CH154708A - Process for the preparation of a dye. - Google Patents
Process for the preparation of a dye.Info
- Publication number
- CH154708A CH154708A CH154708DA CH154708A CH 154708 A CH154708 A CH 154708A CH 154708D A CH154708D A CH 154708DA CH 154708 A CH154708 A CH 154708A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- production
- preparation
- parts
- dinitraniline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 229920003086 cellulose ether Polymers 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002966 varnish 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 149405. Verfahren zur Darstellung eines Farbstoffes. Im Hauptpatent ist ein Verfahren zur Darstellung eines Azofarbstoffes beschrieben, bei dem diazotiertes p-Nitranilin mit Äthyl- (c)-oxäthyl)-ariiliri gekuppelt wird.
Es wurde nur) gefunden, dass man in analoger Weise ebenfalls einen Azofarbstoff mit wertvollen Eigenschaften erhält, wenn man 2 . 4. Dinitranilin diazotiert und die er haltene Diazoverbindung mit Ogäthyl-ri-butyl- anilin kuppelt.
Der Farbstoff bildet beim Kristallisieren aus Alkohol schwarze, metallisch glänzende Nädelchen, welche sich in konzentrierter Schwefelsäure blaurot lösen, und färbt Cellulo- seester und -äther in rotvioletten Tönen; er eignet sich auch zur Herstellung von gefärbten Zapon- und Spirituslacken. <I>Beispiel:</I> 37 Teile 2.4-Dinitranilin werden in 100 Teilen 96o/oiger Schwefelsäure unter Rühren gelöst.
Man kühlt auf 511 C ab und versetzt mit einer Menge Nitrosylscbwefelsäure, welche 9,4 Teilen HN02 entspricht. Nachdem die Diazotierung beendet ist, lässt man die schwefel saure Lösung einlaufen in eine Lösung von 40 Teilen Oxäthyl-n-butylanilin, erhältlich zum Beispiel durch Einwirkung von Glykol- chlorhydrin oder von Äthylenoxyd auf Mono- n-butylanilin, und 30 Teilen 30 /oiger Salz säure in 4000 Teilen Wasser, deren Temperatur mit Hilfe von Eis auf etwa 0 C gehalten wird.
Kurze Zeit nach dem Einlaufen der Diazoverbindung ist die Farbstoffbildung be endet. Man saugt ab und wäscht solange mit Wasser nach, bis das Filtrat neutral reagiert. Der Farbstoff' wird darin entweder in eine zum Färben geeignete Pastenform gebracht oder bei etwa<B>500</B> C getrocknet.
Additional patent to main patent No. 149405. Process for the preparation of a dye. The main patent describes a process for the preparation of an azo dye in which diazotized p-nitroaniline is coupled with ethyl- (c) -oxäthyl) -ariiliri.
It has only been found that an azo dye with valuable properties is also obtained in an analogous manner if 2. 4. Dinitraniline is diazotized and the diazo compound obtained is coupled with Ogäthyl-ri-butyl aniline.
When crystallizing from alcohol, the dye forms black needles with a metallic sheen, which dissolve in concentrated sulfuric acid in a bluish red color, and dyes cellulose esters and ethers in red-violet tones; it is also suitable for the production of colored zapon and spirit varnishes. <I> Example: </I> 37 parts of 2,4-dinitraniline are dissolved in 100 parts of 96% sulfuric acid with stirring.
It is cooled to 511 ° C. and mixed with an amount of nitrosylsulfuric acid which corresponds to 9.4 parts of HNO2. After the diazotization is complete, the acidic sulfuric solution is allowed to run into a solution of 40 parts of oxethyl-n-butylaniline, obtainable, for example, by the action of glycol chlorohydrin or of ethylene oxide on monon-n-butylaniline, and 30 parts of 30% Hydrochloric acid in 4000 parts of water, the temperature of which is kept at about 0 C with the help of ice.
A short time after the diazo compound has run in, dye formation is over. It is filtered off with suction and washed with water until the filtrate has a neutral reaction. The dyestuff is either brought into a paste form suitable for dyeing or dried at about <B> 500 </B> C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH154708T | 1931-06-09 | ||
| CH149405T | 1932-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH154708A true CH154708A (en) | 1932-05-15 |
Family
ID=25715411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH154708D CH154708A (en) | 1931-06-09 | 1931-06-09 | Process for the preparation of a dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH154708A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE916968C (en) * | 1952-03-20 | 1954-08-23 | Basf Ag | Process for the production of azo waste |
-
1931
- 1931-06-09 CH CH154708D patent/CH154708A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE916968C (en) * | 1952-03-20 | 1954-08-23 | Basf Ag | Process for the production of azo waste |
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