US4268438A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Cationic 1,3,4-thiadiazole dyestuffs
Assignee: Bayer AG
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Filing: 1979-03-13
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Granted: 1981-05-19
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Expires: 1999-03-13
Abstract
Abstract Cationic 1,3,4-thiadiazole dyestuffs of the general formula ##STR1## wherein R denotes hydrogen or an alkyl, alkenyl, acyl, cycloalkyl, aryl, aralkyl, amino, alkylamino, dialkylamino, arylamino, aralkylamino or heterocyclic radical and R 1 denotes hydrogen or an alkyl, alkenyl or aralkyl radical, or R and R 1 are linked to form a heterocyclic ring, with the condition that if R denotes aryl, R 1 cannot be hydrogen. R 2 denotes an alkyl, alkenyl, alkinyl or aralkyl radical, K denotes a radical of a coupling component and An.sup.(-) denotes an anion, are suitable for the dyeing and printing of natural and synthetic materials, in particular of polyacrylnitrile and acid-modified polyesters and polyamides.
Inventors
- 👤 Hauke Furstenwerth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 10:53
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125; C07D285/135; C09; C09B; C09B44/00; C09B44/10; C09B44/107
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
482 words
A cationic dyestuff of the formula ##STR343## wherein R 14 denotes H, --CH 3 , C 2 H 5 , --C 3 H 7 , iso--C 3 H 7 , --C 4 H 9 , iso--C 4 H 9 , sec.--C 4 H 9 , tert.--C 4 H 9 , ##STR344## --C 2 H 4 OH, --CH 2 --CHOH--CH 3 , --C 2 H 4 CN, --C 6 H 11 , --C 5 H 9 , --CH 2 --C 6 H 5 , --C 6 H 5 , --C 6 H 4 Cl--(p), C 6 H 3 Cl 2 --(2,5), C 6 H 4 --CH 3 --(o, m or p), --C 6 H 4 --OCH 3 --(p), --C 2 H 4 --O--CH 3 , C 2 H 4 --O--C 2 H 5 , ##STR345## -- Cl--C 6 H 4 --CO, -- CH 3 --C 6 H 4 --CO, C 2 H 5 OCO--, CH 3 OCO--, C 2 H 5 NHCO--, (C 2 H 5 ) 2 NCO--, (C 2 H 5 ) 2 NSO 2 --, CH 3 NHSO 2 -- or H 2 NCO--, R 15 denotes --CH 3 , --C 2 H 5 , --C 3 H 7 , iso--C 3 H 7 , --C 4 H 9 , iso--C 4 H 9 , sec.--C 4 H 9 , tert.--C 4 H 9 , ##STR346## --C 2 H 4 OH, --CH 2 --CHOH--CH 3 , --C 2 H 4 CN, --C 6 H 11 , --C 5 H 9 , --C 2 H 4 --O--CH 3 or --C 2 H 4 --O--C 2 H 5 , R 16 denotes alkyl with 1-4 C atoms, 2-cyanoethyl, 2-carbamoylethyl, 2-hydroxyethyl or benzyl, K 2 is a coupling component of the formula ##STR347## wherein R 17 denotes hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or bromine, R 18 denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, R 19 denotes hydrogen, alkyl with 1-4 C atoms, alkyl with 1-4 C atoms substituted by hydroxy or C 1-4 -alkoxy, or benzyl and R 20 denotes hydrogen, alkyl with 1-4 C atoms, alkyl with 1-4 C atoms substituted by hydroxy or C 1-4 -alkoxy, benzyl or phenyl, or R 19 and R 20 , together with the N atom bonded to them, represent a saturated heterocyclic ring which can contain further hetero-atoms, or R 18 and R 19 and/or R 20 and R 21 together form a radical of the formula ##STR348## wherein the C atom marked x is bonded to the N atom, R 21 denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy R 22 denotes methyl, ethyl or phenyl, R 23 denotes hydrogen, methyl, β-cyanoethyl, β-carbamoylethyl and β-carboxyethyl, R 24 denotes hydrogen, methyl, ethyl, benzyl or phenyl which is optionally substituted by chlorine, methyl, methoxy or nitro, R 25 denotes hydrogen, methyl, halogen, cyano or methoxycarbonyl, and Anθ denotes an anion.
