CH133801A - Process for the preparation of an insoluble monoazo dye. - Google Patents
Process for the preparation of an insoluble monoazo dye.Info
- Publication number
- CH133801A CH133801A CH133801DA CH133801A CH 133801 A CH133801 A CH 133801A CH 133801D A CH133801D A CH 133801DA CH 133801 A CH133801 A CH 133801A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- monoazo dye
- insoluble monoazo
- valuable
- insoluble
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 4
- 239000003292 glue Substances 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- VEIXVSPCPGWULB-UHFFFAOYSA-N 1-(4-amino-3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 VEIXVSPCPGWULB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- LCYPETFMWVGRSA-UHFFFAOYSA-N n-chloro-3-oxo-n-phenylbutanamide Chemical compound CC(=O)CC(=O)N(Cl)C1=CC=CC=C1 LCYPETFMWVGRSA-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines unlöslichen 3Ionoazofarbstoffes. Es wurde gefunden, dass man sehr wert volle grünstichig gelbe Pigmentfarbstoffe da durch erhält, dass man Aminoverbindungen folgender allgemeiner Formel:
EMI0001.0005
worin R ein aromatischer oder aliphatischer Rest sein kann, diazotiert und mit Acetessig- säureaniliden kuppelt.
Die Diazotierkompo- nente kann hierbei noch weiter, zum Beispiel durch Halogen, Nitro- oder Methoxygruppen substituiert sein, wie auch im Acetessigsäure- anilid ein teilweiser Ersatz der Wasserstoff atome des Anilinrestes durch ähnliche Sub- stituenten stattfinden kann.
Die Nuance kann durch Einführung derartiger Substituerrten in geringem Umfang verändert werden, unter Erhaltung der wertvollen allgemeinen Eigen schaften, die durch die CO-Gruppe im Mole kül der Diazotierkomponente bedingt sind.
Die neuen Farbkörper bilden als Öl- wie als Leimfarben eine wertvolle Erweiterung der Reihe der bisher vorhandenen Produkte nach der grünen Seite des Spektrums hin.
Gegenstand vorliegenden Patentes ist ein Verfahren zur Darstellung eines . solchen un löslichen Monoazofarbstoffes; das Verfahren ist dadurch gekennzeichnet, dass man die Diazoverbindung aus 4-Amino-3-nitro-aceto- phenon mit Acetessigsäureorthochlorairilid kuppelt.
Der so erhaltene, grünstichig gelbe Pig mentfarbstoff ist sehr wertvoll als Lack-, Öl- und als Leimfarbe.
<I>Beispiel:</I> 180 Gewichtsteile 4-Amino-3-nitro-aceto- phenon werden mit der berechneten Menge Nitrit und Salzsäure diazotiert und die Diazo- lösung unter Umrühren in die Lösung von 212 Gewichtsteilen Acetessigsäureorthochlor- anilid und von 200 Gewichtsteilen wasser freiem Natriumacetat in 2000 Gewichtsteilen Eisessig gegeben. Nach beendeter Kupplung wird abfiltriert und gewaschen.
Anstatt .der Kupplung in Eisessig; kann man auch in wässeriger Lösung arbeiten in der Weise, dass man das Acetessigsäurechlor- anilid erst mit Natronlauge in Lösung bringt und dann vorsichtig so viel Essigsäure zu setzt, bis eben eine Abscheidung des Acet- essigsäurechloranilids zu sehen ist.
Process for the preparation of an insoluble 3ionoazo dye. It has been found that very valuable greenish yellow pigment dyes are obtained by using amino compounds with the following general formula:
EMI0001.0005
where R can be an aromatic or aliphatic radical, diazotized and coupled with acetoacetic anilides.
The diazotization component can be further substituted, for example by halogen, nitro or methoxy groups, and in acetoacetic anilide the hydrogen atoms of the aniline residue can also be partially replaced by similar substituents.
The shade can be changed to a small extent by introducing such substituents, while maintaining the valuable general properties which are caused by the CO group in the molecule of the diazotization component.
As oil and glue colors, the new pigments form a valuable extension of the range of previously available products on the green side of the spectrum.
The present patent is a method for the preparation of a. such insoluble monoazo dye; the process is characterized in that the diazo compound from 4-amino-3-nitro-acetophenone is coupled with acetoacetic acid orthochloride.
The greenish-tinged yellow pigment obtained in this way is very valuable as a paint, oil and glue paint.
<I> Example: </I> 180 parts by weight of 4-amino-3-nitro-aceto-phenone are diazotized with the calculated amount of nitrite and hydrochloric acid and the diazo solution is added to the solution of 212 parts by weight of acetoacetic acid orthochloro anilide and 200 while stirring Parts by weight of anhydrous sodium acetate in 2000 parts by weight of glacial acetic acid. After the coupling has ended, it is filtered off and washed.
Instead of the coupling in glacial acetic acid; You can also work in aqueous solution in such a way that you first bring the acetoacetic acid chloranilide into solution with sodium hydroxide solution and then carefully add enough acetic acid until a separation of the acetoacetic acid chloranilide can be seen.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE133801X | 1926-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH133801A true CH133801A (en) | 1929-06-30 |
Family
ID=5665163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH133801D CH133801A (en) | 1926-12-03 | 1927-11-29 | Process for the preparation of an insoluble monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH133801A (en) |
-
1927
- 1927-11-29 CH CH133801D patent/CH133801A/en unknown
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