Patent US3472075A successfully refreshed from Google Patents.
Patent US4550158A successfully refreshed from Google Patents.
US4550158A
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Metal-free disazo compounds containing at least two basic water-solubilizing groups and having a 1-phenylpyrazole middle component radical and a 6-hydroxyprid-2-one terminal coupling component
Assignee: Sandoz AG
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Filing: 1982-08-18
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Granted: 1985-10-29
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Expires: 2002-08-18
Abstract
Abstract Metal-free azo compounds of the formula <IMAGE> wherein Ra is an aromatic group or an active methylene coupling component radical as defined in the specification, Rt is an arylazo group or a group of the formula -Y-Z, wherein Y is a direct bond or a bridging radical, and Z is a basic amino or quaternary ammonium group, <IMAGE> wherein each of the variables is as defined above or below, X is a direct bond or a bridging radical, x is hydrogen, hydroxy C1-4alkyl, C1-4alkoxy, amino or carboxy, ring B is further unsubstituted or further substituted, d is 0, 1 or 2, and n is 0 or 1, with the provisos that (i) the compounds contain an average of at least 1.3 basic water-solubilizing groups, and (ii) the compounds are free of sulfo groups, and 1:1 and 1:2 metal complexes thereof, which metal-free compounds and metal complexes are useful as dyes for leather and paper.
Inventors
- 👤 Paul Doswald
- 👤 Emil Moriconi
- 👤 Helmut Moser
- 👤 Horst Schmid
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:39
CPC Classifications
C; C09; C09B; C09B44/00; C09B44/02; C09B45/00
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
426 words
A compound of the formula ##STR181## wherein A 4 is --OH, --NH 2 , --COOH, C 1-4 alkoxy or hydrogen, R 20 is hydrogen or nitro, R 21 is hydrogen, nitro, --NH--CO--(CH 2 ) 2 --Z 2 , --CH 2 --Z 2 , --SO 2 --NH--(CH 2 ) s --Z 2 , --SO 2 NH 2 , --CO--CH 2 --Z 2 , --CO--NH--(CH 2 ) 2 --Z 2 , ##STR182## R 22 is hydrogen, nitro, --SO 2 NH 2 , --SO 2 N(R 22a ) 2 , --SO 2 --NH--(CH 2 ) s --OH, --CH 2 --Z 2 , --SO 2 --NH--(CH 2 ) s --Z 2 , --CO--NH--(CH 2 ) s --Z 2 , --NH--CO--(CH 2 ) s --Z 2 , ##STR183## wherein each R 22a is independently C 1-4 alkyl, R 23 is hydrogen or methyl, R 24 is hydrogen, C 1-4 alkyl, 2-hydroxyethyl, --(CH 2 ) p --Z 2 , benzyl, --N(R 30 ) 2 , --(CH 2 ) 3 --OCH 3 , --CH 2 --CH(CH 3 )--N(R 30 ) 2 or --CH 2 --C(CH 3 ) 2 --CH 2 --N(R 30 ) 2 , wherein each R 30 is independently hydrogen or C 1-4 alkyl, R 24a is C 1-4 alkyl, R 152 is methyl or carboxy, ##STR184## wherein Z o is --S--, --O-- or --NR 35 '--, wherein R 35 ' is hydrogen, C 1-4 alkyl or (C 1-4 -alkoxy)carbonylmethyl, and each R 127 and m are as defined below, and yo' is --OH or --NH 2 , wherein each Z 2 is independently --NH 2 , --N(R o ) 2 , --N.sup.⊕ (R o ) 3 A.sup.⊖, ##STR185## wherein each R o is independently methyl, ethyl, 2-hydroxyethyl, benzyl, acetylmethyl or benzoylmethyl, with the proviso that no nitrogen atom contains more than one member of the group consisting of benzyl, acetylmethyl and benzoylmethyl, and no nitrogen atom contains more than two 2-hydroxyethyl groups, each R 127 is independently methyl or ethyl, and m is 0, 1 or 2, each A.sup.⊖ is independently a non-chromophoric anion, each p is independently 1, 2 or 3, and each s is independently 1, 2, 3, 4, 5 or 6, with the provisos that (i) the compound contains at least two basic water-solubilizing groups, (ii) at least one of R 20 and R 21 is other than nitro, (iii) R 21 and R 22 are different unless both are hydrogen, (iv) R 20 is hydrogen when both R 21 and R 22 are hydrogen, and (v) at least one of R 20 -R 23 is hydrogen.