Claim 2
Dependent Claim
482 words
A cationic dyestuff of the formula ##STR343## wherein R 14 denotes H, --CH 3 , C 2 H 5 , --C 3 H 7 , iso--C 3 H 7 , --C 4 H 9 , iso--C 4 H 9 , sec.--C 4 H 9 , tert.--C 4 H 9 , ##STR344## --C 2 H 4 OH, --CH 2 --CHOH--CH 3 , --C 2 H 4 CN, --C 6 H 11 , --C 5 H 9 , --CH 2 --C 6 H 5 , --C 6 H 5 , --C 6 H 4 Cl--(p), C 6 H 3 Cl 2 --(2,5), C 6 H 4 --CH 3 --(o, m or p), --C 6 H 4 --OCH 3 --(p), --C 2 H 4 --O--CH 3 , C 2 H 4 --O--C 2 H 5 , ##STR345## -- Cl--C 6 H 4 --CO, -- CH 3 --C 6 H 4 --CO, C 2 H 5 OCO--, CH 3 OCO--, C 2 H 5 NHCO--, (C 2 H 5 ) 2 NCO--, (C 2 H 5 ) 2 NSO 2 --, CH 3 NHSO 2 -- or H 2 NCO--, R 15 denotes --CH 3 , --C 2 H 5 , --C 3 H 7 , iso--C 3 H 7 , --C 4 H 9 , iso--C 4 H 9 , sec.--C 4 H 9 , tert.--C 4 H 9 , ##STR346## --C 2 H 4 OH, --CH 2 --CHOH--CH 3 , --C 2 H 4 CN, --C 6 H 11 , --C 5 H 9 , --C 2 H 4 --O--CH 3 or --C 2 H 4 --O--C 2 H 5 , R 16 denotes alkyl with 1-4 C atoms, 2-cyanoethyl, 2-carbamoylethyl, 2-hydroxyethyl or benzyl, K 2 is a coupling component of the formula ##STR347## wherein R 17 denotes hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or bromine, R 18 denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, R 19 denotes hydrogen, alkyl with 1-4 C atoms, alkyl with 1-4 C atoms substituted by hydroxy or C 1-4 -alkoxy, or benzyl and R 20 denotes hydrogen, alkyl with 1-4 C atoms, alkyl with 1-4 C atoms substituted by hydroxy or C 1-4 -alkoxy, benzyl or phenyl, or R 19 and R 20 , together with the N atom bonded to them, represent a saturated heterocyclic ring which can contain further hetero-atoms, or R 18 and R 19 and/or R 20 and R 21 together form a radical of the formula ##STR348## wherein the C atom marked x is bonded to the N atom, R 21 denotes hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy R 22 denotes methyl, ethyl or phenyl, R 23 denotes hydrogen, methyl, β-cyanoethyl, β-carbamoylethyl and β-carboxyethyl, R 24 denotes hydrogen, methyl, ethyl, benzyl or phenyl which is optionally substituted by chlorine, methyl, methoxy or nitro, R 25 denotes hydrogen, methyl, halogen, cyano or methoxycarbonyl, and Anθ denotes an anion.
Claim 3
Dependent Claim
57 words
A dyestuff according to claim 1, wherein R 14 , R 15 and R 16 each independently is C 1-4 -alkyl, R 17 is hydrogen or methyl, R 18 and R 21 are hydrogen, and R 19 and R 20 each independently is C 1-4 -alkyl or C 1-4 -alkyl substituted by hydroxy or C 1-4 -alkoxy.
Claim 4
Dependent Claim
26 words
A dyestuff according to claim 2, wherein R 18 and R 19 together form ##STR349## The C atom marked * being bonded to the N atom.
Claim 5
Dependent Claim
10 words
A dyestuff according to claim 2, of the formula ##STR350##
Claim 6
Dependent Claim
10 words
A dyestuff according to claim 2, of the formula ##STR351##
Claim 7
Dependent Claim
10 words
A dyestuff according to claim 2, of the formula ##STR352##
Claim 8
Dependent Claim
10 words
A dyestuff according to claim 2, of the formula ##STR353##
Claim 9
Dependent Claim
10 words
A dyestuff according to claim 2, of the formula ##STR354##
Claim 10
Dependent Claim
10 words
A dyestuff according to claim 2, of the formula ##STR355##
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-05-18 | 1984-11-17 | 1985-05-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-18 | 1988-11-17 | 1989-05-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-18 | 1992-11-17 | 1993-05-19 | $7700.00 | Window Closed / Lapsed |