WO1996025464B1 - Pigment compositions - Google Patents
Pigment compositionsInfo
- Publication number
- WO1996025464B1 WO1996025464B1 PCT/US1996/001240 US9601240W WO9625464B1 WO 1996025464 B1 WO1996025464 B1 WO 1996025464B1 US 9601240 W US9601240 W US 9601240W WO 9625464 B1 WO9625464 B1 WO 9625464B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- sulfonic acid
- carboxylic acid
- composition
- acid ester
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 33
- 239000000049 pigment Substances 0.000 title claims abstract 4
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims abstract 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 12
- 150000003459 sulfonic acid esters Chemical group 0.000 claims abstract 12
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract 11
- 150000003839 salts Chemical class 0.000 claims abstract 11
- 239000011780 sodium chloride Substances 0.000 claims abstract 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims abstract 8
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 1,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims abstract 6
- 239000003973 paint Substances 0.000 claims abstract 5
- 239000002253 acid Substances 0.000 claims abstract 4
- 150000004982 aromatic amines Chemical class 0.000 claims abstract 4
- 230000001808 coupling Effects 0.000 claims abstract 4
- 238000010168 coupling process Methods 0.000 claims abstract 4
- 238000005859 coupling reaction Methods 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 239000000987 azo dye Substances 0.000 claims abstract 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract 2
- 125000000271 carboxylic acid salt group Chemical group 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 3
- 150000001342 alkaline earth metals Chemical group 0.000 claims 3
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 3
- 229910052748 manganese Inorganic materials 0.000 claims 3
- 239000011572 manganese Substances 0.000 claims 3
- 229910052759 nickel Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- -1 cyclic aromatic amines Chemical class 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract 2
Abstract
Disclosed are compositions comprising one or more compounds characterized by formula (1) wherein Ar is an aromatic moiety having at least one substituent which is an acid group or salt thereof; X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; and a is 1, 2 or 3. Also disclosed is a process for preparing azo dyes which comprises coupling (i) at least one diazonium component of one or more aromatic amines containing at least one sulfonic acid group or carboxylic acid group, or salts thereof; with (ii) at least one coupling component represented by formula (2) wherein X, Y and a are as defined above. The dye compositions prepared by this process and the azo pigments derived from such dyes are also disclosed. Paint, ink and plastic compositions containing the foregoing pigments compositions are disclosed.
Claims
27
AMENDED CLAIMS
[received by the International Bureau on 20 August 1996 (20.08.96); original claims 1-26 replaced by amended claims 1-26 (5 pages)]
1. A composition comprising one or more compounds of by the formula:
wherein X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide, or nitro group; a is 1, 2 or 3; and Ar is an aromatic moiety having a substituent acid group or salt thereof, provided that when Ar is monocyclic it is of the formula:
wherein each Z is independently a -COOH or -S03H group or. salts of such groups; m is 1 or 2? each R is independently a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic amide, imidazolone, sulfonic acid amide or nitro group; and n is 0, 1 or 2. 2. A composition according to claim 1 wherein X is a lower alkyl group.
3. A composition according to claim 1 wherein Ar is of
the formula:
wherein R is a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, sulfonic acid amide or nitro group; and Z is a -COOH or -S03H group, or salts thereof.
4. A composition according to claim 1 wherein X and Y are lower alkyl groups and a equals 1.
5. A composition according to claim 4 wherein X and Y are methyl groups.
6. A composition according to claim 1 wherein n equals 1; Z is a -S03H group or salt thereof; and m equals 1.
7. A composition according to claim 1 wherein said acid salt is an alkali metal or ammonium salt. 8. A composition according to claim 1 wherein said acid salt is an alkaline earth metal, manganese, nickel or zinc salt.
9. A composition according to claim 1 wherein Ar is of the formula:
wherein R is a halogen or lower alkyl group.
10. An azo pigment composition comprising one or more
29
compounds of the formula:
wherein X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; a equals 1, 2 or 3; and Ar is an aromatic moeity having as a substituent a divalent metal salt of a carboxylic acid or sulfonic acid group, provided that when Ar is monocyclic it is characterized by the formula:
wherein each Z is independently a salt of a -COOH or -S03H group; m is 1 or 2 ; each R is independently a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; and n is 0, 1 or 2.
11. A composition according to claim 10 wherein Z is a sulfonic acid salt of a divalent metal selected from the group consisting of alkaline earth metals, manganese, nickel and zinc.
12. A composition according to claim 10 wherein X and
30
Y are each lower alkyl groups and a equals 1.
13. A composition according to claim 12 wherein X and
Y are methyl groups .
