CH258298A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH258298A CH258298A CH258298DA CH258298A CH 258298 A CH258298 A CH 258298A CH 258298D A CH258298D A CH 258298DA CH 258298 A CH258298 A CH 258298A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- pyrazolone
- mol
- production
- new
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 239000000987 azo dye Substances 0.000 title description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- FROLMIGPHKATQS-UHFFFAOYSA-N 2-amino-5-benzamidobenzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1NC(=O)C1=CC=CC=C1 FROLMIGPHKATQS-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 241000219146 Gossypium Species 0.000 claims 1
- -1 azo compound Chemical class 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 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
- 239000002002 slurry Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, d@ass man einen neuen Azofarbstoff erhält, wenn man 2 Mol des Pyrazolors .der Formel
EMI0001.0008
1 Mol Phosgen und 2 Mol diazotie:
rte 5-Ben- zoyla.mino-2-aminobenzol-l-karbonsäure der art .aufeinander zur Einwirkung bringt, dass 2 Mol des Pyrazolonsj zu einem H,a.rnetoff- derivat vereinigt werden und die. Diazaver- bindung in 4-Stellung des Pyrazolonkerns eingreift.
Der neue Farbstoff .stellt ein braungelbes Pulver dar, weilches sich in wässeriger ver dünnter Sofialösung und in konzentrierter Schwefelsäure mit orangegelber Farbe lök Er färbt Baumwolle und regenerierte Zellu lose in rotgelben Tönen an, welche durch Nachbehandeln mit kupferabgebenden Mit teln hervorragend wasch- unid lichtecht wer den.
<I>Beispiel 1:</I> 45 Teile des Pyrazolonderivates der Foir- mel
EMI0001.0034
werden in 500 Teilen Wasser und 11 Teilen Natriumkarbonat gelöst und durch Einleiten von Phosgen bei einer Temperatur von 40 bis 50 in den Harnstoff übergeführt. Nach dem Verschwinden der freien Aminogruppe wird der Harnstoff abgetrennt.
25 Teile 5-Benzoylamino-2-aminobenzol-1- karbaneäure werden in etwa 200 Teilen Wasser, unter Zusatz von 4 Teilen Natrium- hydro.xyd, gelöst. In diese Lösung gibt man 7 Teile Natriumnitrit. Alsdann lässt man dieses Gemisch in eine eisgekühlte, Lösung von etwa 100 Teilen Walsee und 40 Teilen Salzsäure (d =1,115) einlaufen.
Nach etwa 2 Stunden ist die Diazotierung beendet und ,die Ditazoverbindung zum grössten Teil aus gefallen. Den Diazobrei lässt man unter gutem Rühren, in. eine durch Eis auf etwe 5 abgekühlte Lösung, enthaltend 46,4 Teile des nach dem 1. Absatz dieses Beispiels er hältlichen Harnstoffes und 50 Teile Na triumkarbonat, einlaufen.
Man rührt bis zur beendigten Kupplung. Man erwärmt das Gemisch noch auf etwa 70 auf und fällt den gebildeten Disazofarb- stoff durch Zusiatz von Kochsalz aus. Nach crem Erkalten wird der Farbstoff abge- nutscht und getrocknet.
<I>Beispiel 2:</I> 25 Teile 5-Benzoylamino-2-aminobenzol- 1-karbonsäurs werden in etwa. 200 Teilen Wassier, unter Zusatz von 4 Teilen Natrium- hydrogyd, gelöst. In diese Lösung gibt man 7 Teile Naüriumn,,trit. Alsdann lässt man dieses Gemisch in eine eisgekühlte Lösung von etwa 100 Teilen Wasser und 40 Teilen Salzsäure (d =<B>1.,115)</B> einlaufen.
Nach etwa; 2 Stunden iot die Diazotierung beendigt und die Diazoverbindung zum grössten Teil ausgefallen.
Der Diazobrei wird in eine Lösung, ent haltend in etwa 500 Teilen Wasser 45,1 Teile des Pyrazolons der Formel
EMI0002.0034
und 2'5 Teile Natriumkarbonat, gegeben.
Nach. beendigter Kupplung wird auf etwa 50 erwärmt und der gebildete Aminoazo- farbsitoff durch Einleiten von Phosgen und Abstumpfen -der frei werdenden Säure in den entsprechenden Harnstoff übergeführt. Wenn in der Reaktionsmasse keine freie Aminogrurpipa mehr festgesteint werden kann, wird der Farbstoff, nach Zusatz von Koch salz, nasch dem Abkühlen abgenutscht.
Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 2 mol of the pyrazolor of the formula
EMI0001.0008
1 mole of phosgene and 2 moles of diazotism:
rte 5-benzoyla.mino-2-aminobenzene-1-carboxylic acid of the kind. brings about an action on each other that 2 moles of the pyrazolone are combined to form a hydrogen derivative and the. Diaza compound engages in position 4 of the pyrazolone nucleus.
The new dye is a brownish-yellow powder because it dissolves in diluted aqueous sofia solution and in concentrated sulfuric acid with an orange-yellow color. It stains cotton and regenerated cellulose in red-yellow tones, which are extremely washable and lightfast when treated with copper-releasing agents the.
<I> Example 1 </I> 45 parts of the pyrazolone derivative of the Foirel
EMI0001.0034
are dissolved in 500 parts of water and 11 parts of sodium carbonate and converted into urea by introducing phosgene at a temperature of 40 to 50. After the free amino group has disappeared, the urea is separated off.
25 parts of 5-benzoylamino-2-aminobenzene-1-carbanic acid are dissolved in about 200 parts of water with the addition of 4 parts of sodium hydroxide. 7 parts of sodium nitrite are added to this solution. This mixture is then allowed to run into an ice-cold solution of about 100 parts of Walsee and 40 parts of hydrochloric acid (d = 1.115).
After about 2 hours, the diazotization has ended and most of the ditazo compound has precipitated out. The diazo slurry is allowed to run, with thorough stirring, into a solution cooled to about 5 by ice, containing 46.4 parts of the urea obtainable according to the 1st paragraph of this example and 50 parts of sodium carbonate.
The mixture is stirred until the coupling is complete. The mixture is warmed up to about 70 and the disazo dye formed is precipitated by adding sodium chloride. After it has cooled to a creamy temperature, the dye is filtered off with suction and dried.
<I> Example 2: </I> 25 parts of 5-benzoylamino-2-aminobenzene-1-carboxylic acid are approximately. 200 parts of Wassier, with the addition of 4 parts of sodium hydroxide, dissolved. 7 parts of Naüriumn are added to this solution. This mixture is then allowed to run into an ice-cold solution of about 100 parts of water and 40 parts of hydrochloric acid (d = 1., 115).
After about; 2 hours iot the diazotization ended and the diazo compound precipitated for the most part.
The diazo slurry is in a solution containing 45.1 parts of the pyrazolone of the formula in about 500 parts of water
EMI0002.0034
and 2'5 parts of sodium carbonate.
To. When the coupling is complete, it is heated to about 50 and the aminoazo-dye formed is converted into the corresponding urea by introducing phosgene and blunting the acid released. If no more free aminogrurpipa can be stoned in the reaction mass, the dye is sucked off after the addition of cooking salt after cooling.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH258298T | 1942-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH258298A true CH258298A (en) | 1948-11-30 |
Family
ID=4472562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH258298D CH258298A (en) | 1942-03-18 | 1942-03-18 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH258298A (en) |
-
1942
- 1942-03-18 CH CH258298D patent/CH258298A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH258298A (en) | Process for the production of a new azo dye. | |
| CH119898A (en) | Process for the production of a new dye. | |
| CH119901A (en) | Process for the production of a new dye. | |
| CH232825A (en) | Process for the preparation of an azo dye. | |
| CH228936A (en) | Process for the production of a new azo dye. | |
| CH177820A (en) | Process for the production of a new azo dye. | |
| CH220110A (en) | Process for the production of a new azo dye. | |
| CH146754A (en) | Process for the production of a new azo dye. | |
| CH302027A (en) | Process for the preparation of a trisazo dye. | |
| CH253877A (en) | Process for the production of a new azo dye. | |
| CH139651A (en) | Process for the preparation of a polyazo dye. | |
| CH237130A (en) | Process for the production of a new azo dye. | |
| CH302028A (en) | Process for the preparation of a trisazo dye. | |
| CH192851A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH220107A (en) | Process for the production of a new azo dye. | |
| CH283992A (en) | Process for the preparation of a trisazo dye. | |
| CH293362A (en) | Process for the preparation of a substantive azo dye. | |
| CH211838A (en) | Process for the preparation of an azo dye. | |
| CH296539A (en) | Process for the preparation of a trisazo dye. | |
| CH268075A (en) | Process for the preparation of an azo dye. | |
| CH137648A (en) | Process for the preparation of an azo dye. | |
| CH197582A (en) | Process for the production of a new azo dye. | |
| CH173064A (en) | Process for the production of a new azo dye. | |
| CH200674A (en) | Process for the preparation of a metal-containing azo dye. | |
| CH199786A (en) | Process for the preparation of a new, water-soluble monoazo dye. |