Patent US4384973A successfully refreshed from Google Patents.
US4384973A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Dimethine compounds of the coumarin series, a process for their preparation and their use as luminous dyestuffs
Assignee: Bayer AG
•
Filing: 1981-08-27
•
Granted: 1983-05-24
•
Expires: 2001-08-27
Abstract
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.
Inventors
- 👤 Horst Harnisch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 15:46
CPC Classifications
C; C09; C09B; C09B23/00; C09B23/10; C09B23/105; H; H01; H01S; H01S3/00; H01S3/14; H01S3/20; H01S3/213
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
266 words
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 C 1 -C 4 -alkyl, CF 3 , C 1 -C 4 -alkoxy, halogen, C 1 -C 4 -alkoxycarbonyl, COOH, C 1 -C 4 -alkylsulphonyl, C 5 -C 6 -cycloalkyl, phenyl, phenyl-C 1 -C 3 alkyl, SO 3 H, --(CH 2 ) 2 --O--, --(CH 2 ) 3 --, --(CH 2 ) 4 --, --OCH 2 O--, --O--CH 2 --CH 2 --O-- and/or --C(CH 3 ) 2 --CH 2 CH 2 --C(CH 3 ) 2 -- radicals; R 1 is C 1 -C 5 -alkyl, C 3 -C 4 -alkenyl, C 5 -C 6 -cycloalkyl, phenyl-C 1-5 -alkyl, or phenyl, R 2 is hydrogen, C 1 -C 5 -alkyl or phenyl-C 1-5 -alkyl, R 3 and R 4 each independently is hydrogen or methyl, or R 1 and R 2 together can form a radical of the formula --(CH 2 ) 2 --Z--(CH 2 ) 2 --, R 1 and R 4 together can form a radical of the formula --(CH 2 ) 2 --, --(CH 2 ) 3 -- or --C(CH 3 ) 2 --CH 2 --CH(CH 3 )-- and/or R 2 and R 3 together can form a radical of the formula --(CH 2 ) 3 --, and Z is A, CH 2 or a direct bond, and wherein the cyclic and acyclic radicals can carry substituents which are customary in dyestuff chemistry.
Claim 2
Dependent Claim
266 words
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 C 1 -C 4 -alkyl, CF 3 , C 1 -C 4 -alkoxy, halogen, C 1 -C 4 -alkoxycarbonyl, COOH, C 1 -C 4 -alkylsulphonyl, C 5 -C 6 -cycloalkyl, phenyl, phenyl-C 1 -C 3 alkyl, SO 3 H, --(CH 2 ) 2 --O--, --(CH 2 ) 3 --, --(CH 2 ) 4 --, --OCH 2 O--, --O--CH 2 --CH 2 --O-- and/or --C(CH 3 ) 2 --CH 2 CH 2 --C(CH 3 ) 2 -- radicals; R 1 is C 1 -C 5 -alkyl, C 3 -C 4 -alkenyl, C 5 -C 6 -cycloalkyl, phenyl-C 1-5 -alkyl, or phenyl, R 2 is hydrogen, C 1 -C 5 -alkyl or phenyl-C 1-5 -alkyl, R 3 and R 4 each independently is hydrogen or methyl, or R 1 and R 2 together can form a radical of the formula --(CH 2 ) 2 --Z--(CH 2 ) 2 --, R 1 and R 4 together can form a radical of the formula --(CH 2 ) 2 --, --(CH 2 ) 3 -- or --C(CH 3 ) 2 --CH 2 --CH(CH 3 )-- and/or R 2 and R 3 together can form a radical of the formula --(CH 2 ) 3 --, and Z is A, CH 2 or a direct bond, and wherein the cyclic and acyclic radicals can carry substituents which are customary in dyestuff chemistry.
Claim 3
Dependent Claim
157 words
Dimethine compounds according to claim 1, of the formula ##STR41## wherein Z 1 and Z 2 each by itself represents a C 1 -C 4 -alkyl radical which is substituted by Cl or CN, or phenyl-C 1 -C 3 -alkyl, Z 3 and R 4 independently of one another represent hydrogen, D represents a radical of the formula ##STR42## X represents O, S, NH, N-C 1 -C 4 -alkyl, N-benzyl N-phenyl ##STR43## or, V represents O or S, Y 1 represents hydrogen, C 1 -C 4 -alkyl, chlorine, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkyl-sulphonyl, phenyl or cyclohexyl, Y 2 represents hydrogen, methyl or chlorine and Y 3 represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 2 -alkoxy or chlorine, and wherein Z 1 and Z 4 , and Z 2 and Z 3 together can represent a radical of the formula --(CH 2 ) 3 --.
Claim 4
Dependent Claim
61 words
Dimethine compounds according to claim 1, of the formula ##STR44## wherein T 1 and T 2 each by itself represents C 1 -C 4 -alkyl or phenyl-C 1 -C 3 -alkyl, Q represents a radical of the formula ##STR45## W represents O, S, NH or NH-CO (CO on the aromatic ring) and T 3 represents hydrogen, methyl, methoxy, ethoxy or chlorine.
Claim 5
Dependent Claim
10 words
Dimethine compounds according to claim 3, characterised in that W=0.
Claim 6
Dependent Claim
5 words
Compound of the formula ##STR46##
Claim 7
Dependent Claim
5 words
Compound of the formula ##STR46##
Claim 8
Dependent Claim
63 words
Process for the preparation of the dimethine compounds according to claim 1, characterised in that aldehydes of the formula ##STR47## wherein R 1 , R 2 , R 3 and R 4 have the meaning given, or functional derivatives of these aldehydes, are subjected to a condensation reaction with cyanomethyl compounds of the formula ##STR48## wherein A and B have the meaning given.
Claim 9
Dependent Claim
71 words
Process for the preparation of compounds of the formula (I), characterised in that salicylaldehydes of the formula ##STR49## wherein R 1 -R 4 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.
Claim 10
Dependent Claim
71 words
Process for the preparation of compounds of the formula (I), characterised in that salicylaldehydes of the formula ##STR49## wherein R 1 -R 4 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.
Claim 11
Dependent Claim
112 words
Mixtures or combinations of dimethine compounds according to claim 1 with 7-di-(C 1 -C 4 -alkyl)-amino-3-heteryl-coumarin dyestuffs, in which heteryl represents a benzoxazole, benzothiazole, benzimidazole, quinazolone or 5-phenyl-1,3,4-thiadiazole radical which is optionally substituted by 1 or 2 C 1 -C 4 -alkyl radicals, 1 or 2 chlorine atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl, cyclohexyl or phenyl, or with 10-(C 1 -C 2 -alkoxy)-benzo[k,1]xanthene-3,4-dicarboxylic acid imides, characterised in that these mixtures or combinations correspond, on polyester, to a luminous orange colour shade in accordance with the Standard RAL 2005 laid down by the German Standards Sub-Committee for Terms of Delivery and Quality Assurance.
Claim 12
Dependent Claim
15 words
A luminous dyestuff composition comprising a dimethine compound according to claim 1, plus a carrier.
Claim 13
Dependent Claim
29 words
In a system for converting light to another energy form and containing a chemical energy converter, the improvement wherein said converter comprises a dimethine compound according to claim 1.
References Cited (Backward Citations)
US4018796A
Cited
US4105665A
Cited
US4258182A
Cited
US4268668A
Cited
US4319024A
Cited
US4312985A
Cited
US4316013A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-05-23 | 1986-11-22 | 1987-05-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-05-23 | 1990-11-22 | 1991-05-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-05-23 | 1994-11-22 | 1995-05-24 | $7700.00 | Window Closed / Lapsed |