US4123428A
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Metallized polyazo dyes derived from a coupling component obtained by acidic condensation of formaldehyde with at least one phenolic compound
Assignee: Sandoz AG
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Filing: 1976-08-25
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Granted: 1978-10-31
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Expires: 1996-08-25
Abstract
Abstract Metal complex polyazo dyes having, as a coupling component radical, the radical of a coupling component K, being the product of the condensation, under acidic conditions, of the formaldehyde with a compound or mixture of compounds of formula (a), <IMAGE> (a) AND/OR A COMPOUND OR MIXTURE OF COMPOUNDS OF FORMULA (B), <IMAGE> (b) WHEREIN EACH R1 , R2, R3 and R4 is independently is hydrogen, halogen, hydroxy or optionally substituted alkyl or alkoxy, and M is hydrogen or a non-chromophoric cation, THE MOL RATIO OF FORMALDEHYDE TO THE OTHER COMPOUND(S) (A) AND/OR (B) BEING AT LEAST 0.6:1 AND AT LEAST 50 MOL % OF THE OTHER COMPOUND(S) (A) AND/OR (B) CONTAINING A -COOM group, and, as diazo or bisdiazo component radical, a radical D- or -D- where D contains at least one metallized azo group, their production and their use for the dyeing of anionic dyeable substrates, particularly leather. The dyes have good levelling capacity and the obtained dyeings possess notable fastness to light.
Inventors
- 👤 Herbert Holliger
- 👤 Heinz Wicki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 04:09
CPC Classifications
C; C09; C09B; C09B45/00; D; D06; D06P; D06P3/00; D06P3/02; D06P3/04; D06P3/32; D06P3/3206; D06P3/3226; D06P3/3233
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
214 words
A metal complex polyazo dye having a diazo component radical D- or a bisdiazo component radical --D-- and, as a coupling component radical, the radical of a coupling component K, wherein D-- is a diazo component radical having at least one metallized azo group, --D-- is a bisdiazo component radical having at least one metallized azo group, and K is the product of the condensation, under acidic conditions, of formaldehyde with (i) a compound of the formula ##STR17## or a mixture of such compounds, (ii) a compound of the formula ##STR18## or a mixture of such compounds, or (iii) a compound of the formula ##STR19## or a mixture of such compounds, and a compound of the formula ##STR20## or a mixture of such compounds, wherein each of R 1 , r 2 , r 3 and R 4 is independently hydrogen, halo, hydroxy, alkyl, substituted alkyl, alkoxy or substituted alkoxy, and M is hydrogen or a non-chromophoric cation, with the provisos that the mol ratio of formaldehyde to the compound or mixture of compounds of (i), (ii) or (iii) is at least 0.6:1 and that at least 50 mol % of the compounds or mixture of compounds of (i), (ii) or (iii) contains a --COOM group, wherein M is hydrogen or a non-chromophoric cation.
Claim 2
Dependent Claim
214 words
A metal complex polyazo dye having a diazo component radical D- or a bisdiazo component radical --D-- and, as a coupling component radical, the radical of a coupling component K, wherein D-- is a diazo component radical having at least one metallized azo group, --D-- is a bisdiazo component radical having at least one metallized azo group, and K is the product of the condensation, under acidic conditions, of formaldehyde with (i) a compound of the formula ##STR17## or a mixture of such compounds, (ii) a compound of the formula ##STR18## or a mixture of such compounds, or (iii) a compound of the formula ##STR19## or a mixture of such compounds, and a compound of the formula ##STR20## or a mixture of such compounds, wherein each of R 1 , r 2 , r 3 and R 4 is independently hydrogen, halo, hydroxy, alkyl, substituted alkyl, alkoxy or substituted alkoxy, and M is hydrogen or a non-chromophoric cation, with the provisos that the mol ratio of formaldehyde to the compound or mixture of compounds of (i), (ii) or (iii) is at least 0.6:1 and that at least 50 mol % of the compounds or mixture of compounds of (i), (ii) or (iii) contains a --COOM group, wherein M is hydrogen or a non-chromophoric cation.
Claim 3
Dependent Claim
97 words
A dye according to claim 1 wherein each of R 1 , r 2 , r 3 and R 4 is independently hydrogen; fluoro; chloro; bromo; iodo; hydroxy; C 1-4 alkyl; C 1-4 alkyl substituted by fluoro, chloro, bromo, iodo, --COOM, cyano, hydroxy, C 1-4 alkoxy or C 2-4 hydroxyalkoxy; C 1-4 alkoxy or C 1-4 alkoxy substituted by fluoro, chloro, bromo, iodo, --COOM, cyano, hydroxy, C 1-4 alkoxy or C 2-4 hydroxyalkoxy, with the proviso that any C 1-4 alkoxy substituted by hydroxy, C 1-4 alkoxy or C 2-4 hydroxyalkoxy has 2 to 4 carbon atoms.
Claim 4
Dependent Claim
38 words
A dye according to claim 2 wherein each of R 1 , r 2 and R 4 is independently hydrogen, methyl, methoxy, hydroxy or chloro, and R 3 is hydrogen, methyl, methoxy, hydroxy, chloro or --O--CH 2 --COOM.