14. A composition according to claim 10 wherein n equals 1; R is a methyl, or chloro group.
15. A process for preparing an azo dye which comprises coupling (i) at least one diazonium component of one or more aromatic amines containing at least one sulfonic acid group or carboxylic acid group, or salts of such groups wherein the aromatic amines are selected from the group consisting of fused cyclic aromatic amines or aromatic amines of the formula:
wherein each R is independently a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; n is equal to 0, 1 or 2; each Z is independently a -COOH or -S03H group, or salts of such groups; and m is equal to 1 or 2; with (ii) at least one coupling component of the formula:
wherein X is a hydrocarbyl, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide or sulfonic acid amide group; each Y is independently a hydrocarbyl, halogen,
31
hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; and a equals 1, 2 or 3.
16. A process according to claim 15 wherein X and Y are lower alkyl groups and a equals 1.
17. A process according to claim 15 wherein X and Y are methyl groups, a equals 1; R is a methyl or chloro group; n equals 1; Z is a -S03H group or salt thereof and m equals 1. 18. A process wherein the azo dye prepared according to claim 15 is metallized with one or more of alkaline earth metals, manganese, nickel or zinc.
19. A composition prepared according to the process of claim 15. 20. A composition prepared according to the process of claim 18.
21. A paint composition comprising a major amount of a paint vehicle and a minor amount of the composition of claim
10. 22. A paint composition comprising a major amount of a paint vehicle and a minor amount of the composition of claim
18.
23. An ink composition comprising a major amount of ink vehicle and a minor amount of the composition of claim 10.
24. An ink composition comprising a major amount of ink vehicle and a minor amount of the composition of claim 18.
25. A plastic composition comprising a major amount of a plastic material and a minor amount of the composition of claim 10.
26. A plastic composition comprising a major amount of a plastic material and a minor amount of the composition of claim 18.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU48609/96A AU4860996A (en) | 1995-02-13 | 1996-01-31 | Pigment compositions |
| CA002212460A CA2212460C (en) | 1995-02-13 | 1996-01-31 | Pigment compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/387,994 US5746821A (en) | 1995-02-13 | 1995-02-13 | Pigment compositions |
| US08/387,994 | 1995-02-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996025464A1 WO1996025464A1 (en) | 1996-08-22 |
| WO1996025464B1 true WO1996025464B1 (en) | 1996-10-10 |
Family
ID=23532183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/001240 WO1996025464A1 (en) | 1995-02-13 | 1996-01-31 | Pigment compositions |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US5746821A (en) |
| AU (1) | AU4860996A (en) |
| WO (1) | WO1996025464A1 (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5669967A (en) * | 1996-05-30 | 1997-09-23 | Engelhard Corporation | Pigment compositions |
| GB9623231D0 (en) | 1996-11-07 | 1997-01-08 | Clariant Int Ltd | Improvements in or relating to organic compounds |
| US5997628A (en) * | 1998-06-08 | 1999-12-07 | Engelhard Corporation | Heat stable laked monoazo pigment compositions |
| US6235100B1 (en) | 1999-06-24 | 2001-05-22 | Engelhard Corporation | Metallized azo yellow pigments |
| US6294012B1 (en) | 1999-11-15 | 2001-09-25 | Engelhard Corporation | High strength monoazo yellow pigment |
| CY2010012I2 (en) * | 2000-05-25 | 2020-05-29 | Novartis Ag | THROMBOPOIETIN MIMETICS |
| US20110212054A1 (en) * | 2000-05-25 | 2011-09-01 | Glaxosmithkline Llc. | Thrombopoietin mimetics |
| US6375733B1 (en) | 2000-08-28 | 2002-04-23 | Engelhard Corporation | Heat stable monoazo magenta pigment compositions |
| GB0106345D0 (en) * | 2001-03-14 | 2001-05-02 | Avecia Ltd | Compounds compositions and processes |
