Patent US2725618A successfully refreshed from Google Patents.
Patent US3979429A successfully refreshed from Google Patents.
US3979429A
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Para-amino-β-cyano-bis-styryl compounds
Assignee: Sandoz AG
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Filing: 1975-05-08
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Granted: 1976-09-07
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Expires: 1995-05-08
Abstract
Abstract The present invention relates to para-substituted-amino-β,β-dicyano- or β-cyano-,β-acyl-distyryl disperse dyes in which the benzene nuclei of the two styryl radicals are connected by a bridge member.
Inventors
- 👤 Ulrich Zirngibl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 04:56
CPC Classifications
D; D06; D06P; D06P1/00; D06P1/16; C; C09; C09B; C09B23/00; C09B23/14; C09B23/143; Y; Y10; Y10S; Y10S8/00; Y10S8/92; Y10S8/922
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
369 words
A compound of formula I, ##SPC7## in which each R 1 , independently, signifies (C 1-6 ) alkyl which is unsubstituted or monosubstituted by halogen, cyano, hydroxyl, alkoxy, phenyl, phenoxy or acyloxy, each R 2 , independently, signifies hydrogen, halogen, (C 1-6 ) alkyl or (C 1-6 ) alkoxy, R 3 signifies a divalent radical of formula --R 5 --R 7 --R 5 --R 7 --R 6 --R 7 --R 5 --R 7 --R 5 -- or R 5 --R 7 --R 6 --R 7 --R 5 -- in which R 6 signifies a direct bond or a divalent radical of formula --O--, --S--, --NR 9 --, --CO--, --O--CO--, --O--CO--O--, --SO 2 --, --NR 8 -- --CO--NR 8 -- or NR 8 --SO 2 --NR 8 , R 4 signifies cyano or acyl, each R 5 , independently, signifies a divalent radical of formula --NR 8 --CO--, --NR 8 --CO--O--, --O--SO 2 --, --NR 8 --SO 2 --, --O--SO 2 --NR 8 -- or has one of the significances given for R 6 , any unsymmetrical divalent radical as R 5 and R 6 being linked either way round, each R 7 , independently, signifies (C 1-6 ) alkylene or alkylidene, of up to 6 carbon atoms which alkylene and alkylidene radicals are unsubstituted or monosubstituted by halogen, cyano, hydroxyl, (C 1-6 ) alkoxy, phenyl, phenoxy or acyloxy, each R 8 , independently, signifies hydrogen, (C 1-6 ) alkyl or, when the chain contains any two R 8 attached to nitrogen atoms which are joined by an ethylene radical as R 7 , the two symbols R 8 , together with the nitrogen atoms and R 7 may join to form a piperazine ring, and R 9 signifies (C 1-6 ) alkylcarbonyl or (C 1-6 ) alkoxycarbonyl, any acyl group as R 4 or as part of an aryloxy group being of the formula R--Y or R'--Z in which R signifies (C 1-6 ) alkyl, Y signifies --O--CO--, --SO 2 -- or --O--SO 2 --, R' signifies hydrogen or (C 1-6 ) alkyl and Z signifies --CO--, --NR'--CO-- or --NR"--SO 2 -- in which R" has one of the significances of R', which molecule is free from acetal groups.
