US4058516A
Expired / Lapsed
US
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Sulfo group-containing azo compounds having a tetrazo component radical derived from an optionally substituted 3,8-diaminodibenzofuran
Assignee: Sandoz AG
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Filing: 1974-06-20
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Granted: 1977-11-15
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Expires: 1994-06-20
Abstract
Abstract Dyes of the formula <IMAGE> AND SUBSTITUTED DERIVATIVES THEREOF, WHEREIN R is a coupling component radical, R1 is a coupling component radical, with the proviso that R and R1 are different, and N IS 1 TO 8, ARE DISCLOSED. They are useful for dyeing and printing natural and synthetic polyamides, cotton and other cellulosic fibers, polypropylene fibers modified by basic groups, synthetic polyamides and polyesters modified by acid groups, paper and leather. They exhibit good fastness to light, wet treatments and abrasion.
Inventors
- 👤 Roland Mislin
- 👤 Hanspeter Uehlinger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 18:26
CPC Classifications
C; C09; C09B; C09B45/00; C09B45/02; C09B45/24; C09B45/28; C09B35/00; C09B35/02; C09B35/039; C09B35/34; C09B35/36; C09B35/376; C09B35/38; C09B35/40; C09B62/00; C09B62/02; C09B62/04; C09B62/08; C09B62/09
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
283 words
A compound of the formula ##STR187## or a salt thereof, wherein (a) one of R 2a and R 3a is ##STR188## and the other is ##STR189## b. one of R 2a and R 3a is ##STR190## c. one of R 2a and R 3a is ##STR191## and the other is ##STR192## wherein R 4a is hydrogen, hydroxy, sulfo or ##STR193## R 5a is hydroxy, carboxy, amino, N-(C 1-4 alkyl)amino, N-phenylamino, N,N-di-(C 1-4 alkyl)amino, N-(C 1-4 alkyl) N-(C 1-4 alkyl)phenylamino, N-(C 1-4 alkyl)-N-benzylamino or N-(C 1-4 alkyl) N-(C 1-4 alkyl)phenylsulfamoyl, each R 6a is independently amino or hydroxy, each R 7a and R 8a is independently hydrogen, C 1-4 alkyl, halo or sulfo, each R 9a is independently hydrogen, C 1-4 alkyl, halo or cyano, R 10a is hydroxy, amino or acetamido, R 11a is hydrogen, carboxy or hydroxy, R 12a is hydrogen, sulfo, C 1-4 alkyl, C 1-4 alkylsulfonyl, C 1-4 alkoxy, C 1-4 alkylamino, phenylamino, (C 1-4 alkoxy)phenylamino or trimethylphenylamino, each of R 13a and R 14a is independently hydrogen or sulfo, each R 15a is independently 2-ethylhexyl, butyl, phenyl, (C 1-4 alkyl)phenyl, (C 1-4 -alkoxy)phenyl, di-(C 1-4 alkoxy)phenyl or disulfonaphthyl, R 16a is C 1-4 alkyl, phenylsulfonyl or (C 1-4 alkyl)phenylsulfonyl, R 18a is hydrogen or C 1-4 alkyl, R 19a is hydrogen or C 1-4 alkyl, R 20a is hydrogen, halo, C 1-4 alkyl or C 1-4 alkoxy, R 21a is hydrogen or sulfo, and R 22a is 4,6-dichloro-1,3,5-triazinyl-2,2,6-dichloropyrimidyl-4,2,5,6-trichloropyrimidyl-4,4-chloro-6-(4'-sulfophenylamino)-1,3,5-triazinyl-2,4-chloro-6-(phenylamino)-1,3,5-triazinyl-2 or 5-chloro-2,6-difluoropyrimidyl-4, and X is hydrogen or sulfo, with the provisos that (1) the compound contains 1, 2, 3 or 4 sulfo groups, (2) R 2a and R 3a are different, and (3) X is hydrogen when R 3a is ##STR194##