| GB0106343D0 (en) * | 2001-03-14 | 2001-05-02 | Avecia Ltd | Compounds compositions and processes |
| AR040083A1 (en) | 2002-05-22 | 2005-03-16 | Smithkline Beecham Corp | BIS- (MONOETHANOLAMINE) ACID COMPOUND 3 '- [(2Z) - [1- (3,4-DIMETHYLPHENYL) -1,5-DIHIDRO-3-METHYL-5-OXO-4H-PIRAZOL-4-ILIDEN] HYDRAZINE ] -2'-HYDROXI- [1,1'-BIFENIL] -3-CARBOXILICO, PROCEDURE TO PREPARE IT, PHARMACEUTICAL COMPOSITION THAT INCLUDES IT, PROCEDURE TO PREPARE SUCH FARMAC COMPOSITION |
| WO2005018931A1 (en) | 2003-08-18 | 2005-03-03 | Engelhard Corporation | Solvent stable tinted iridescent film |
| TW200526638A (en) * | 2003-10-22 | 2005-08-16 | Smithkline Beecham Corp | 2-(3,4-dimethylphenyl)-4-{[2-hydroxy-3'-(1H-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one choline |
| US20070022907A1 (en) * | 2004-11-23 | 2007-02-01 | Basf Catalysts Llc | Colored Masterbatch Precursor |
| DE102007008218A1 (en) * | 2007-02-20 | 2008-08-21 | Clariant International Ltd. | Pigment composition based on C.I. Pigment Yellow 191 |
| ECSP077628A (en) * | 2007-05-03 | 2008-12-30 | Smithkline Beechman Corp | NEW PHARMACEUTICAL COMPOSITION |
| CN101376748B (en) * | 2007-08-27 | 2011-09-14 | 明德国际仓储贸易(上海)有限公司 | Yellow dye compound and ink composition thereof |
| CN101503576A (en) * | 2008-02-08 | 2009-08-12 | 吴江桃源染料厂 | Ecological nano dye and use method thereof |
| JP2012528184A (en) | 2009-05-29 | 2012-11-12 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Methods of administration of thrombopoietin agonist compounds |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH105653A (en) * | 1922-11-11 | 1924-07-01 | Chem Ind Basel | Process for the production of a new azo dye. |
| GB691475A (en) * | 1950-04-24 | 1953-05-13 | Ici Ltd | New azo colouring matters |
| CH428031A (en) * | 1962-08-02 | 1967-01-15 | Geigy Ag J R | Process for the production of azo dyes which are sparingly soluble in water |
| NL129886C (en) * | 1965-03-17 | |||
| GB1239548A (en) * | 1969-03-06 | 1971-07-14 | ||
| JPS4996010A (en) * | 1972-10-03 | 1974-09-11 | ||
| US3905952A (en) * | 1972-10-30 | 1975-09-16 | Du Pont | Orange phenylazoazobenzene acid dye |
| JPS5067841A (en) * | 1973-10-19 | 1975-06-06 | ||
| DE2503791C2 (en) * | 1975-01-30 | 1977-03-10 | Hoechst Ag | METHOD FOR MANUFACTURING LACQUERED AZO DYES |
| GB1488599A (en) * | 1975-05-16 | 1977-10-12 | Yorkshire Chemicals Ltd | Water-soluble monoazo dyes |
| US4045425A (en) * | 1976-02-19 | 1977-08-30 | E. I. Du Pont De Nemours And Company | Crystalline azopyrazolone acid dye |
| DE2616981C2 (en) * | 1976-04-17 | 1983-12-08 | Basf Ag, 6700 Ludwigshafen | Pyrazolone azo dyes, their manufacture and use |
| JPS5337732A (en) * | 1976-09-20 | 1978-04-07 | Nippon Kayaku Co Ltd | Monoazo lake, its preparation and coloring therewith |
| DE3133404A1 (en) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | LACQUERED LACQUERED AZO COLORED SUBSTANCES |
| IT1153467B (en) * | 1982-02-22 | 1987-01-14 | Montefluos Spa | COMPOSITE PIGMENTS AND PROCESS FOR THEIR PREPARATION |
| DE3543512A1 (en) * | 1985-12-10 | 1987-06-11 | Bayer Ag | AZO COLOR LACQUER |
| GB2185491A (en) * | 1986-01-21 | 1987-07-22 | Ciba Geigy Ag | New azo pigments and their production |
| DE3789185D1 (en) * | 1986-10-03 | 1994-04-07 | Ciba Geigy | Mixed crystals from lacquered azo dyes. |
| DE3833226A1 (en) * | 1988-09-30 | 1990-04-05 | Hoechst Ag | MONOAZOPIGMENT, METHOD FOR THE PRODUCTION AND USE THEREOF |
| DE4111348A1 (en) * | 1991-04-09 | 1992-10-15 | Sandoz Ag | New metal lake of diazo cpd. used as pigment - prepd. from amino chloromethyl or di:chlorobenzene sulphonic acid and sulpho-phenyl methyl pyrazolone |
| US5482546A (en) * | 1994-03-30 | 1996-01-09 | Canon Kabushiki Kaisha | Dye, ink containing the same, and ink-jet recording method and instrument using the ink |
-
1995
- 1995-02-13 US US08/387,994 patent/US5746821A/en not_active Expired - Lifetime
-
1996
- 1996-01-31 WO PCT/US1996/001240 patent/WO1996025464A1/en active Application Filing
- 1996-01-31 AU AU48609/96A patent/AU4860996A/en not_active Abandoned
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