Claim 2
Dependent Claim
426 words
A compound of the formula ##STR181## wherein A 4 is --OH, --NH 2 , --COOH, C 1-4 alkoxy or hydrogen, R 20 is hydrogen or nitro, R 21 is hydrogen, nitro, --NH--CO--(CH 2 ) 2 --Z 2 , --CH 2 --Z 2 , --SO 2 --NH--(CH 2 ) s --Z 2 , --SO 2 NH 2 , --CO--CH 2 --Z 2 , --CO--NH--(CH 2 ) 2 --Z 2 , ##STR182## R 22 is hydrogen, nitro, --SO 2 NH 2 , --SO 2 N(R 22a ) 2 , --SO 2 --NH--(CH 2 ) s --OH, --CH 2 --Z 2 , --SO 2 --NH--(CH 2 ) s --Z 2 , --CO--NH--(CH 2 ) s --Z 2 , --NH--CO--(CH 2 ) s --Z 2 , ##STR183## wherein each R 22a is independently C 1-4 alkyl, R 23 is hydrogen or methyl, R 24 is hydrogen, C 1-4 alkyl, 2-hydroxyethyl, --(CH 2 ) p --Z 2 , benzyl, --N(R 30 ) 2 , --(CH 2 ) 3 --OCH 3 , --CH 2 --CH(CH 3 )--N(R 30 ) 2 or --CH 2 --C(CH 3 ) 2 --CH 2 --N(R 30 ) 2 , wherein each R 30 is independently hydrogen or C 1-4 alkyl, R 24a is C 1-4 alkyl, R 152 is methyl or carboxy, ##STR184## wherein Z o is --S--, --O-- or --NR 35 '--, wherein R 35 ' is hydrogen, C 1-4 alkyl or (C 1-4 -alkoxy)carbonylmethyl, and each R 127 and m are as defined below, and yo' is --OH or --NH 2 , wherein each Z 2 is independently --NH 2 , --N(R o ) 2 , --N.sup.⊕ (R o ) 3 A.sup.⊖, ##STR185## wherein each R o is independently methyl, ethyl, 2-hydroxyethyl, benzyl, acetylmethyl or benzoylmethyl, with the proviso that no nitrogen atom contains more than one member of the group consisting of benzyl, acetylmethyl and benzoylmethyl, and no nitrogen atom contains more than two 2-hydroxyethyl groups, each R 127 is independently methyl or ethyl, and m is 0, 1 or 2, each A.sup.⊖ is independently a non-chromophoric anion, each p is independently 1, 2 or 3, and each s is independently 1, 2, 3, 4, 5 or 6, with the provisos that (i) the compound contains at least two basic water-solubilizing groups, (ii) at least one of R 20 and R 21 is other than nitro, (iii) R 21 and R 22 are different unless both are hydrogen, (iv) R 20 is hydrogen when both R 21 and R 22 are hydrogen, and (v) at least one of R 20 -R 23 is hydrogen.
Claim 3
Dependent Claim
23 words
A compound according to claim 1 wherein one of R 21 and R 22 is hydrogen, and the other is other than hydrogen.
Claim 4
Dependent Claim
32 words
A compound according to claim 1 wherein A 4 is --OH, --NH 2 , --COOH or C 1-4 alkoxy, with the proviso that the compound contains 2 to 4 basic water-solubilizing groups.