Claim 2
Dependent Claim
283 words
A compound of the formula ##STR187## or a salt thereof, wherein (a) one of R 2a and R 3a is ##STR188## and the other is ##STR189## b. one of R 2a and R 3a is ##STR190## c. one of R 2a and R 3a is ##STR191## and the other is ##STR192## wherein R 4a is hydrogen, hydroxy, sulfo or ##STR193## R 5a is hydroxy, carboxy, amino, N-(C 1-4 alkyl)amino, N-phenylamino, N,N-di-(C 1-4 alkyl)amino, N-(C 1-4 alkyl) N-(C 1-4 alkyl)phenylamino, N-(C 1-4 alkyl)-N-benzylamino or N-(C 1-4 alkyl) N-(C 1-4 alkyl)phenylsulfamoyl, each R 6a is independently amino or hydroxy, each R 7a and R 8a is independently hydrogen, C 1-4 alkyl, halo or sulfo, each R 9a is independently hydrogen, C 1-4 alkyl, halo or cyano, R 10a is hydroxy, amino or acetamido, R 11a is hydrogen, carboxy or hydroxy, R 12a is hydrogen, sulfo, C 1-4 alkyl, C 1-4 alkylsulfonyl, C 1-4 alkoxy, C 1-4 alkylamino, phenylamino, (C 1-4 alkoxy)phenylamino or trimethylphenylamino, each of R 13a and R 14a is independently hydrogen or sulfo, each R 15a is independently 2-ethylhexyl, butyl, phenyl, (C 1-4 alkyl)phenyl, (C 1-4 -alkoxy)phenyl, di-(C 1-4 alkoxy)phenyl or disulfonaphthyl, R 16a is C 1-4 alkyl, phenylsulfonyl or (C 1-4 alkyl)phenylsulfonyl, R 18a is hydrogen or C 1-4 alkyl, R 19a is hydrogen or C 1-4 alkyl, R 20a is hydrogen, halo, C 1-4 alkyl or C 1-4 alkoxy, R 21a is hydrogen or sulfo, and R 22a is 4,6-dichloro-1,3,5-triazinyl-2,2,6-dichloropyrimidyl-4,2,5,6-trichloropyrimidyl-4,4-chloro-6-(4'-sulfophenylamino)-1,3,5-triazinyl-2,4-chloro-6-(phenylamino)-1,3,5-triazinyl-2 or 5-chloro-2,6-difluoropyrimidyl-4, and X is hydrogen or sulfo, with the provisos that (1) the compound contains 1, 2, 3 or 4 sulfo groups, (2) R 2a and R 3a are different, and (3) X is hydrogen when R 3a is ##STR194##
Claim 3
Dependent Claim
23 words
A compound according to claim 1, or a salt thereof, with the proviso that the compound contains 2, 3 or 4 sulfo groups.
Claim 4
Dependent Claim
18 words
A compound according to claim 2, or a salt thereof, wherein R 2a or R 3a is ##STR195##
Claim 5
Dependent Claim
35 words
A compound according to claim 3, or a salt thereof, wherein ##STR196## wherein R 22a is 4,6-dichloro-1,3,5-triazinyl-2, 2,6-dichloropyrimidyl-4,2,5,6-trichloropyrimidyl-4,4-chloro-6-(4'-sulfophenylamino)-1,3,5-triazinyl-2,4-chloro-6-(phenylamino)-1,3,5-triazinyl-2 or 5-chloro-2,6-difluoropyrimidyl-4, R 44a is hydrogen, methyl, chloro or methoxy, and R 45a is hydrogen or methyl.
Claim 6
Dependent Claim
26 words
A compound according to claim 3, or a salt thereof, wherein ##STR197## wherein R 22a is 4,6-dichloro-1,3,5-triazinyl-2,2,6-dichloropyrimidyl-4,2,5,6-trichloropyrimidyl-4,4-chloro-6-(4'-sulfophenylamino)-1,3,5-triazinyl-2,4-chloro-6-(phenylamino)-1,3,5-triazinyl-2 or 5-chloro-2,6-difluoropyrimidyl-4, and R 46a is hydrogen or sulfo.
