US4619992A
Expired / Lapsed
US
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3-(β-aminoethyl)-4-cyano-isothiazolylazo dyes
Assignee: BASF SE
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Filing: 1985-03-12
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Granted: 1986-10-28
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Expires: 2005-03-12
Abstract
Abstract A compound of the formula: ##STR1## where R is hydrogen, C 1 -C 4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R 1 is allyl, C 1 -C 8 -alkyl, C 1 -C 8 -alkyl substituted by C 1 -C 8 -alkoxy, phenoxy, phenyl or C 1 -C 8 -alkanoyloxy, cyclopentyl, cyclohexyl, methylcyclohexyl, norbornyl, phenyl or phenyl substituted by chlorine, methyl or alkoxy; R 2 is C 1 -C 10 -alkanoyl, C 1 -C 10 -alkanoyl substituted by alkoxy or phenoxy, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C 1 -C 8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH 3 NHCO, C 2 H 5 NHCO, C 3 H 7 NHCO, C 4 H 9 NHCO, (CH 3 ) 2 NCO, CH 3 SO 2 , C 6 H 5 SO 2 or p--CH 3 --C 6 H 4 --SO 2 ; or R 1 and R 2 , together with the nitrogen atom, form a ring system, and K is a radical of a coupling component. The isothiazolylylazo compound of the invention is useful for the dyeing of the polyesters, nylon, and cellulose esters.
Inventors
- 👤 Udo Bergmann
- 👤 Johannes P. Dix
- 👤 Guenter Hansen
- 👤 Ernst Schefczik
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 14:35
CPC Classifications
C; C09; C09B; C09B29/00; C09B29/0025; C09B29/0074; C09B29/0077; C09B29/0081
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
174 words
A compound of the formula: ##STR213## where R is hydrogen, C 1 -C 4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R 1 is allyl, C 1 -C 8 -alkyl, C 1 -C 8 -alkyl substituted by C 1 -C 8 -alkoxy, phenoxy, phenyl or C 1 -C 8 -alkanoyloxy, cyclopentyl, cyclohexyl, and methylcyclohexyl, norbornyl, phenyl or phenyl substituted by chlorine, methyl or alkoxy; R 2 is C 1 -C 10 -alkanoyl, C 1 -C 10 -alkanoyl substituted by alkoxy or phenoxy, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C 1 -C 8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH 3 NHCO, C 2 H 5 NHCO, C 3 H 7 NHCO, C 4 H 9 NHCO, (CH 3 ) 2 NCO, CH 3 SO 2 , C 6 H 5 SO 2 or p--CH 3 --C 3 H 4 --SO 2 ; or R 1 and R 2 , together with the nitrogen atom, form a ring system selected from the group consisting of: ##STR214## and K is a radical of a coupling component.
Claim 2
Dependent Claim
174 words
A compound of the formula: ##STR213## where R is hydrogen, C 1 -C 4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R 1 is allyl, C 1 -C 8 -alkyl, C 1 -C 8 -alkyl substituted by C 1 -C 8 -alkoxy, phenoxy, phenyl or C 1 -C 8 -alkanoyloxy, cyclopentyl, cyclohexyl, and methylcyclohexyl, norbornyl, phenyl or phenyl substituted by chlorine, methyl or alkoxy; R 2 is C 1 -C 10 -alkanoyl, C 1 -C 10 -alkanoyl substituted by alkoxy or phenoxy, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C 1 -C 8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH 3 NHCO, C 2 H 5 NHCO, C 3 H 7 NHCO, C 4 H 9 NHCO, (CH 3 ) 2 NCO, CH 3 SO 2 , C 6 H 5 SO 2 or p--CH 3 --C 3 H 4 --SO 2 ; or R 1 and R 2 , together with the nitrogen atom, form a ring system selected from the group consisting of: ##STR214## and K is a radical of a coupling component.
Claim 3
Dependent Claim
227 words
The compound as claimed in claim 1, wherein KH is of the formula: ##STR215## where R 3 is hydrogen, alkyl, aralkyl or aryl, R 4 is hydrogen or R 5 , where R 5 is C 1 -C 6 -alkyl, or C 1 -C 6 -alkyl substituted by chlorine, bromine, hydroxyl, C 1 -C 8 -alkoxy, phenoxy, cyano, carboxyl, C 1 -C 8 -alkanoyloxy, C 1 -C 8 -alkoxy-C 1 -C 4 -alkoxy, benzoyloxy, o-, m- or p-methylbenzoyloxy, o-, m- or p-chlorobenzoyloxy, C 1 -C 8 -alkoxyalkanoyloxy, phenoxyalkanoyloxy, C 1 -C 8 -alkoxycarbonyloxy, C 1 -C 8 -alkoxyalkoxycarbonyloxy, benzyloxycarbonyloxy, phenethyloxycarbonyloxy, phenoxyethoxycarbonyloxy, C 1 -C 8 -alkylaminocarbonyloxy, cyclohexyl-aminocarbonyloxy, phenylamino-carbonyloxy, C 1 -C 8 -alkoxy-carbonyl, C 1 -C 8 -alkoxyalkoxy-carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C 1 -C 4 -alkoxy or phenethyloxycarbonyl, or phenyl, benzyl, phenethyl or cyclohexyl, R 6 and R 7 are each hydrogen, alkyl, alkoxy, phenoxy, halogen, alkylsulfonylamino, dialkylaminosulfonylamino, benzyloxy, benzylamino or C 1 -C 6 -alkanoylamino, R 8 is cyano, carbamyl, nitro or carbalkoxy, and R 9 is C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonylmethyl, cyanomethyl, benzyl or phenyl which is monosubstituted or polysubstituted by C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, phenoxy, benzyloxy, phenyl, chlorine, bromine, nitro, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -mono- or di-alkylamino, C 1 -C 4 -alkoxyethoxy, C 1 -C 4 -alkyl- or phenyl-mercapto.
