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US5023324A
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Biscationic disazo and trisazo compounds having optionally further substituted 6-hydroxy-4-methy-3-N-pyridiniumpyridone-2 coupling component radicals, dyes compositions comprising them and their use
Assignee: Clariant Finance BVI Ltd
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Filing: 1986-07-29
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Granted: 1991-06-11
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Expires: 2006-07-29
Abstract
Abstract Disazo and trisazo compounds free of sulfo groups which contain 6-hydroxy-4-methyl-3-N-pyridiniumpyridone-2 coupling component radicals, the preferred compounds being of the formula <IMAGE> wherein R is a tetrazo component radical, each R1 is independently hydrogen, C1-4alkyl, C2-4hydroxyalkyl the hydroxy group of which is in other than the 1-position or -NR3R4, wherein each of R3 and R4 is independently n-C1-4alkyl, each R2 is independently hydrogen, n-C1-4alkyl, n-C1-4hydroxyalkyl or C1-4alkoxy, and each A(-) is an anion, and liquid and granulated dye compositions comprising such compounds, are useful for dyeing paper and basically dyeable substrates such as polymers and copolymers of acrylonitrile and dicyanoethylene and synthetic polyesters and polyamides modified to contain acid groups. Dyeings on paper are brilliant and possess good light fastness and good fastness to water and alcohol.
Inventors
- 👤 Helmut Moser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 14:27
CPC Classifications
C; C09; C09B; C09B44/00; C09B44/02; C09B44/08; C09B67/00; C09B67/0071; C09B67/0075; D; D06; D06P; D06P1/00; D06P1/02; D06P1/04; D06P1/08; D21; D21H; D21H21/00; D21H21/14; D21H21/28; Y; Y10; Y10S; Y10S8/00; Y10S8/916; Y10S8/919
Claims Analysis
Total Claims: 58
Claim 1
Independent Claim
259 words
A compound of the formula ##STR72## wherein R is 2,7-fluoroenylene, ##STR73## wherein Z is a direct bond, straight or branched C 1-6 alkylene, --CO--, --NHCSNH--, --S--, --O--, --CH═CH--, --S--S--, --SO 2 --, --NH--, --NH--CO--, --NCH 3 --CO--, ##STR74## --XO 2 NH--, ##STR75## --NR 8 --CO--(CH 2 ) n --CO--NR 8 --, --NR 8 --CO--CH═CH--CO--NR 8 --, --NR 8 --CO--NR 8 --, --CO--NH--NH--CO--, --CH 2 --CO--NH--NH--CO--CH 2 --, --CH═CH--CO--NH--NH--CO--CH═CH--, ##STR76## --O--CO--O--, --CO--O--, --CO--CO--, --O--(CH 2 ) n --O--, ##STR77## wherein each R 8 is independently hydrogen or C 1-4 alkyl, x is halo, C 1-4 alkyl or C 1-4 alkoxy, y is halo, --NHCH 2 CH 2 OH or --N(CH 2 CH 2 OH) 2 , and n is 1, 2, 3 or 4, with the proviso that Z is meta or para to each --N═N-- linkage, Zo is a direct bond, --N═N--, --CH 2 -- or --CH 2 CH 2 --, R 5 is hydrogen, halo, C 1-4 alkyl or C 1-4 alkoxy, R 6 is halo, C 1-4 alkyl or C 1-4 alkoxy, and R 7 is hydrogen, C 1-4 alkyl or C 1-4 alkoxy, each R 1 is independently hydrogen, C 1-4 alkyl, C 2-4 hydroxyalkyl the hydroxy group of which is in other than the 1-position or --NR 3 R 4 , wherein each of R 3 and R 4 is independently n-C 1-4 alkyl, each R 2 is independently hydrogen, n-C 1-4 alkyl, n-C 1-4 -hydroxyalkyl or C 1-4 alkoxy, and each A.sup.⊖ is an anion, wherein each halo is independently fluoro, chloro or bromo.
