US3987026A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Transiently water-soluble non-heterocyclic azo and disazo disperse dyestuffs
Assignee: Novartis Corp
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Filing: 1973-07-25
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Granted: 1976-10-19
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Expires: 1993-07-25
Abstract
Abstract Transiently water-soluble dyestuffs of the formula ##EQU1## WHEREIN F is a radical of a non-heterocyclic azo disperse dyestuff containing no groups which dissociate in water, n is 1 or 2, X is an electrophilic group, R 1 is an optionally substituted ethylene group, and R 2 and R 3 are alkyl radicals which are different from each other and which carry altogether at least one water-solubilizing group and optionally still further substituents which do not impart solubility in water and R 3 can furthermore be a hydrogen atom. The dyestuffs can be dissolved in aqueous dyeing baths and dye polyester fibers in yellow, red and blue shades of good fastness.
Inventors
- 👤 Stefan Koller
- 👤 Peter Aeschlimann
- 👤 Hans Scheidegger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 01:49
CPC Classifications
C; C09; C09B; C09B43/00; C09B29/00; C09B31/00; C09B5/00; C09B5/02; C09B62/00; C09B62/44; C09B62/443; C09B69/00
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
362 words
A dyestuff of the formula ##SPC47## in which D is phenyl which is unsubstituted or substituted by chloro, bromo, nitro, cyano, thiocyano, trifluoromethyl, lower alkyl, lower alkoxy, phenoxy, lower alkylmercapto, loweralkoxycarbonyl, loweralkoxycarbonyloxy, loweralkoxysulphonyl, aminosulphonyloxy, aminocarbonyl, benzoyl, 4-chlorobenzoyl, 4-methylbenzoyl, benzenesulphonyl, acetyl, propionyl, chloroacetyl, methylsulphonyl, benzoylamino, 4-chlorobenzoylamino, 4-methylbenzoylamino, benzenesulphonylamino, acetylamino, propionylamino, chloroacetylamino, methylsulphonylamino; phenylazo which is unsubstituted or substituted by chloro, nitro lower alkyl, or lower alkoxy or ##EQU2## wherein, R' 1 and R' 2 are hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkyl substituted by chlorine, fluorine, bromine, cyano, cyanoethoxy, hydroxy, lower alkoxy, lower alkylcarbonyloxy, lower alkylcarbonylamino, benzoyloxy, benzoylamino, lower alkoxycarbonyloxy, phenoxycarbonyloxy, phenylaminocarbonyloxy, lower alkylaminocarbonyloxy, or ##EQU3## wherein X is --NH--CO--, --NH--SO 2 --, --SO 2 --, --CO--, --O--CO, --N(lower alkyl)--SO 2 -- or --N(lower alkyl)--CO--, R 1 is ethylene or 1,2-propylene, R 2 is hydrogen, C 1 -C 8 -alkyl or the same as R 3 , R 3 is C 1 -C 5 --alkylene--O--SO 3 H, C 1 -C 5 --alkylene--SO 3 H, C 1 -C 5 -- alkylene--O--PO 3 H 2 and ##EQU4## c and d are hydrogen, chlorine, lower alkoxy, lower alkyl, phenylthio, phenoxy and lower alkyloxycarbonyl, and c is also bromine, trifluoromethyl, acylamino and N-methyl acylamino wherein "acyl" is lower alkanoyl, lower alkoxycarbonyl, phenoxycarbonyl, lower alkylaminocarbonyl, phenylaminocarbonyl, --CO--R 1 --NR 2 R 3 and --SO 2 --R 1 --NR 1 R 2 , R' 1 and R' 2 each are C 1 -C 4 -alkyl and C 1 -C 4 -alkyl substituted by chlorine, bromine, cyano, cyanoethoxy, hydroxy, phenyl, lower alkoxy, lower alkylcarbonyloxy and ##EQU5## wherein X is --SO 2 --, --NH--SO 2 -- or --NH--CO--, and R 1 is ethylene or 1,2-propylene, R 2 is C 1 --C 4 --alkyl or the same as R 3 , R 3 is C 1 -C 4 --alkylene--O--SO 3 H, and C 1 -C 4 --alkylene--SO 3 H, c and d are hydrogen, chlorine, lower alkoxy, lower alkyl, and c is also lower alkanoylamino and --HN--CO--R 1 --NR 2 R 3 , and wherein at least one of the phenyl group D, A or R' 1 or R' 2 contains a group of the formula ##EQU6##