Claim 4
Dependent Claim
73 words
The compound as claimed in claim 2, wherein said R 5 substituent is methyl, ethyl, propyl, butyl, pentyl, hexyl, allyl, methallyl, 2-chloroethyl, 2-bromoethyl, 2-cyanoethyl, 2-hydroxyethyl, 2-phenyl-2-hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxy-propyl, 2-hydroxy-butyl, 2-hydroxy-3-phenoxypropyl, 2-hydroxy-3-methoxypropyl, 2-hydroxy-3-butoxypropyl, 3-hydroxypropyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-phenoxyethyl, 2-phenoxypropyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-isobutyryloxyethyl, 2-methoxymethylcarbonyloxyethyl, 2-ethoxymethylcarbonyloxyethyl, 2-phenoxymethylcarbonyloxyethyl, 2-methoxycarbonyloxyethyl, 2-ethoxycarbonyloxyethyl, 2-propoxycarbonyloxyethyl, 2-butoxycarbonyloxyethyl, 2-phenyloxycarbonyloxyethyl, 2-benzyloxycarbonyloxyethyl, 2-methoxyethoxycarbonyloxyethyl, 2-ethoxyethoxycarbonyl-oxyethyl, 2-propoxyethoxycarbonyloxyethyl, 2-butoxyethoxycarbonyloxyethyl, 2-methylaminocarbonyl-oxyethyl, 2-ethyl-aminocarbonyloxyethyl, 2-propylaminocarbonyloxyethyl, 2-butylaminocarbonyloxyethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-propoxycarbonylethyl, 2-butoxycarbonylethyl, 2-phenoxycarbonylethyl, 2-benzyloxycarbonyl-ethyl, 2-β-phenyloxycarbonylethyl, 2-methoxyethoxycarbonylethyl, 2-ethoxyethoxycarbonylethyl, 2-propoxyethoxycarbonylethyl, 2-butoxyethoxycarbonylethyl or 2-phenoxyethoxycarbonylethyl.
Claim 5
Dependent Claim
210 words
A compound of the formula: ##STR216## where R is hydrogen, C 1 -C 4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R 1 is methyl, ethyl, propyl, butyl, hexyl, octyl, C 2 H 5 -OCH 2 CH 2 , CH 3 OCH 2 CH 2 CH 2 --, C 4 H 9 OCH 2 CH 2 CH 2 --, C 6 H 5 OCH 2 CH 2 --, C 6 H 5 OCH 2 CH 2 OCH 2 CH 2 CH 2 --, C 6 H 5 CH 2 -- or C 6 H 5 CH 2 CH 2 --; R 2 is C 1 -C 10 -alkanoyl C 1 -C 10 -alkanoyl substituted by alkoxy or phenoxyl, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C 1 -C 8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH 3 NHCO, C 2 H 5 NHCO, C 3 H 7 NHCO, C 4 H 9 NHCO, (CH 3 ) 2 NCO, CH 3 SO 2 , C 6 H 5 SO 2 or p--CH 3 --C 6 H 4 --SO 2 ; or R 1 and R 2 , together with the nitrogen atom, form a ring system selected from the group consisting of: ##STR217## and K is a radical of a coupling component.
Claim 6
Dependent Claim
210 words
A compound of the formula: ##STR216## where R is hydrogen, C 1 -C 4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R 1 is methyl, ethyl, propyl, butyl, hexyl, octyl, C 2 H 5 -OCH 2 CH 2 , CH 3 OCH 2 CH 2 CH 2 --, C 4 H 9 OCH 2 CH 2 CH 2 --, C 6 H 5 OCH 2 CH 2 --, C 6 H 5 OCH 2 CH 2 OCH 2 CH 2 CH 2 --, C 6 H 5 CH 2 -- or C 6 H 5 CH 2 CH 2 --; R 2 is C 1 -C 10 -alkanoyl C 1 -C 10 -alkanoyl substituted by alkoxy or phenoxyl, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C 1 -C 8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH 3 NHCO, C 2 H 5 NHCO, C 3 H 7 NHCO, C 4 H 9 NHCO, (CH 3 ) 2 NCO, CH 3 SO 2 , C 6 H 5 SO 2 or p--CH 3 --C 6 H 4 --SO 2 ; or R 1 and R 2 , together with the nitrogen atom, form a ring system selected from the group consisting of: ##STR217## and K is a radical of a coupling component.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-10-27 | 1990-04-28 | 1990-10-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-10-27 | 1994-04-28 | 1994-10-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-10-27 | 1998-04-28 | 1998-10-28 | $7700.00 | Window Closed / Lapsed |