Claim 2
Dependent Claim
259 words
A compound of the formula ##STR72## wherein R is 2,7-fluoroenylene, ##STR73## wherein Z is a direct bond, straight or branched C 1-6 alkylene, --CO--, --NHCSNH--, --S--, --O--, --CH═CH--, --S--S--, --SO 2 --, --NH--, --NH--CO--, --NCH 3 --CO--, ##STR74## --XO 2 NH--, ##STR75## --NR 8 --CO--(CH 2 ) n --CO--NR 8 --, --NR 8 --CO--CH═CH--CO--NR 8 --, --NR 8 --CO--NR 8 --, --CO--NH--NH--CO--, --CH 2 --CO--NH--NH--CO--CH 2 --, --CH═CH--CO--NH--NH--CO--CH═CH--, ##STR76## --O--CO--O--, --CO--O--, --CO--CO--, --O--(CH 2 ) n --O--, ##STR77## wherein each R 8 is independently hydrogen or C 1-4 alkyl, x is halo, C 1-4 alkyl or C 1-4 alkoxy, y is halo, --NHCH 2 CH 2 OH or --N(CH 2 CH 2 OH) 2 , and n is 1, 2, 3 or 4, with the proviso that Z is meta or para to each --N═N-- linkage, Zo is a direct bond, --N═N--, --CH 2 -- or --CH 2 CH 2 --, R 5 is hydrogen, halo, C 1-4 alkyl or C 1-4 alkoxy, R 6 is halo, C 1-4 alkyl or C 1-4 alkoxy, and R 7 is hydrogen, C 1-4 alkyl or C 1-4 alkoxy, each R 1 is independently hydrogen, C 1-4 alkyl, C 2-4 hydroxyalkyl the hydroxy group of which is in other than the 1-position or --NR 3 R 4 , wherein each of R 3 and R 4 is independently n-C 1-4 alkyl, each R 2 is independently hydrogen, n-C 1-4 alkyl, n-C 1-4 -hydroxyalkyl or C 1-4 alkoxy, and each A.sup.⊖ is an anion, wherein each halo is independently fluoro, chloro or bromo.
Claim 3
Dependent Claim
13 words
A compound according to claim 1 wherein each A.sup.⊖ is a non-chromophoric anion.
Claim 4
Dependent Claim
32 words
A compound according to claim 1 wherein the two R 1 's are identical, and the two R 2 's are identical and are in the identical positions of the pyridinium rings.
Claim 5
Dependent Claim
10 words
A compound according to claim 1 wherein R is 2,7-fluorenylene.
Claim 6
Dependent Claim
10 words
A compound according to claim 1 wherein R is ##STR78##
Claim 7
Dependent Claim
72 words
A compound according to claim 5 wherein Z is a direct bond, straight or branched C 1-6 -alkylene, --CO--, --NHCSNH--, --S--, --O--, --CH═CH--, --S--S--, --SO 2 --, --NH--, --NH--CO--, --NCH 3 --CO--, ##STR79## --SO 2 NH--, ##STR80## --NR 8 --CO--(CH 2 ) n --CO--NR 8 --, --NR 8 --CO--CH═CH--CO--NR 8 --, --NR 8 --CO--NR 8 --, --CO--NH--NH--CO--, --CH 2 --CO--NH--NH--CO--CH 2 --, --CH═CH--CO--NH--NH--CO--CH═CH--, --O--CO--O--, --CO--O--, --CO--CO-- or --O--(CH 2 ) n --O--.
Claim 8
Dependent Claim
16 words
A compound according to claim 6 having the formula ##STR81## wherein each A.sup.⊖ is an anion.
Claim 9
Dependent Claim
11 words
The compound according to claim 7 wherein each A.sup.⊖ is chloride.
Claim 10
Dependent Claim
10 words
A compound according to claim 5 wherein Z is ##STR82##
Claim 11
Dependent Claim
10 words
A compound according to claim 5 wherein Z is ##STR83##
Claim 12
Dependent Claim
10 words
A compound according to claim 5 wherein Z is ##STR84##
Claim 13
Dependent Claim
10 words
A compound according to claim 1 wherein R is ##STR85##
Claim 14
Dependent Claim
21 words
A compound according to claim 12 wherein Zo is a direct bond, --CH 2 -- or --CH 2 CH 2 --.
