DE2428199A1 - Azo pigments from 2-alkyl sulphonyl 4-nitroaniline - as diazo component, coupled with 2,4-diamino 6-hydroxy pyrimidine - Google Patents
Azo pigments from 2-alkyl sulphonyl 4-nitroaniline - as diazo component, coupled with 2,4-diamino 6-hydroxy pyrimidineInfo
- Publication number
- DE2428199A1 DE2428199A1 DE19742428199 DE2428199A DE2428199A1 DE 2428199 A1 DE2428199 A1 DE 2428199A1 DE 19742428199 DE19742428199 DE 19742428199 DE 2428199 A DE2428199 A DE 2428199A DE 2428199 A1 DE2428199 A1 DE 2428199A1
- Authority
- DE
- Germany
- Prior art keywords
- diamino
- nitroaniline
- azo pigments
- coupled
- alkyl sulphonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 6
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 title claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 2
- 238000004040 coloring Methods 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 239000000976 ink Substances 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 230000008878 coupling Effects 0.000 claims abstract 2
- 238000010168 coupling process Methods 0.000 claims abstract 2
- 238000005859 coupling reaction Methods 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims description 8
- 239000003973 paint Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000004922 lacquer Substances 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 238000009987 spinning Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SLSWVEQLCOSOTJ-UHFFFAOYSA-N 2,6-diamino-1h-pyrimidin-4-one;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC(=O)N=C(N)N1 SLSWVEQLCOSOTJ-UHFFFAOYSA-N 0.000 description 1
- CVQZTMZHMYOEGV-UHFFFAOYSA-N 2-ethylsulfonyl-4-nitroaniline Chemical compound CCS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1N CVQZTMZHMYOEGV-UHFFFAOYSA-N 0.000 description 1
- KIMXIMWZIRTKCQ-UHFFFAOYSA-N 2-methylsulfonyl-4-nitroaniline Chemical group CS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1N KIMXIMWZIRTKCQ-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000013550 pizza Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
- C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Pizmentfarbstoffe Die Erfindung betrifft die Farbstoffe der Formel in der R Athyl oder vorzugsweise Methyl ist.Pizza dyes The invention relates to the dyes of the formula in which R is ethyl or preferably methyl.
Die Farbstoffe haben ausgezeichnete Pigmenteigenschaften.The dyes have excellent pigment properties.
Insbesondere zeigen sie bei brillantem Voll ton sehr gute Licht- und Wetterechtheit und sehr hohes Deckvermögen, so daß sie besonders zur Färbung von Auto- und Industrielacken geeignet sind. Die Farbstoffe können aufgrund ihrer guten Echtheiten auch zum Färben von Kunststoffen, wie Gummi, PVC, Polystyrol, zur Herstellung von Druckfarben, zum Spinnfårben oder zu anderen bekannten Pigmentverwendungszwecken benutzt werden.In particular, they show very good light and color with a brilliant full tone Weather fastness and very high hiding power, making them particularly suitable for coloring Car and industrial paints are suitable. The dyes can be due to their good Fastness properties also for coloring plastics such as rubber, PVC, polystyrene, for manufacturing from printing inks, spin dyeing, or other known pigment uses to be used.
Die Herstellung der Farbstoffe erfolgt auf an sich bekannte Weise durch Diazotieren von 2-Methyl- oder 2-Athylsulfonyl-4-nitranilin und Kuppeln auf 2,4-Diamino-6-hydroxypyrimidin.The dyes are produced in a manner known per se by diazotizing 2-methyl- or 2-ethylsulfonyl-4-nitroaniline and domes 2,4-diamino-6-hydroxypyrimidine.
Nach der Abtrennung können die Farbstoffe gegebenenfalls in an sich bekannter Weise in eine physikalische Form Uberftihrt werden, die der gewünschten speziellen Verwendung am besten angepaßt ist.After the separation, the dyes can, if appropriate, per se can be converted into a physical form which is the desired one in a known manner is best adapted to specific use.
Beispiel 21,6 g p-Nitranilin-o-methylsulfon werden bei.O bis 500 in 46 g 98 kige Schwefelsäure eingetragen, dann werden 29 g 45 ziege Nitrosylschwefelsäure zugetropSt, und es wird 6 Stunden gerührt. Die Lösung wird dann unter kräftigem Rühren auf 150 g Eis getropft. Die so erhaltene Diazolösung wird zu einer Suspension von 21,8 g 2,4-Diamino-6-hydroxypyrimidinsulfat, 9 g Natriumhydroxid und 10 g Natriumacetat in 350 ml Wasser zugetropft und kräftig gerührt. Example 21.6 g of p-nitroaniline-o-methylsulfone are added at. 0 to 500 entered in 46 g of 98 kige sulfuric acid, then 29 g 45 goat Nitrosylsulfuric acid is added dropwise, and the mixture is stirred for 6 hours. The solution will be then added dropwise to 150 g of ice with vigorous stirring. The diazo solution thus obtained becomes a suspension of 21.8 g of 2,4-diamino-6-hydroxypyrimidine sulfate, 9 g of sodium hydroxide and 10 g of sodium acetate in 350 ml of water were added dropwise and stirred vigorously.
Nach dreistündigem Rühren wird abgesaugt und mit Wasser gewaschen. Das Filtergut wird in 200> ml Wasser suspendiert und 3 Stunden bei 950C gerührt, danach abgesaugt, gewaschen und getrocknet. Man erhält so 31 g eines orange gefärbten Pigments, das beim Einfärben in Lack eine brillante, sehr stark deckende, licht-, wetter- und überspritzechte Orangefärbung ergibt,After three hours of stirring, it is filtered off with suction and washed with water. The filter material is suspended in 200 ml of water and stirred for 3 hours at 950C, then suctioned off, washed and dried. This gives 31 g of an orange colored one Pigments, which, when colored in lacquer, produce a brilliant, very opaque, light, weather and oversprayed orange color results,
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742428199 DE2428199A1 (en) | 1974-06-11 | 1974-06-11 | Azo pigments from 2-alkyl sulphonyl 4-nitroaniline - as diazo component, coupled with 2,4-diamino 6-hydroxy pyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742428199 DE2428199A1 (en) | 1974-06-11 | 1974-06-11 | Azo pigments from 2-alkyl sulphonyl 4-nitroaniline - as diazo component, coupled with 2,4-diamino 6-hydroxy pyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2428199A1 true DE2428199A1 (en) | 1976-01-02 |
Family
ID=5917874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742428199 Pending DE2428199A1 (en) | 1974-06-11 | 1974-06-11 | Azo pigments from 2-alkyl sulphonyl 4-nitroaniline - as diazo component, coupled with 2,4-diamino 6-hydroxy pyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2428199A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8013045B2 (en) | 2006-10-25 | 2011-09-06 | BASF SE Ludwigshafen | Monoazo colorants for mass-colouring of polymers |
-
1974
- 1974-06-11 DE DE19742428199 patent/DE2428199A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8013045B2 (en) | 2006-10-25 | 2011-09-06 | BASF SE Ludwigshafen | Monoazo colorants for mass-colouring of polymers |
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