Claim 5
Dependent Claim
296 words
A compound according to claim 1 having the formula ##STR186## wherein D 10 is ##STR187## wherein R 23 is hydrogen or methyl, R 33 ' is hydroxy, methoxy, ethoxy or carboxy, R 34 is hydrogen, nitro, --SO 2 NH 2 or --CH 2 --Z 2 , and R 35 is hydrogen, nitro, --SO 2 NH--(CH 2 ) 2 --OH, --SO 2 NH 2 , --SO 2 NH--(CH 2 ) 3 --N(CH 3 ) 2 or ##STR188## R 24 ' is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, 2-hydroxyethyl, benzyl, dimethylamino, --(CH 2 ) m' --Z 2 , ##STR189## or --CH 2 --C(CH 3 ) 2 --CH 2 --N(CH 3 ) 2 , and d' is 0 or 1, wherein each Z 2 is independently --NH 2 , --N(R o ) 2 , --N.sup.⊕ (R o ) 3 A.sup.⊖, ##STR190## wherein each R o is independently methyl, ethyl, 2-hydroxyethyl, benzyl, acetylmethyl or benzoylmethyl, with the proviso that no nitrogen atom contains more than one member of the group consisting of benzyl, acetylmethyl and benzoylmethyl, and no nitrogen atom contains more than two 2-hydroxyethyl groups, each R 127 is independently methyl or ethyl, m is 0, 1 or 2, and p is 1, 2 or 3, each A.sup.⊖ is independently a non-chromophoric anion, and each m' is independently 2 or 3, with the provisos that (i) R 34 and R 35 are different or R 34 and R 35 are both hydrogen, (ii) when R 35 is 2,4--(bis(3'-diethylamino)propylamino)-1,3,5-triazin-6-ylamino or --SO 2 NH--(CH 2 ) 3 --N(CH 3 ) 2 , at least one of R 23 and R 34 is other than hydrogen, (iii) the --N═N-- radical attached to ring E is in the 3- or 4-position, and (iv) the compound contains at least two basic water-solubilizing groups.
Claim 6
Dependent Claim
36 words
A compound according to claim 4 wherein D 10 is ##STR191## wherein one of R 34 and R 35 is hydrogen, and the other is other than hydrogen, and each p is independently 2 or 3.
Claim 7
Dependent Claim
301 words
A compound according to claim 4 having the formula ##STR192## wherein D 10 ' is ##STR193## wherein R 23 is hydrogen or methyl, R 34 is hydrogen, nitro, --SO 2 NH 2 or --CH 2 --Z 2 , wherein Z 2 is --NH 2 , --N(R o ) 2 , --N.sup.⊕ (R o ) 3 A.sup.⊖, ##STR194## wherein each R o is independently methyl, ethyl, 2-hydroxyethyl, benzyl, acetylmethyl or benzoylmethyl, with the provisos that no nitrogen atom contains more than one member of the group consisting of benzyl, acetylmethyl and benzoylmethyl, and no nitrogen atom contains more than two 2-hydroxyethyl groups, each R 127 is independently methyl or ethyl, and m is 0, 1 or 2, and R 35 is hydrogen, nitro, --SO 2 NH--(CH 2 ) 2 --OH, --SO 2 NH 2 '--SO 2 NH--(CH 2 ) 3 --N(CH 3 ) 2 or ##STR195## R 24 " is hydrogen, methyl, ethyl, 2-hydroxyethyl or --(CH 2 ) m' --Z 3 , wherein each Z 3 is independently --N(CH 3 ) 2 , --N(C 2 H 5 ) 2 , --N.sup.⊕ (CH 3 ) 3 A.sup.⊖, --N.sup.⊕ (C 2 H 5 ) 3 A.sup.⊖, ##STR196## each A.sup.⊖ is independently a non-chromophoric anion, each d' is independently 0 or 1, each m' is independently 2 or 3, and each p is independently 1, 2 or 3, with the provisos that (i) R 34 and R 35 are different or R 34 and R 35 are both hydrogen, (ii) when R 35 is 2,4-(bis(3'-diethylamino)propylamino)-1,3,5-triazin-6-ylamino or --SO 2 NH--(CH 2 ) 3 --N(CH 3 ) 2 , at least one of R 23 and R 34 is other than hydrogen, (iii) the --N═N-- radical attached to ring E is in the 3- or 4-position, and (iv) the compound contains at least two basic water-solubilizing groups.