Claim 15
Dependent Claim
10 words
A compound according to claim 12 wherein Zo is --N═N--.
Claim 16
Dependent Claim
184 words
A compound according to claim 1 having the formula ##STR86## wherein R" is ##STR87## wherein Z' is --S--, --O--, --CH═CH--, --NH--, --NH--CO--, ##STR88## --SO 2 NH--, ##STR89## --CO--NH--NH--CO--, --CH 2 --CO--NH--NH--CO--CH 2 --, --CH═CH--CO--NH--NH--CO--CH═CH--, ##STR90## --O--CO--O--, --CO--O--, --CO--CO--, --CH 2 CH 2 --, --NH--CO--NH--, ##STR91## ##STR92## --NH--CO--CH 2 CH 2 --CO--NH--, --NH--CO--(CH 2 ) 4 --CO--NH--, --NH--CO--CH═CH--CO--NH--, --NCH 3 --CO--CH 2 CH 2 --CO--NCH 3 --, --NCH 3 --CO--CH═CH--CO--NCH 3 --, --NCH 3 --CO--NCH 3 --, --O--CH 2 CH 2 --O--, ##STR93## wherein x' is hydrogen, chloro, methyl or methoxy, and y' is chloro, --NH--CH 2 CH 2 OH or --N(CH 2 CH 2 OH) 2 , Zx' is --NH--CO--, ##STR94## --NH--CO--CH 2 CH 2 --CO--NH-- or --NHCO--CH═CH--CO--NH--, Zo' is a direct bond, --CH 2 -- or --CH 2 CH 2 -- and each R 5 ' is chloro, methyl or methoxy, with the proviso that the two R 5 ''s are identical, each R 1 ' is independently hydrogen, methyl, ethyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxy-1-methylethyl or dimethylamino, each R 2 ' is independently hydrogen, methyl, methoxy or 2-hydroxyethyl, and each A.sup.⊖ is an anion.
Claim 17
Dependent Claim
32 words
A compound according to claim 15 wherein the two R 1 ''s are identical, and the two R 2 ''s are identical and are in the identical positions of the pyridinium rings.
Claim 18
Dependent Claim
26 words
A compound according to claim 15 wherein each R 1 ' is independently hydrogen or methyl, and each R 2 ' is independently hydrogen or methyl.
Claim 19
Dependent Claim
10 words
A compound according to claim 15 wherein R" is ##STR95##
Claim 20
Dependent Claim
70 words
A compound according to claim 18 wherein Z' is --S--, --O--, --CH═CH--, --NH--, --NH--CO--, ##STR96## --SO 2 NH--, ##STR97## --CO--NH--NH--CO--, --CH 2 --CO--NH--NH--CO--CH 2 --, --CH═CH--CO--NH--NH--FCO--CH═CH--, --O--CO--O--, --CO--O--, --CO--CO--, --CH 2 CH 2 --, --NH--CO--NH--, ##STR98## --NH--CO--CH 2 CH 2 --CO--NH--, --NHCO--CH═CH--CO--NH--, --NH--CO--(CH 2 ) 4 --CO--NH--, --NCH 3 --CO--CH 2 --CO--NCH 3 --, --NCH 3 --CO--CH═CH--CO--NCH 3 --, --NCH 3 --CO--NCH 3 -- or --O--CH 2 CH 2 --O--.
