DE402869C - Process for the preparation of monoazo dyes - Google Patents
Process for the preparation of monoazo dyesInfo
- Publication number
- DE402869C DE402869C DEF53328D DEF0053328D DE402869C DE 402869 C DE402869 C DE 402869C DE F53328 D DEF53328 D DE F53328D DE F0053328 D DEF0053328 D DE F0053328D DE 402869 C DE402869 C DE 402869C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- nitro
- weight
- parts
- monoazo dyes
- 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.)
- Expired
Links
- 239000000975 dye Substances 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
- 238000000034 method Methods 0.000 title claims description 3
- 239000000835 fiber Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical group C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001043 yellow dye 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
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung von 1Vlonoazofarbstoffen. Es wurde gefunden, daß man für die Lackbereitung und zur Erzeugung auf der Faser geeignete Monoazofarbstoffe dadurch erhält, daß Diazoverbindungen der Nitraniline oder ihrer Derivate, wie z. B. q.-Chlor- oder a.-Methyl-2-nitranilin, 4-Nitro-2-methoxyanilin mit Acetessig-5-nitro-q.-chlor-2-anisidid gekuppelt werden.Process for the preparation of 1Vlonoazo dyes. It was found, that one can use monoazo dyes suitable for lacquer preparation and production on the fiber obtained in that diazo compounds of nitroanilines or their derivatives, such as. B. q.-chloro- or a.-methyl-2-nitroaniline, 4-nitro-2-methoxyaniline with acetoacetic-5-nitro-q.-chloro-2-anisidide be coupled.
Die neuen Farbstoffe sind wasserunlösliche Produkte, die auf Substraten gelbe Lacke von außerordentlicher Klarheit ergeben, welche sich durch ihren grünstichigen Farbton auszeichnen. Sie sind vorzüglich geeignet für Leim-, Öl- und Druckfarben; als solche sind sie wasserecht, ölecht und vorzüglich lichtecht. Sie können auch auf der Faser erzeugt werden.The new dyes are water-insoluble products on substrates yellow lacquers of extraordinary clarity, which are characterized by their greenish tint Distinguish the color. They are particularly suitable for glue, oil and printing inks; as such they are water-proof, oil-proof and especially lightfast. You can also can be generated on the fiber.
Das Acetessig-5-nitro-4-chlor-2-anisidid vom Schmelzpunkt 126 bis i27° erhält man, indem man 5-Nitro-q.-chlor-2-anisidin mit Acetessigester für sich oder in einem indifferenten Lösungsmittel erhitzt. Beispiel i. i38 Gewichtsteile o-Nitranilin werden in bekannter `'eise diazotiert, die Diazolösung mit Natriumacetatlösung essigsauer gemacht und dann unter Rühren mit einer Lösung von 286"q Gewichtsteilen Acetessig-5-nitro-q-chlor-2-anisidid in der zehnfachen Menge Eisessig versetzt. Nach Beendigung der Kuppelung saugt man den gelben Farbstoff ab, wäscht mit Wasser nach und verwendet den Farbstoff für die Lackherstellung als Paste oder nach dem Trocknen als Pulver in bekannter `'eise. Die Kupplung kann man auch bei Gegenwart eines Substrates vornehmen. Beispiel 2. 8 Gewichtsteile Acetessig-5-nitro-q.-chlor-2-anisidid werden mit ieeo Gewichtsteilen heißem Wasser übergossen, dann fügt man io Gewichtsteile Natronlauge von 38° B6 unter Rühren hinzu, wobei sich das Acetessig-5-nitro-q-chlor-2-anisidid mit gelbroter Farbe auflöst. Nach Zugabe von 25 Gewichtsteilen Türkischrotöl und ico Gewichtsteilen gesättigter Kochsalzlösung zieht man 5o Gewichtsteile Baumwolle einige Minuten bei 3o bis 40 ' durch, quetscht gut ab und kuppelt, wie üblich, in einer mit Natriumacetat abgestumpften Diazolösung von o-Nitranilin; darauf spült man, seift kochend 1/s Stunde, spült und trocknet.The acetoacetic 5-nitro-4-chloro-2-anisidide with a melting point of 126 ° to i27 ° is obtained by heating 5-nitro-q.-chloro-2-anisidine with acetoacetic ester alone or in an inert solvent. Example i. 38 parts by weight of o-nitroaniline are diazotized in the known manner, the diazo solution is made acetic acid with sodium acetate solution and then ten times the amount of glacial acetic acid is added to a solution of 286 parts by weight of acetoacetic-5-nitro-q-chloro-2-anisidide After the coupling is complete, the yellow dye is suctioned off, washed with water and used for the paint production as a paste or, after drying, as a powder in the known manner. The coupling can also be carried out in the presence of a substrate. Example 2 8 parts by weight of acetoacetic acid-5-nitro-q.-chloro-2-anisidide are poured over with ieeo parts by weight of hot water, then 10 parts by weight of sodium hydroxide solution at 38 ° B6 are added with stirring, the acetoacetic acid-5-nitro-q- chlorine-2-anisidide dissolves with a yellow-red color. After adding 25 parts by weight of Turkish red oil and ico parts by weight of saturated sodium chloride solution, 50 parts by weight of cotton are drawn through for a few minutes at 3o to 40 ', qu Etch off well and, as usual, couple in a diazo solution of o-nitroaniline blunted with sodium acetate; then one rinses, soaps at the boil for 1 / s hour, rinses and dries.
Auf diese Weise erhält man auf der Faser ein klares grünstichiges Gelb, das gut wasch- und kochecht ist.In this way you get a clear greenish tinge on the fiber Yellow, which is washable and boil-proof.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF53328D DE402869C (en) | 1923-01-25 | 1923-01-25 | Process for the preparation of monoazo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF53328D DE402869C (en) | 1923-01-25 | 1923-01-25 | Process for the preparation of monoazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE402869C true DE402869C (en) | 1924-09-19 |
Family
ID=7106206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF53328D Expired DE402869C (en) | 1923-01-25 | 1923-01-25 | Process for the preparation of monoazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE402869C (en) |
-
1923
- 1923-01-25 DE DEF53328D patent/DE402869C/en not_active Expired
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