Claim 7
Dependent Claim
197 words
A compound according to claim 1 having the formula ##STR198## or a salt thereof, wherein one of R 2a and R 3a is ##STR199## wherein R 22a is 4,6-dichloro-1,3,5-triazinyl-2,2,6-dichloropyrimidyl-4,2,5,6-trichloropyrimidyl-4,4-chloro-6-(4'-sulfophenylamino)-1,3,5-triazinyl-2,4-chloro-6-(phenylamino)-1,3,5-triazinyl-2 or 5-chloro-2,6-difluoropyrimidyl-4, R 30a is hydroxy, carboxy, N-C 1-4 alkylamino, N,N-di-(C 1-4 alkyl)amino, N-phenylamino, N-(C 1-4 alkyl)-N-benzylamino, N-(C 1-4 alkyl)-N-(C 1-4 alkyl)phenylsulfamoyl or 2-hydroxy-5-sulfophenylazo, R 31a is hydrogen or hydroxy, with the proviso that R 31a is hydroxy when R 30a is hydroxy when R 30a is 2-hydroxy-5-sulfophenylazo, each of R 33a and R 35a is independently hydrogen or chloro, R 34a is hydrogen, sulfo or chloro, R 36a is hydroxy, amino or acetamido, R 37a is hydrogen, hydroxy, carboxy or sulfo, each of R 38a , R 39a and R 40a is independently hydrogen or sulfo, with the proviso that at least one and not more than three of R 37a , R 38a , R 39a and R 40a are sulfo, R 41a is pheny, methylphenyl, methoxyphenyl, dimethoxyphenyl, 2-ethylhexyl or disulfonaphthyl, R 42a is methyl, ethyl, phenylsulfonyl or p-methylphenylsulfonyl, R 43a is hydrogen or methyl, R 44a is hydrogen, methyl, chloro or methoxy, R 45a is hydrogen or methyl, and R 46a is hydrogen or sulfo.
Claim 8
Dependent Claim
23 words
A compound according to claim 6, or a salt thereof, with the proviso that the compound contains 2, 3 or 4 sulfo groups.
Claim 9
Dependent Claim
33 words
a compound according to claim 1, or a salt thereof, wherein at least one of R 2a and R 3a is ##STR200## with the proviso that R 2a and R 3a are different.
Claim 10
Dependent Claim
34 words
A compound according to claim 8, or a salt thereof, wherein each ##STR201## where each of R 33a and R 35a is independently hydrogen or chloro, and R 34a is hydrogen, sulfo or chloro.
Claim 11
Dependent Claim
23 words
A compound according to claim 8, or a salt thereof, with the proviso that the compound contains 2, 3 or 4 sulfo groups.
Claim 12
Dependent Claim
14 words
A compound according to claim 10, or a salt thereof, wherein X is hydrogen.
Claim 13
Dependent Claim
33 words
A compound according to claim 1, or a salt thereof, wherein at least one of R 2a and R 3a is ##STR202## with the proviso that R 2a and R 3a are different.
Claim 14
Dependent Claim
23 words
A compound according to claim 12, or a salt thereof, wherein each R 15a is independently phenyl, methylphenyl, methoxyphenyl, dimethoxyphenyl, 2-ethylhexyl or disulfonaphthyl.
Claim 15
Dependent Claim
18 words
A compound according to claim 1, or a salt thereof, wherein R 2a or R 3a is ##STR203##
Claim 16
Dependent Claim
18 words
A compound according to claim 1, or a salt thereof, wherein R 2a or R 3a is ##STR204##
Claim 17
Dependent Claim
28 words
A compound according to claim 15, or a salt thereof, wherein ##STR205## wherein R 42a is methyl, ethyl, phenylsulfonyl or p-methylphenylsulfonyl, and R 43a is hydrogen or methyl.
