US4491481A
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Organic pigment compositions containing an azo compound with a heterocyclic substituent
Assignee: BASF Corp
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Filing: 1980-09-23
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Granted: 1985-01-01
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Expires: 2000-09-23
Abstract
Abstract A pigment composition comprising (a) an organic pigment and (b) from 0.5% to 20% by weight, based on the weight of organic pigment, of a pigment derivative having the formula: A--[N═N--B].sub.n wherein n is 1 or 2, A is an aryl or heterocyclic residue, B is an aryl or heterocyclic residue and wherein A and/or B contains a residue having the formula: ##STR1## wherein Z is a group of atoms necessary to complete a benzimidazole, pyridine, benzodiazepine, quinoline, isoquinoline or naphthimidazole residue, gives printing inks and especially paint media having improved tinctorial strength, gloss and especially improved rheological properties.
Inventors
- 👤 George H. Robertson
- 👤 David Price
- 👤 Raymond N. Birrell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:52
CPC Classifications
C; C09; C09D; C09D17/00; C09D17/003; C09B; C09B67/00; C09B67/0033; C09B67/0041
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
288 words
A pigment composition comprising: (a) an organic pigment selected from the group consisting of phthalocyanine, quinacridone, anthraquinone, and azo pigments; and (b) an azo compound of the formula A--N=N--B].sub.n wherein n is 1 or 2, A and B are radicals of either a coupling component or a diazo component, wherein the coupling component is selected from the group consisting of acetoacetyl arylamide, 1-alryl-pyrazol-5-one, β-naphthol, 3-hydroxy-2-naphthoic acid anilide, 1,3- or 1,4-bisacetoacetyl-phenylene diamine or wherein each of said acetoacetyl arylamide, 1-aryl-pyrazol-5-one, β-naphthol, 3-hydroxy-2-naphthoic acid anilide or 1,3- or 1,4-biasacetoacetyl-phenylene diamine is substituted by chloro, bromo, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate, or arylazo, and a compound of the formula ##STR11## wherein Z is a group of atoms necessary to complete a benzimidazole, pyridine, benzodiazepine, quinoline, isoquinoline or naphthimidazole group; and the diazo component is derived from an amine A(NH 2 ) n or B(NH 2 ) where A and B are selected from the group consisting of naphthyl, phenyl, diphenyl, or wherein said naphthyl, phenyl, and diphenyl are each substituted by chloro, bromo, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, nitro, carboxylic acid, sulfonic acid, alkali metal carboxylate, alkali metal sulphonate, or arylazo and a compound of the formula, ##STR12## provided where A is the coupling component, B is the diazo component, when A is the diazo component, B is the coupling component and azo compound (b) must contain at least one benzimidazole, pyridine, benzodiazepine, quinoline, isoquinoline or naphthimidazole group; wherein said azo compound is present in an amount of from 0.5% to 20% by weight, based upon the weight of said organic pigment(a).
Claim 2
Dependent Claim
288 words
A pigment composition comprising: (a) an organic pigment selected from the group consisting of phthalocyanine, quinacridone, anthraquinone, and azo pigments; and (b) an azo compound of the formula A--N=N--B].sub.n wherein n is 1 or 2, A and B are radicals of either a coupling component or a diazo component, wherein the coupling component is selected from the group consisting of acetoacetyl arylamide, 1-alryl-pyrazol-5-one, β-naphthol, 3-hydroxy-2-naphthoic acid anilide, 1,3- or 1,4-bisacetoacetyl-phenylene diamine or wherein each of said acetoacetyl arylamide, 1-aryl-pyrazol-5-one, β-naphthol, 3-hydroxy-2-naphthoic acid anilide or 1,3- or 1,4-biasacetoacetyl-phenylene diamine is substituted by chloro, bromo, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate, or arylazo, and a compound of the formula ##STR11## wherein Z is a group of atoms necessary to complete a benzimidazole, pyridine, benzodiazepine, quinoline, isoquinoline or naphthimidazole group; and the diazo component is derived from an amine A(NH 2 ) n or B(NH 2 ) where A and B are selected from the group consisting of naphthyl, phenyl, diphenyl, or wherein said naphthyl, phenyl, and diphenyl are each substituted by chloro, bromo, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, nitro, carboxylic acid, sulfonic acid, alkali metal carboxylate, alkali metal sulphonate, or arylazo and a compound of the formula, ##STR12## provided where A is the coupling component, B is the diazo component, when A is the diazo component, B is the coupling component and azo compound (b) must contain at least one benzimidazole, pyridine, benzodiazepine, quinoline, isoquinoline or naphthimidazole group; wherein said azo compound is present in an amount of from 0.5% to 20% by weight, based upon the weight of said organic pigment(a).