Claim 2
Dependent Claim
362 words
A dyestuff of the formula ##SPC47## in which D is phenyl which is unsubstituted or substituted by chloro, bromo, nitro, cyano, thiocyano, trifluoromethyl, lower alkyl, lower alkoxy, phenoxy, lower alkylmercapto, loweralkoxycarbonyl, loweralkoxycarbonyloxy, loweralkoxysulphonyl, aminosulphonyloxy, aminocarbonyl, benzoyl, 4-chlorobenzoyl, 4-methylbenzoyl, benzenesulphonyl, acetyl, propionyl, chloroacetyl, methylsulphonyl, benzoylamino, 4-chlorobenzoylamino, 4-methylbenzoylamino, benzenesulphonylamino, acetylamino, propionylamino, chloroacetylamino, methylsulphonylamino; phenylazo which is unsubstituted or substituted by chloro, nitro lower alkyl, or lower alkoxy or ##EQU2## wherein, R' 1 and R' 2 are hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkyl substituted by chlorine, fluorine, bromine, cyano, cyanoethoxy, hydroxy, lower alkoxy, lower alkylcarbonyloxy, lower alkylcarbonylamino, benzoyloxy, benzoylamino, lower alkoxycarbonyloxy, phenoxycarbonyloxy, phenylaminocarbonyloxy, lower alkylaminocarbonyloxy, or ##EQU3## wherein X is --NH--CO--, --NH--SO 2 --, --SO 2 --, --CO--, --O--CO, --N(lower alkyl)--SO 2 -- or --N(lower alkyl)--CO--, R 1 is ethylene or 1,2-propylene, R 2 is hydrogen, C 1 -C 8 -alkyl or the same as R 3 , R 3 is C 1 -C 5 --alkylene--O--SO 3 H, C 1 -C 5 --alkylene--SO 3 H, C 1 -C 5 -- alkylene--O--PO 3 H 2 and ##EQU4## c and d are hydrogen, chlorine, lower alkoxy, lower alkyl, phenylthio, phenoxy and lower alkyloxycarbonyl, and c is also bromine, trifluoromethyl, acylamino and N-methyl acylamino wherein "acyl" is lower alkanoyl, lower alkoxycarbonyl, phenoxycarbonyl, lower alkylaminocarbonyl, phenylaminocarbonyl, --CO--R 1 --NR 2 R 3 and --SO 2 --R 1 --NR 1 R 2 , R' 1 and R' 2 each are C 1 -C 4 -alkyl and C 1 -C 4 -alkyl substituted by chlorine, bromine, cyano, cyanoethoxy, hydroxy, phenyl, lower alkoxy, lower alkylcarbonyloxy and ##EQU5## wherein X is --SO 2 --, --NH--SO 2 -- or --NH--CO--, and R 1 is ethylene or 1,2-propylene, R 2 is C 1 --C 4 --alkyl or the same as R 3 , R 3 is C 1 -C 4 --alkylene--O--SO 3 H, and C 1 -C 4 --alkylene--SO 3 H, c and d are hydrogen, chlorine, lower alkoxy, lower alkyl, and c is also lower alkanoylamino and --HN--CO--R 1 --NR 2 R 3 , and wherein at least one of the phenyl group D, A or R' 1 or R' 2 contains a group of the formula ##EQU6##
Claim 3
Dependent Claim
36 words
A dyestuff according to claim 1, wherein D corresponds to the formula ##STR73## in which the phenyl ring G is unsubstituted or substituted by lower alkyl, lower alkoxy, lower alkoxycarbonyl, chloro, bromo, methylsulfonyl, nitro or cyano.
Claim 4
Dependent Claim
15 words
A dyestuff according to claim 1 wherein the group ##STR74## corresponds to the formula ##STR75##
Claim 5
Dependent Claim
19 words
A dyestuff according to claim 3 wherein X is --HN--SO 2 --, --HN--CO--, --O--CO--, --SO 2 -- or --CO--.