Claim 18
Dependent Claim
21 words
A compound according to claim 15, or a salt thereof, wherein ##STR206## wherein R 42a is methyl, ethyl, phenylsulfonyl or p-methylphenylsulfonyl.
Claim 19
Dependent Claim
25 words
A compound according to claim 15, or a salt thereof, wherein one of R 2a and R 3a is ##STR207## and the other is ##STR208##
Claim 20
Dependent Claim
70 words
A compound according to claim 18, or a salt thereof, wherein ##STR209## wherein R 36a is hydroxy, amino or acetamido, R 37a is hydrogen, hydroxy, carboxy or sulfo, and each of R 38a , R 39a and R 40a is independently hydrogen or sulfo, with the proviso that at least one and not more than three of R 37a , R 38a , R 39a and R 40a are sulfo.
Claim 21
Dependent Claim
23 words
A compound according to claim 18, or a salt thereof, with the proviso that the compound contains 2, 3 or 4 sulfo groups.
Claim 22
Dependent Claim
14 words
A compound according to claim 20, or a salt thereof, wherein X is hydrogen.
Claim 23
Dependent Claim
43 words
A compound according to claim 18, or a salt thereof, wherein one of R 2a and R 3a is 1-hydroxyl-3-sulfonaphthyl-2,1-hydroxy-3,6-disulfonaphthyl-2,1-hydroxy-3,6,8-trisulfonaphthyl-2,2-hydroxy-6-sulfonaphthyl-1,2-hydroxy-8-sulfonaphthyl-1,2-hydroxy-6,8-disulfonaphthyl-1,2-hydroxy-3,6,8-trisulfonaphthyl-1 or 2-amino-3,6-disulfonaphthyl-1, the other of R 2a and R 3a is 4-mothoxphenyl, 4-ethoxyphenyl, 4-phenylsulfonyloxyphenyl, 4-(4'-methylphenylsulfonyloxy)phenyl, 4-methoxy-2-methylphenyl, 4-ethoxy-2-methylphenyl or 2-methyl-4-(4'-methylphenylsulfonyloxy)phenyl, and X is hydrogen.
Claim 24
Dependent Claim
14 words
The compound according to claim 1 having the formula ##STR210## or a salt thereof.
Claim 25
Dependent Claim
14 words
The compound according to claim 3 having the formula ##STR211## or a salt thereof.
Claim 26
Dependent Claim
14 words
The compound according to claim 3 having the formula ##STR212## or a salt thereof.
Claim 27
Dependent Claim
14 words
The compound according to claim 3 having the formula ##STR213## or a salt thereof.
Claim 28
Dependent Claim
14 words
The compound according to claim 8 having the formula ##STR214## or a salt thereof.
Claim 29
Dependent Claim
14 words
The compound according to claim 8 having the formula ##STR215## or a salt thereof.
Claim 30
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR216## or a salt thereof.
Claim 31
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR217## or a salt thereof.
Claim 32
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR218## or a salt thereof.
Claim 33
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR219## or a salt thereof.
Claim 34
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR220## or a salt thereof.
Claim 35
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR221## or a salt thereof.
Claim 36
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR222## or a salt thereof.
Claim 37
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR223## or a salt thereof.
Claim 38
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR224## or a salt thereof.
Claim 39
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR225## or a salt thereof.
Claim 40
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR226## or a salt thereof.
Claim 41
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR227## or a salt thereof.
Claim 42
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR228## or a salt thereof.
Claim 43
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR229## or a salt thereof.
Claim 44
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR230## or a salt thereof.
Claim 45
Dependent Claim
14 words
The compound according to claim 18 having the formula ##STR231## or a salt thereof.
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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) | 1980-11-14 | 1981-05-16 | 1981-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-14 | 1985-05-16 | 1985-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-14 | 1989-05-16 | 1989-11-15 | $7700.00 | Window Closed / Lapsed |