Claim 2
Dependent Claim
369 words
A compound of formula I, ##SPC7## in which each R 1 , independently, signifies (C 1-6 ) alkyl which is unsubstituted or monosubstituted by halogen, cyano, hydroxyl, alkoxy, phenyl, phenoxy or acyloxy, each R 2 , independently, signifies hydrogen, halogen, (C 1-6 ) alkyl or (C 1-6 ) alkoxy, R 3 signifies a divalent radical of formula --R 5 --R 7 --R 5 --R 7 --R 6 --R 7 --R 5 --R 7 --R 5 -- or R 5 --R 7 --R 6 --R 7 --R 5 -- in which R 6 signifies a direct bond or a divalent radical of formula --O--, --S--, --NR 9 --, --CO--, --O--CO--, --O--CO--O--, --SO 2 --, --NR 8 -- --CO--NR 8 -- or NR 8 --SO 2 --NR 8 , R 4 signifies cyano or acyl, each R 5 , independently, signifies a divalent radical of formula --NR 8 --CO--, --NR 8 --CO--O--, --O--SO 2 --, --NR 8 --SO 2 --, --O--SO 2 --NR 8 -- or has one of the significances given for R 6 , any unsymmetrical divalent radical as R 5 and R 6 being linked either way round, each R 7 , independently, signifies (C 1-6 ) alkylene or alkylidene, of up to 6 carbon atoms which alkylene and alkylidene radicals are unsubstituted or monosubstituted by halogen, cyano, hydroxyl, (C 1-6 ) alkoxy, phenyl, phenoxy or acyloxy, each R 8 , independently, signifies hydrogen, (C 1-6 ) alkyl or, when the chain contains any two R 8 attached to nitrogen atoms which are joined by an ethylene radical as R 7 , the two symbols R 8 , together with the nitrogen atoms and R 7 may join to form a piperazine ring, and R 9 signifies (C 1-6 ) alkylcarbonyl or (C 1-6 ) alkoxycarbonyl, any acyl group as R 4 or as part of an aryloxy group being of the formula R--Y or R'--Z in which R signifies (C 1-6 ) alkyl, Y signifies --O--CO--, --SO 2 -- or --O--SO 2 --, R' signifies hydrogen or (C 1-6 ) alkyl and Z signifies --CO--, --NR'--CO-- or --NR"--SO 2 -- in which R" has one of the significances of R', which molecule is free from acetal groups.
Claim 3
Dependent Claim
41 words
A compound according to claim 1, in which each R 1 , independently, signifies (C 1-4 ) alkyl or (C 1-4 ) alkyl monosubstituted by chlorine, bromine, hydroxy, (C 1-4 ) alkoxy, (C 1-4 ) alkylcarbonyloxy or (C 1-4 ) alkoxycarbonyloxy.
Claim 4
Dependent Claim
20 words
A compound according to claim 2, in which each R 2 , independently, signifies hydrogen or (C 1-4 ) alkyl.
Claim 5
Dependent Claim
39 words
A compound according to claim 3, in which R 6 signifies a direct bond or --O--, --S--, --NR 9 ' --, --O--CO-- or --O--CO--O-- in which R 9 ' signifies (C 1-4 ) alkylcarbonyl or (C 1-4 ) alkoxycarbonyl.
Claim 6
Dependent Claim
96 words
A compound according to claim 4, in which R 5 , independently, signifies one of the significances given to R 6 in claim 4 or --NR 8 ' CO--, --NR 8 ' CO--O--, --O--SO 2 --, --NR 8 ' SO 2 -- or O--SO 2 --NR 8 ' -- in which each R 8 ' , independently, signifies hydrogen or (C 1-4 ) alkyl, or any two R 8 's, when attached to nitrogen atoms connected by an ethylene radical as R 7 , together with nitrogen atoms and the ethylene radical, form a piperazine ring.
Claim 7
Dependent Claim
38 words
A compound according to claim 5, in which R 7 signifies an alkylene or alkylidene radical of up to 6 carbon atoms, unsubstituted or monosubstituted by hydroxy, chlorine, bromine, (C 1-4 ) alkoxy or (C 1-4 ) alkylcarbonyloxy.
Claim 8
Dependent Claim
17 words
A compound according to claim 6, in which R 4 signifies cyano or (C 1-4 ) alkoxycarbonyl.
Claim 9
Dependent Claim
15 words
A compound according to claim 1, in which the bridge member R 3 is symmetrical.
Claim 10
Dependent Claim
158 words
A compound according to claim 1, in which R 3 signifies a radical of formula --R 13 --R 15 --R 14 --R 15 --R 13 -- or --R 16 --R 14 --R 16 -- in which each R 13 , independently, signifies an alkylene radical of up to 6 carbon atoms, R 14 signifies an alkylene radical of 2 to 6 carbon atoms or an alkylene radical of 2 to 6 carbon atoms containing an ether linkage, each R 15 , independently, signifies --O--, --O--CO--, --O--CO--O--, --CO--NR 17 -- or --O--CO--NR 17 --, in which R 17 signifies hydrogen or (C 1-2 ) alkyl, each R 16 , independently, signifies one of the significances given for R 15 or signifies --O--SO 2 --, --NR 17 --SO 2 -- or --O--SO 2 --NR 17 -- in which R 17 is as defined above, any unsymmetrical divalent radical as R 15 or R 16 can be bonded either way round.
