Dimethine compounds of the coumarin series, a process for their preparation and their use as luminous dyestuffs
First Claim
1. A dimethine compound of the formula ##STR39## wherein A and B together with ##STR40## form a heterocyclic ring system selected from the group consisting of benzoxazole, benzimidazole, quinazolone, 1,3,4-oxadiazole and 1,3,4-thiadiazole rings, optionally benzo-fused and optionally substituted with up to two C1 -C4 -alkyl, CF3, C1 -C4 -alkoxy, halogen, C1 -C4 -alkoxycarbonyl, COOH, C1 -C4 -alkylsulphonyl, C5 -C6 -cycloalkyl, phenyl, phenyl-C1 -C3 alkyl, SO3 H, --(CH2)2 --O--, --(CH2)3 --, --(CH2)4 --, --OCH2 O--, --O--CH2 --CH2 --O-- and/or --C(CH3)2 --CH2 CH2 --C(CH3)2 -- radicals;
- R1 is C1 -C5 -alkyl, C3 -C4 -alkenyl, C5 -C6 -cycloalkyl, phenyl-C1-5 -alkyl, or phenyl,R2 is hydrogen, C1 -C5 -alkyl or phenyl-C1-5 -alkyl,R3 and R4 each independently is hydrogen or methyl, orR1 and R2 together can form a radical of the formula --(CH2)2 --Z--(CH2)2 --,R1 and R4 together can form a radical of the formula --(CH2)2 --, --(CH2)3 -- or --C(CH3)2 --CH2 --CH(CH3)-- and/orR2 and R3 together can form a radical of the formula --(CH2)3 --, andZ is A, CH2 or a direct bond, and wherein the cyclic and acyclic radicals can carry substituents which are customary in dyestuff chemistry.
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Accused Products
Abstract
Dimethine compounds of the coumarin series of the general formula ##STR1## with the substituent meanings given in the description are used for dyeing synthetic fibre materials, in particular those of polyester, polyamide, polyurethanes, polypropylene and polyacrylonitrile. Clear, luminous-red dyeings of high brilliancy are obtained. The dyestuffs can also be used as laser dyestuffs and as energy converters in light-collecting systems.
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Citations
10 Claims
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1. A dimethine compound of the formula ##STR39## wherein A and B together with ##STR40## form a heterocyclic ring system selected from the group consisting of benzoxazole, benzimidazole, quinazolone, 1,3,4-oxadiazole and 1,3,4-thiadiazole rings, optionally benzo-fused and optionally substituted with up to two C1 -C4 -alkyl, CF3, C1 -C4 -alkoxy, halogen, C1 -C4 -alkoxycarbonyl, COOH, C1 -C4 -alkylsulphonyl, C5 -C6 -cycloalkyl, phenyl, phenyl-C1 -C3 alkyl, SO3 H, --(CH2)2 --O--, --(CH2)3 --, --(CH2)4 --, --OCH2 O--, --O--CH2 --CH2 --O-- and/or --C(CH3)2 --CH2 CH2 --C(CH3)2 -- radicals;
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R1 is C1 -C5 -alkyl, C3 -C4 -alkenyl, C5 -C6 -cycloalkyl, phenyl-C1-5 -alkyl, or phenyl, R2 is hydrogen, C1 -C5 -alkyl or phenyl-C1-5 -alkyl, R3 and R4 each independently is hydrogen or methyl, or R1 and R2 together can form a radical of the formula --(CH2)2 --Z--(CH2)2 --, R1 and R4 together can form a radical of the formula --(CH2)2 --, --(CH2)3 -- or --C(CH3)2 --CH2 --CH(CH3)-- and/or R2 and R3 together can form a radical of the formula --(CH2)3 --, and Z is A, CH2 or a direct bond, and wherein the cyclic and acyclic radicals can carry substituents which are customary in dyestuff chemistry. - View Dependent Claims (2, 3, 4, 6, 8, 9, 10)
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5. Compound of the formula ##STR46##
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7. Process for the preparation of compounds of the formula (I), characterised in that salicylaldehydes of the formula ##STR49## wherein R1 -R4 have the meaning indicated above, are subjected to a condensation reaction with compounds of the formula ##STR50## wherein A and B have the meaning indicated above and E represents a carboxylic acid group, a carboxylic acid amide group or a nitrile group, with closure of the coumarin ring.
Specification
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- Resources
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Current AssigneeBayer AG
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Original AssigneeBayer AG
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InventorsHarnisch, Horst
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Primary Examiner(s)Demers, Arthur P.
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Application NumberUS06/296,661Time in Patent Office635 DaysField of Search542/430, 542/434, 542/436, 542/431, 542/437, 542/441, 260/343.44, 260/343.45, 252/301.17, 252/301.35, 252/301.34, 331/94.5 LUS Class Current252/301.17CPC Class CodesC09B 23/105 two >CH- groupsH01S 3/20 LiquidsH01S 3/213 including an organic dye