Claim 21
Dependent Claim
10 words
A compound according to claim 18 wherein Z' is ##STR99##
Claim 22
Dependent Claim
10 words
A compound according to claim 18 wherein Z' is ##STR100##
Claim 23
Dependent Claim
10 words
A compound according to claim 18 wherein Z' is ##STR101##
Claim 24
Dependent Claim
10 words
A compound according to claim 15 wherein R" is ##STR102##
Claim 25
Dependent Claim
10 words
A compound according to claim 15 wherein R" is ##STR103##
Claim 26
Dependent Claim
89 words
A compound according to claim 15 having the formula ##STR104## wherein R"' is ##STR105## wherein Z" is --NH--CO--, ##STR106## --CH 2 --CO--NH--NH--CO--CH 2 --, ##STR107## --CH 2 CH 2 --, ##STR108## --NH--CO--CH 2 CH 2 --CO--NH--, --NHCO--CH═CH--CO--NH--, --NH--CO--(CH 2 ) 4 --CO--NH--, --NCH 3 --CO--CH 2 CH 2 --CO--NCH 3 --, --NCH 3 --CO--CH═CH--CO--NCH 3 -- or ##STR109## each R 1 ' is independently hydrogen, methyl, ethyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxy-1-methylethyl or dimethylamino, each R 2 ' is independently hydrogen, methyl, methoxy or 2-hydroxyethyl, and each A.sup.⊖ is an anion.
Claim 27
Dependent Claim
32 words
A compound according to claim 25 wherein the two R 1 ''s are identical, and the two R 2 ''s are identical and are in the identical positions of the pyridinium rings.
Claim 28
Dependent Claim
26 words
A compound according to claim 25 wherein each R 1 ' is independently hydrogen or methyl, and each R 2 ' is independently hydrogen or methyl.
Claim 29
Dependent Claim
46 words
A compound according to claim 25 wherein Z" is --NH--CO--, ##STR110## --CH 2 --CO--NH--NH--CO--CH 2 --, --CH 2 CH 2 --, ##STR111## --NH--CO--CH 2 CH 2 --CO--NH--, --NHCO--CH═CH--CO--NH--, --NH--CO--(CH 2 ) 4 --CO--NH--, --NCH 3 --CO--CH 2 --CO--NCH 3 -- or --NCH 3 --CO--CH═CH--CO--NCH 3 --.
Claim 30
Dependent Claim
10 words
A compound according to claim 25 wherein Z" is ##STR112##
Claim 31
Dependent Claim
10 words
A compound according to claim 25 wherein Z" is ##STR113##
Claim 32
Dependent Claim
10 words
A compound according to claim 25 wherein Z" is ##STR114##
Claim 33
Dependent Claim
46 words
A compound according to claim 25 having the formula ##STR115## wherein R iv is ##STR116## wherein Z"' is --NH--CO--, ##STR117## --CH 2 CH 2 -- or ##STR118## each R 1 " and R 2 " is independently hydrogen or methyl, and each A.sup.⊖ is an anion.
Claim 34
Dependent Claim
32 words
A compound according to claim 32 wherein the two R 1 "'s are identical, and the two R 2 "'s are identical and are in the identical positions of the pyridinium rings.
Claim 35
Dependent Claim
18 words
A compound according to claim 32 wherein Z"' is --NH--CO--, ##STR119## --CH 2 CH 2 -- or ##STR120##
Claim 36
Dependent Claim
16 words
A compound according to claim 34 having the formula ##STR121## wherein each A.sup.⊖ is an anion.
Claim 37
Dependent Claim
10 words
A compound according to claim 32 wherein Z"' is ##STR122##
Claim 38
Dependent Claim
28 words
A compound according to claim 15 having the formula ##STR123## wherein Z iv is --CH 2 CH 2 --, --NH--CO--NH--, --NH--CO--CH═CH--CO--NH--, ##STR124## and each A.sup.⊖ is an anion.
Claim 39
Dependent Claim
16 words
A compound according to claim 37 having the formula ##STR125## wherein each A.sup.⊖ is an anion.
Claim 40
Dependent Claim
11 words
The compound according to claim 38 wherein each A.sup.⊖ is chloride.
Claim 41
Dependent Claim
16 words
A compound according to claim 37 having the formula ##STR126## wherein each A.sup.⊖ is an anion.