Claim 3
Dependent Claim
16 words
A pigment composition as claimed in claim 1 wherein the organic pigment is an azo pigment.
Claim 4
Dependent Claim
17 words
A pigment composition as claimed in claim 2 wherein the azo pigment is an arylamide azo pigment.
Claim 5
Dependent Claim
25 words
A pigment composition as claimed in claim 1 wherein A is derived from an amine A(NH 2 ) n wherein n is 1 or 2.
Claim 6
Dependent Claim
54 words
A pigment composition as claimed in claim 4 wherein A is naphthyl, phenyl, diphenyl, or wherein said naphthyl, phenyl, and diphenyl are each substituted by chloro, bromo, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate, or arylazo.
Claim 7
Dependent Claim
67 words
A pigment composition as claimed in claim 1 wherein n is 1 and A is acetoacetyl arylamide, 1-aryl-pyrazol-5-one, β-naphthol, 3-hydroxy-2-naphthoic acid anilide, or wherein each of said acetoacetyl arylamide, 1-aryl-pyrazol-5-one, β-naphthol or 3-hydroxy-2-naphthoic acid anilide is substituted by chloro, bromo, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate, or arylazo.
Claim 8
Dependent Claim
60 words
A pigment composition as claimed in claim 1 wherein n is 2 and A is 1,3- or 1,4-bisacetoacetyl-phenylene diamine, or wherein each of said 1,3- or 1,4-bisacetoacetyl-phenylene diamine is substitute by chloro, bromo, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate, or arylazo.
Claim 9
Dependent Claim
44 words
A pigment composition as claimed in claim 1 wherein A is the radical of a diazo component of the formula: ##STR13## wherein X is a hydrogen, halogen, 1-6C alkyl, 1-6C alkoxy, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate or arylazo.
Claim 10
Dependent Claim
61 words
A pigment composition as claimed in claim 1 wherein B is the radical of a coupling component of the formula ##STR14## wherein X is hydrogen, halogen, 1-6C alkyl, 1-6C alkoxy, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate or arylazo groups and Y is --CH 2 --CN, --CH 2 --COCH 3 , or --NHCOCH 2 --COCH 3 .
Claim 11
Dependent Claim
44 words
A pigment composition as claimed in claim 1 wherein A is the radical of a diazo component of the formula ##STR15## wherein X is hydrogen, halogen, 1-6C alkyl, 1-6C alkoxy, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate or arylazo group.
Claim 12
Dependent Claim
44 words
A pigment composition as claimed in claim 1 wherein B is the radical of a coupling component of the formula ##STR16## wherein X is hydrogen, halogen, 1-6C alkyl, 1-6C alkoxy, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate or arylazo group.
Claim 13
Dependent Claim
44 words
A pigment composition as claimed in claim 1 wherein B is the radical of a coupling component of the formula ##STR17## wherein X is hydrogen, halogen, 1-6C alkyl, 1-6C alkoxy, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate or arylazo group.
Claim 14
Dependent Claim
44 words
A pigment composition as claimed in claim 1 wherein B is the radical of a coupling component of the formula ##STR18## wherein X is hydrogen, halogen, 1-6C alkyl, 1-6C alkoxy, nitro, carboxylic acid, sulphonic acid, alkali metal carboxylate, alkali metal sulphonate or arylazo group.
Claim 15
Dependent Claim
12 words
A surface coating containing a pigment composition as claimed in claim 1.
Claim 16
Dependent Claim
28 words
A surface coating as claimed in claim 14 wherein the surface coating is a gravure ink, a viscous printing ink or a long or short oil alkyd paint.
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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) | 1988-01-01 | 1988-07-02 | 1989-01-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-01-01 | 1992-07-02 | 1993-01-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-01-01 | 1996-07-02 | 1997-01-01 | $7700.00 | Window Closed / Lapsed |