Claim 5
Dependent Claim
18 words
A dye according to claim 3 wherein at least one of R 1 and R 2 is hydrogen.
Claim 6
Dependent Claim
88 words
A dye according to claim 4 wherein K is the product of the condensation, under acidic conditions, or formaldehyde with (i) a compound of the formula ##STR21## (ii) a mixture of a compound of the formula ##STR22## with resorcinol or a cresol, wherein at least 80 mol % of the mixture is a compound of the formula ##STR23## wherein M is hydrogen or a non-chromophoric cation, with the proviso that the mol ratio of formaldehyde of the compound or mixture of compounds of (i) or (ii) is 0.6-0.95:1.
Claim 7
Dependent Claim
52 words
A dye according to claim 5 wherein K is the product of the condensation, under acidic conditions, of formaldehyde with a compound of the formula ##STR24## wherein M is hydrogen or a non-chromophoric cation, with the proviso that the mol ratio of formaldehyde to the compound of the formula ##STR25## is 0.6-0.95:1.
Claim 8
Dependent Claim
130 words
A dye according to claim 1 wherein D is a diazo component radical having at least one metallized azo group and at least one --SO 3 M group, with the proviso that the number of --SO 3 M groups that it contains is equal to or greater than the number of azo groups and equal to or less than the number of aromatic carbocyclic rings that it contains, and --D-- is a bisdiazo component radical having at least one metallized azo group and at least one --SO 3 M group, with the proviso that the number of --SO 3 M groups that it contains is equal to or greater than the number of azo groups and equal to or less than the number of aromatic carbocyclic rings that it contains.
Claim 9
Dependent Claim
193 words
A dye according to claim 1 having a diazo component radical D'-, wherein D'-- is A--N═N--B--N'N.sub.p (C--N═N.sub.q E--N═N--, wherein A is the radical of a diazo component or a coupling component, each of B and C is independently the radical of a bisdiazo component, an at least twice couplable coupling component or a coupling/diazo component, E is the radical of a bisdiazo component or a coupling/diazo component, with the provisos that B is the radical of the bisdiazo component or a coupling/diazo component when A is the radical of a coupling component and is the radical of an at least twice couplable coupling component or a coupling/diazo component when A is the radical of a diazo component and C is the radical of a bisdiazo component or a coupling/diazo component when E is the radical of a coupling/diazo component and is the radical of an at least twice couplable coupling component or a coupling/diazo component when E is the radical of a bisdiazo component, and each of p and q is independently 0 or 1, with the proviso that D' contains 2 to 5 azo groups at least one of which is metallized.
Claim 10
Dependent Claim
53 words
A dye according to claim 8 wherein each of R 1 , r 2 and R 4 is independently hydrogen, methyl, methoxy, hydroxy or chloro, with the proviso that at least one of R 1 and R 2 is hydrogen, and R 3 is hydrogen, methyl, methoxy, hydroxy, chloro or --O--CH 2 --COOM.
Claim 11
Dependent Claim
88 words
A dye according to claim 9 wherein K is the product of the condensation, under acid conditions, of formaldehyde and (i) a compound of the formula ##STR26## (ii) a mixture of a compound of the formula ##STR27## with resorcinol or a cresol, wherein at least 80 mol % of the mixture is a compound of the formula ##STR28## wherein M is hydrogen or a non-chromophoric cation, with the proviso that the mol ratio of formaldehyde to the compound or mixture of compounds of (i) or (ii) is 0.6-0.95:1.
Claim 12
Dependent Claim
15 words
A dye according to claim 9 wherein A is the radical of a diazo component.
Claim 13
Dependent Claim
130 words
A dye according to claim 11 wherein A is ##STR29## wherein R 5 is hydrogen, hydroxy or --SO 3 M, R 6 is hydrogen or nitro, R 7 is hydrogen, hydroxy, C 1-4 alkyl, C 1-4 alkoxy, --COOM or chloro, R 8 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, --COOM, chloro, --SO 3 M, nitro, formamido, (C 1-4 alkyl)carbonylamino, benzamido, phenylsulfonylamino, tolylsulfonylamino or ##STR30## wherein each of R 10 and R 11 is independently hydrogen, nitro or --SO 3 M, and R 12 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, chloro or --COOM, R 9 is hydrogen, C 1-4 alkyl, chloro, --SO 3 M, sulfamoyl or nitro, h is 0 or 1, and k is 0 or 1, wherein each M is independently hydrogen or a non-chromophonic cation.
Claim 14
Dependent Claim
89 words
A dye according to claim 12 wherein R 8 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, --COOM, chloro, --SO 3 M, nitro, formamido, acetamido, phenylsulfonylamino, tolylsulfonylamino or ##STR31## wherein each of R 10 and R 11 is independently hydrogen, nitro or --SO 3 M, and R 12 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, chloro or --COOM, and the sum of h and k is 0 or 1 when R 5 is --SO 3 M and is 1 or 2 when R 5 is hydrogen or hydroxy.