Claim 11
Dependent Claim
22 words
A compound according to claim 9, in which the two symbols R 13 , R 15 and R 16 are the same.
Claim 12
Dependent Claim
264 words
A compound according to claim 1, in which each R 1 , independently, signifies (C 1-4 ) alkyl or (C 1-4 ) alkyl monosubstituted by chlorine bromine, hydroxy, (C 1-4 ) alkoxy, (C 1-4 ) alkylcarbonyloxy or (C 1-4 ) alkoxycarbonyloxy, R 2 signifies hydrogen or (C 1-4 ) alkyl, R 3 signifies --R 5 ' --R 7 ' --R 5 ' --R 7 ' --R 6 ' --R 7 ' --R 5 ' --R 7 ' --R 5 ' -- or R 5 ' --R 7 ' --R 6 ' --R 7 ' --R 5 ' -- R 4 signifies cyano or (C 1-4 ) alkoxycarbonyl, R 6 ' signifies a direct bond or --O--, --S--, --NR 9 ' --, --O--CO-- or --O--CO--O in which R 9 ' signifies (C 1-4 ) alkylcarbonyl or (C 1-4 ) alkoxycarbonyl, each R 5 ' , independently, signifies one of the significances given for R 6 ' , or --NR 8 ' --CO--, --NR 8 --CO--O--, --O--SO 2 --, NR 8 ' --SO 2 -- or --O--SO 2 --NR 8 -- in which each R 8 ' , independently, signifies hydrogen or (C 1-4 ) alkyl or any two symbols R 8 ' , when attached to nitrogen atoms connected by an ethylene radical a R 7 , together with the nitrogen atoms and the ethylene radical as R 7 , signify a piperazine ring, and each R 7 ' , independently, signifies an alkylene or alkylidene radical which is unsubstituted or monosubstituted by hydroxy, chlorine, bromine, (C 1-4 ) alkoxy, or (C 1-4 ) alkylcarbonyloxy.
Claim 13
Dependent Claim
19 words
A compound according to claim 11, in which R 3 is symmetrical and R 6 is a direct bond.
Claim 14
Dependent Claim
20 words
A compound according to claim 11, in which R 3 is bound in a position ortho to the methine group.
Claim 15
Dependent Claim
61 words
A compound according to claim 9, of formula Ia, ##SPC8## in which the symbols R 11 are the same and signify (C 2-4 ) alkyl, and, R 12 signifies --R 13 --R 15 --R 14 --R 15 --R 13 -- or --R 16 --R 14 --R 16 -- in which R 13 to R 16 are as defined in claim 9.
Claim 16
Dependent Claim
30 words
A compound according to claim 11 in which R 1 signifies ethyl, R 2 signifies hydrogen, R 3 signifies a 5 to 12 membered chain and R 4 signifies cyano.
Claim 17
Dependent Claim
22 words
A compound according to claim 14, in which R 11 signifies ethyl and R 12 signifies a 5 to 12 membered chain.
Claim 18
Dependent Claim
34 words
A compound according to claim 14, in which R 12 signifies --CH 2 --X--(CH 2 ) n --X--CH 2 -- in which X signifies --O--CO-- or O--CO--O and n signifies 2, 4 or 6.
Claim 19
Dependent Claim
12 words
A compound according to claim 14 in which R 12 is symmetrical.
Claim 20
Dependent Claim
12 words
A compound according to claim 16, in which R 12 is symmetrical.
Claim 21
Dependent Claim
9 words
A compound according to claim 17, of formula ##SPC9##
Claim 22
Dependent Claim
9 words
A compound according to claim 17, of formula ##SPC10##
Claim 23
Dependent Claim
9 words
A compound according to claim 11, of formula ##SPC11##
Claim 24
Dependent Claim
9 words
A compound according to claim 17, of formula ##SPC12##
Claim 25
Dependent Claim
9 words
A compound according to claim 17, of formula ##SPC13##
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-09-07 | 1980-03-08 | 1980-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-07 | 1984-03-08 | 1984-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-07 | 1988-03-08 | 1988-09-07 | $7700.00 | Window Closed / Lapsed |