Sulfonamide derivatives of polycyclic dyes for analytical applications

• Main Authors: DREXHAGE, KARL-HEINZ, HAMERS-SCHNEIDER, MONIKA, ARDEN-JACOB, JUTTA, KEMNITZER, NORBERT UWE, ZILLES, ALEXANDER
• Format: Patent
• Language: English; French; German
• Published: 06.08.2014
• Subjects: ADHESIVES; CHEMISTRY; DYES; HETEROCYCLIC COMPOUNDS; INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIRCHEMICAL OR PHYSICAL PROPERTIES; LAKES; MEASURING; METALLURGY; MISCELLANEOUS APPLICATIONS OF MATERIALS; MISCELLANEOUS COMPOSITIONS; MORDANTS; NATURAL RESINS; ORGANIC CHEMISTRY; ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; PAINTS; PHYSICS; POLISHES; TESTING

1,2-Di- or 1,2,3,4-tetrahydroquinolin-4-yl-methanesulfonic acid derivatives (I) and analogous coumarin, xanthene, rhodol, carbopyronine, azine or amidopyrylium dyes (II) - (VII) are new. Di- or tetrahydroquinolinyl-methanesulfonic acid derivatives of formula (I) and polycyclic dyes of formulae (II) - (VII) are new. [Image] [Image] [Image] [Image] [Image] [Image] [Image] Dotted line : optional bond; R 1, R' : H or 1-20C hydrocarbyl (optionally containing heteroatom(s) and/or substituent(s)); R 2 - R 8, R : H, halo, OH, NH 2, SO 3H, COOH, CHO or 1-20C hydrocarbyl (optionally containing heteroatom(s) and/or substituent(s)); or R 1 + R 8 : group completing a ring system; or NRR' : ring system (optionally containing double bond(s)); X : OH, halo, OR 9, SR 1 0 or NR 1 1R 1 2; R 9 - R 1 2 : H or 1-20C hydrocarbyl (optionally containing heteroatom(s) and/or substituent(s), especially SO 3H, PO 3H 2 or COOH); R 1 3 : H or 1-20C hydrocarbyl (optionally containing heteroatom(s) and/or substituent(s)), especially H, aryl, carboxyphenyl, alkyl, perfluoroalkyl, cycloalkyl, pyridyl or carboxypyridyl); Y : O or S; or may also be Se in (III) or C(R) 2 in (VI); A -> : anion; provided that (III; Y = O; X = OH) and (IV; X = OH) are excluded. INDEPENDENT CLAIM are included for: (1) the preparation of polycyclic dyes (A) by sulfonating compounds having a terminal 4-methyl-dihydroquinoline group and optionally hydrogenating to the corresponding tetrahydroquinoline (provided that (A) do not include (III; Y = O; X = OH) or (IV; X = OH)); (2) the dyes (A) obtained by the process; and (3) the preparation of (I) - (VII).