Claim 15
Dependent Claim
56 words
A dye according to claim 13 wherein R 8 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, --COOM, chloro, --SO 3 M, nitro, formamido, acetamido ##STR32## wherein each of R 10 and R 11 is independently hydrogen, nitro or --SO 3 M, and R 12 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, chloro or --COOM.
Claim 16
Dependent Claim
21 words
A dye according to claim 12 wherein each of B, C and E is independently the radical of a coupling/diazo component.
Claim 17
Dependent Claim
194 words
A dye according to claim 15 wherein each of B, c and E is independently ##STR33## or the radical of a coupling/diazo component of the formula ##STR34## wherein R 13a is hydrogen, hydroxy or ##STR35## wherein R 14 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy or chloro, R 15 is --NH 2 , acylamino, --NH--CH 2 --SO 3 M or ##STR36## wherein each of R 10 and R 11 is independently hydrogen, nitro or --SO 3 M, and R 12 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, chloro or --COOM, R 16 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, hydroxy, chloro, --NH 2 or --COOM, R 17 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, or --SO 3 M, R 18 is C 1-4 alkyl, --COOM, --COOR 21 or --COR 21 , wherein R 21 is C 1-4 alkyl or phenyl, R 19 is hydroxy or --NH 2 , R 20 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, chloro or --SO 3 M, and m is 1 or 2, with the proviso that in any radical of the formula ##STR37## the --NH 2 group is ortho to an azo group.
Claim 18
Dependent Claim
21 words
A dye according to claim 16 wherein R 15 is --NH 2 , acetamido, --NH--CH 2 --SO 3 M or ##STR38##
Claim 19
Dependent Claim
137 words
A dye according to claim 17 wherein each of B, c and E is independently ##STR39## or the radical of a coupling/diazo component of the formula ##STR40## wherein R 13 ' is hydrogen, hydroxy, phenylamino or tolylamino, R 15 ' is --NH 2 , acetamido, --NH--CH 2 --SO 3 M or ##STR41## wherein each of R 10 and R 11 is independently hydrogen, nitro or --SO 3 M, and R 12 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, chloro or --COOM, R 16 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, hydroxy, chloro, --NH 2 or --COOM, R 17 is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, or --SO 3 M, R 18 ' is methyl, R 19 ' is hydroxy, R 20 ' is hydrogen or --SO 3 M, and m is 1 or 2.
Claim 20
Dependent Claim
27 words
A dye according to claim 16 wherein each of B, c and E is independently ##STR42## or the radical of a coupling/diazo component of the formula ##STR43##
Claim 21
Dependent Claim
34 words
A dye according to claim 16 wherein one of B, c and E is ##STR44## and each of the others is independently ##STR45## or the radical of a coupling/diazo component of the formula ##STR46##
Claim 22
Dependent Claim
97 words
A dye according to claim 16 wherein each of R 1 , r 2 , r 3 and R 4 is independently hydrogen; fluoro; chloro; bromo; iodo; hydroxy; C 1-4 alkyl; C 1-4 alkyl substituted by fluoro, chloro, bromo, iodo, --COOM, cyano, hydroxy, C 1-4 alkoxy or C 2-4 hydroxyalkoxy; C 1-4 alkoxy or C 1-4 alkoxy substituted by fluoro, chloro, bromo, iodo, --COOM, cyano, hydroxy, C 1-4 alkoxy or C 2-4 hydroxyalkoxy, with the proviso that any C 1-4 alkoxy substituted by hydroxy, C 1-4 alkoxy or C 2-4 hydroxyalkoxy has 2 to 4 carbon atoms.
Claim 23
Dependent Claim
53 words
A dye according to claim 21 wherein each of R 1 , r 2 and R 4 is independently hydrogen, methyl, methoxy, hydroxy or chloro, with the proviso that at least one of R 1 and R 2 is hydrogen, and R 3 is hydrogen, methyl, methoxy, hydroxy, chloro or --O--CH 2 --COOM.
Claim 24
Dependent Claim
89 words
A dye according to claim 22 wherein K is the product of the condensation, under acid conditions, of formaldehyde and (i) a compound of the formula ##STR47## or (ii) a mixture of a compound of the formula ##STR48## with resorcinol or a cresol, wherein at least 80 mol % of the mixture is a compound of the formula ##STR49## wherein M is hydrogen or a non-chromophoric cation, with the proviso that the mol ratio of formaldehye to the compound or mixture of compounds of (i) or (ii) is 0.6-0.95:1.
Claim 25
Dependent Claim
16 words
A dye according to claim 23 wherein at least one of p and q is 0.
Claim 26
Dependent Claim
14 words
A dye according to claim 24 wherein p is 0, and q is 0.
Claim 27
Dependent Claim
28 words
A dye according to claim 23 wherein each of B, c and E is independently ##STR50## or the radical of a coupling/diazo component of the formula ##STR51## 1
References Cited (Backward Citations)
FR1503833A
Cited
US3759892A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-30 | 1982-05-01 | 1982-10-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-30 | 1986-05-01 | 1986-10-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-30 | 1990-05-01 | 1990-10-31 | $7700.00 | Window Closed / Lapsed |