyl, halogen (fluorine (F), chlorine (Cl), bromine (Br) or iodine (I), amino, 1-6 C alkylamino, arylamino, hydroxyl, 1-4 C alkoxy, aryloxy, nitro, carboxy, carboxyalkyl, carboxamido, carboalkoxy, carboaryloxy or heterocyclyl; or R1R2 or R2R3 = methylenedioxy; R1-3 not = H in at least one case if X = CH. Independent claims are also included for multicomponent colorants for keratinous fibers.