Claim 8
Dependent Claim
37 words
A compound according to claim 6 wherein D 10 ' is ##STR197## wherein one of R 34 and R 35 is hydrogen, and the other is other than hydrogen, and each p is independently 2 or 3.
Claim 9
Dependent Claim
179 words
A compound according to claim 6 having the formula ##STR198## wherein D 10 " is ##STR199## wherein each Z 5 is independently --N(CH 3 ) 2 , --N(C 2 H 5 ) 2 , ##STR200## each m' is independently 2 or 3, and R 23 , R 34 and R 35 are as defined in claim 6, and R 24 "' is hydrogen, 2-hydroxyethyl, --(CH 2 ) 3 --N(CH 3 ) 2 , --(CH 2 ) 3 --N(C 2 H 5 ) 2 or --(CH 2 ) 3 --N.sup.⊕ (CH 3 ) 3 A.sup.⊖, wherein each A.sup.⊖ is independently a non-chromophoric anion, with the provisos that (i) R 34 and R 35 are different or R 34 and R 35 are both hydrogen, (ii) when R 35 is 2,4-(bis(3'-diethylamino)propylamino)-1,3,5-triazin-6-ylamino or --SO 2 NH--(CH 2 ) 3 --N(CH 3 ) 2 , at least one of R 23 and R 34 is other than hydrogen, (iii) the --N═N-- radical attached to ring E is in the 3- or 4-position, and (iv) the compound contains at least two basic water-solubilizing groups.
Claim 10
Dependent Claim
29 words
A compound according to claim 8 wherein D 10 " is ##STR201## wherein one of R 34 and R 35 is hydrogen, and the other is other than hydrogen.
Claim 11
Dependent Claim
36 words
A compound according to claim 8 wherein D 10 " is 2-hydroxy-5-nitrophenyl, R 24 "' is --(CH 2 ) 3 --N(CH 3 ) 2 , and the --N═N-- radical is in the 4-position of ring E.
Claim 12
Dependent Claim
10 words
The compound according to claim 10 wherein A.sup.⊖ is chloride.
Claim 13
Dependent Claim
36 words
A compound according to claim 8 wherein D 10 " is 2-hydroxy-4-nitrophenyl, R 24 "' is --(CH 2 ) 3 --N(CH 3 ) 2 , and the --N═N-- radical is in the 4-position of ring E.
Claim 14
Dependent Claim
10 words
The compound according to claim 12 wherein A.sup.⊖ is chloride.
Claim 15
Dependent Claim
36 words
A compound according to claim 8 wherein D 10 " is 2-hydroxy-5-nitrophenyl, R 24 "' is --(CH 2 ) 3 --N(CH 3 ) 2 , and the --N═N-- radical is in the 3-position of ring E.
Claim 16
Dependent Claim
10 words
The compound according to claim 14 wherein A.sup.⊖ is chloride.
Claim 17
Dependent Claim
36 words
A compound according to claim 8 wherein D 10 " is 2-hydroxy-5-sulfamoylphenyl, R 24 "' is --(CH 2 ) 3 --N(CH 3 ) 2 , and the --N═N-- radical is in the 3-position of ring E.
Claim 18
Dependent Claim
10 words
The compound according to claim 16 wherein A.sup.⊖ is chloride.
Claim 19
Dependent Claim
36 words
A compound according to claim 8 wherein D 10 " is 2-hydroxy-4-nitrophenyl, R 24 "' is --(CH 2 ) 3 --N(CH 3 ) 2 , and the --N═N-- radical is in the 3-position of ring E.
Claim 20
Dependent Claim
10 words
The compound according to claim 18 wherein A.sup.⊖ is chloride.
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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) | 1988-10-28 | 1989-04-29 | 1989-10-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-28 | 1993-04-29 | 1993-10-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-28 | 1997-04-29 | 1997-10-29 | $7700.00 | Window Closed / Lapsed |