Claim 6
Dependent Claim
108 words
A dyesfuff of the formula ##SPC48## wherein the phenylene ring E is unsubstituted or substituted by lower alkyl, lower alkoxy or nitro, the phenyl ring F is further unsubstituted or substituted by lower alkyl or lower alkoxy, the phenylene ring G' is unsubstituted or substituted by lower alkyl, lower alkoxy, lower alkoxycarbonyl, chloro, bromo, nitro or cyano; R 1 is ethylene or 1,2-propylene; R 2 is hydrogen, C 1 -C 8 alkyl or is the same as R 3 ; and R 3 is C 1 -C 5 --alkylene--O--SO 3 H, C 1 -C 5 --alkylene--SO 3 H, C 1 -C 5 --alkylene--O--PO 3 H 2 or ##STR76##
Claim 7
Dependent Claim
108 words
A dyesfuff of the formula ##SPC48## wherein the phenylene ring E is unsubstituted or substituted by lower alkyl, lower alkoxy or nitro, the phenyl ring F is further unsubstituted or substituted by lower alkyl or lower alkoxy, the phenylene ring G' is unsubstituted or substituted by lower alkyl, lower alkoxy, lower alkoxycarbonyl, chloro, bromo, nitro or cyano; R 1 is ethylene or 1,2-propylene; R 2 is hydrogen, C 1 -C 8 alkyl or is the same as R 3 ; and R 3 is C 1 -C 5 --alkylene--O--SO 3 H, C 1 -C 5 --alkylene--SO 3 H, C 1 -C 5 --alkylene--O--PO 3 H 2 or ##STR76##
Claim 8
Dependent Claim
35 words
A dyestuff according to claim 1, of the formula ##SPC49## wherein R' 1 and R' 2 are the same or different and are lower alkyl, phenylethyl, benzyl, cyanoethyl, lower alkylcarbonyloxy-lower alkyl, hydroxy-lower alkyl or cyanoethoxyethyl.
Claim 9
Dependent Claim
10 words
A dyestuff according to claim 1, of the formula ##SPC50##
Claim 10
Dependent Claim
16 words
A dyestuff according to claim 1, of the formula ##SPC51## wherein c represents hydrogen or halogen.
Claim 11
Dependent Claim
32 words
A dyestuff according to claim 1, of the formula ##SPC52## wherein R" 1 is lower alkyl, phenylethyl, benzyl, cyanoethyl, lower alkylcarbonyloxy-lower alkyl, hydroxy-lower alkyl, or cyanoethoxyethyl wherein c represents hydrogen or methyl.
Claim 12
Dependent Claim
14 words
A dyestuff according to claim 9, wherein R" 1 is a lower alkyl group.
Claim 13
Dependent Claim
13 words
A dyestuff according to claim 10, wherein D is 2-cyano-4-nitro-phenyl, 2-chloro-4-nitrophenyl or 2,6-dichloro-4-nitrophenyl.
Claim 14
Dependent Claim
29 words
A dyestuff according to claim 1, of the formula ##SPC53## wherein d is hydrogen or halogen, a lower alkyl, lower alkoxy, lower alkylmercapto, phenyl, phenoxy, phenylmercapto or lower alkoxycarbonyl.
Claim 15
Dependent Claim
10 words
A dyestuff according to claim 12, of the formula ##SPC54##
Claim 16
Dependent Claim
35 words
A dyestuff according to claim 13, of the formula ##SPC55## wherein R" 1 and R" 2 are the same or different and represent lower alkyl, phenylethyl, benzyl, cyanoethyl, hydroxy-lower alkyl, lower alkyloxycarbonyl-lower alkyl or cyanoethoxyethyl.
Claim 17
Dependent Claim
10 words
A dyestuff according to claim 14, of the formula ##SPC56##
Claim 18
Dependent Claim
12 words
A dyestuff according to claim 15, wherein D is 2-chloro-4-nitrophenyl or 2-cyano-4-nitrophenyl.
Claim 19
Dependent Claim
10 words
A dyestuff according to claim 7 of the formula ##SPC57##
Claim 20
Dependent Claim
10 words
A dyestuff according to claim 9 of the formula ##SPC58##
Claim 21
Dependent Claim
10 words
A dyestuff according to claim 15 of the formula ##SPC59##
References Cited (Backward Citations)
US3519642A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-10-19 | 1980-04-19 | 1980-10-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-10-19 | 1984-04-19 | 1984-10-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-10-19 | 1988-04-19 | 1988-10-19 | $7700.00 | Window Closed / Lapsed |