Claim 42
Dependent Claim
16 words
A compound according to claim 37 having the formula ##STR127## wherein each A.sup.⊖ is an anion.
Claim 43
Dependent Claim
14 words
A liquid dye composition comprising a solution of a compound according to claim 1.
Claim 44
Dependent Claim
11 words
A granulated dye composition comprising a compound according to claim 1.
Claim 45
Dependent Claim
30 words
A process for the production of dyed paper comprising applying to paper or incorporating into paper pulp and forming paper from said paper pulp a compound according to claim 1.
Claim 46
Dependent Claim
90 words
A compound of the formula ##STR128## wherein R q is straight chain C 2-4 alkylene, each R 1q is independently hydrogen, C 1-4 alkyl, C 2-4 hydroxyalkyl the hydroxy group of which is in other than the 1-position or --NR 4q R 5q , wherein each of R 4q and R 5q is independently n-C 1-4 alkyl, each R 2q is independently hydrogen, n-C 1-4 alkyl, n-C 1-4 -hydroxyalkyl or C 1-4 alkoxy, each R 3q is independently hydrogen or C 1-4 alkyl, and each A.sup.⊖ is a non-chromophoric anion.
Claim 47
Dependent Claim
90 words
A compound of the formula ##STR128## wherein R q is straight chain C 2-4 alkylene, each R 1q is independently hydrogen, C 1-4 alkyl, C 2-4 hydroxyalkyl the hydroxy group of which is in other than the 1-position or --NR 4q R 5q , wherein each of R 4q and R 5q is independently n-C 1-4 alkyl, each R 2q is independently hydrogen, n-C 1-4 alkyl, n-C 1-4 -hydroxyalkyl or C 1-4 alkoxy, each R 3q is independently hydrogen or C 1-4 alkyl, and each A.sup.⊖ is a non-chromophoric anion.
Claim 48
Dependent Claim
11 words
A compound according to claim 45 wherein R q is 1,2-ethylene.
Claim 49
Dependent Claim
80 words
A compound according to claim 46 wherein each R 1q is hydrogen, methyl, ethyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxy-1-methylethyl or dimethylamino, with the proviso that the two R 1q 's are identical, each R 2q is hydrogen, methyl, methoxy or 2-hydroxyethyl, with the proviso that the two R 2q 's are identical and are in the identical positions of the pyridinium rings, and each R 3q is hydrogen, methyl or ethyl, with the proviso that the two R 3q 's are identical.
Claim 50
Dependent Claim
54 words
A compound according to claim 47 wherein each R 1q is hydrogen or methyl, with the proviso that the two R 1q 's are identical, and each R 2q is hydrogen or methyl, with the proviso that the two R 2q 's are identical and are in the identical positions of the pyridinium rings.
Claim 51
Dependent Claim
18 words
A compound according to claim 48 wherein each R 1q is hydrogen, and each R 2q is hydrogen.
Claim 52
Dependent Claim
12 words
A compound according to claim 49 wherein each R 3q is hydrogen.
Claim 53
Dependent Claim
10 words
The compound according to claim 50 having the formula ##STR129##
Claim 54
Dependent Claim
10 words
The compound according to claim 46 having the formula ##STR130##
Claim 55
Dependent Claim
14 words
A liquid dye composition comprising a solution of a compound according to claim 45.
Claim 56
Dependent Claim
11 words
A granulated dye composition comprising a compound according to claim 45.
Claim 57
Dependent Claim
30 words
A process for the production of dyed paper comprising applying to paper or incorporating into paper pulp and forming paper from said paper pulp a compound according to claim 45.
Claim 58
Dependent Claim
35 words
A process for dyeing or printing a textile substrate dyeable with basic dyes comprising applying to a textile substrate dyeable with basic dyes, as a dyeing or printing agent, a compound according to claim 45.
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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) | 1994-06-10 | 1994-12-10 | 1995-06-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-06-10 | 1998-12-10 | 1999-06-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-06-10 | 2002-12-10 | 2003-06-11 | $7700.00 | Window Closed / Lapsed |