CH302046A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH302046A CH302046A CH302046DA CH302046A CH 302046 A CH302046 A CH 302046A CH 302046D A CH302046D A CH 302046DA CH 302046 A CH302046 A CH 302046A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- yellow
- phosgene
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 20
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- -1 aminomonoazo Chemical group 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FHWRLVLDNKNYGD-UHFFFAOYSA-N nitrobenzene;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=CC=C1 FHWRLVLDNKNYGD-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 298139. Verfahren zur Herstellung eines Disazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Disazofarbstoff gelangt, wenn man die Aminomonoazofarbstoffe der Formeln
EMI0001.0006
mittels Phosgen zum Harnstoffderivat ver einigt.
Der neue Farbstoff bildet ein gelbbraunes Pulver, das sieh in Wasser mit gelber Farbe löst und Baumwolle und regenerierte Cellulose in leuchtend grünstichig gelben Tönen von guter Nass- und Lichtechtheit anfärbt. Nach dein ein- oder zweibadigen Nachkupferungs- verfa.hren erhält man grünstichig gelbe Töne c-on hoher Reinheit und sehr guter Nass- und Lichtechtheit.
Die Vereinigung der beiden Aminomono- t zofarbstoffe zum asymmetrischen Harnstoff derivat mittels Phosgen erfolgt zweckmässig in wässerigem, schwach alkalischem, z. B. alkalicarbonatalkalischem, Medium bei leicht erhöhter Temperatur in Gegenwart einer Puf fersubstanz, wie beispielsweise Natriumacetat. Der für die Reaktion günstige pa-Wert liegt zwischen 9,5 und 5,5.
Beispiel: 17,25 Teile 1-Amino-2-chlor-4-nitrobenzol werden in bekannter Weise diazotiert und mit 13,8 Teilen 1-Oxybenzol-2-carbonsäure in schwach saurer bis alkalischer Lösung gekup pelt.
32,15 Teile des abgeschiedenen und ge trockneten Farbstoffes .werden in 120 Teilen rauchende Schwefelsäure mit einem Gehalt an freiem Anhydrid von 20 /o eingetragen und unter gutem Rühren 10 Stunden auf 95 bis l00 erhitzt. Nach dem Erkalten wird die Re aktionsmasse auf Eis ausgetragen, einige Stun den gerührt und filtriert. Die Farbstoffpaste wird in 350 Teilen heissem Wasser gelöst und filtriert, wobei ein kleiner \1;e11 unsiilfonierten Farbstoffes auf dem Filter bleibt..
Das Filtrat wird mit 30 01o iger Natriumhcdroxv dlösung versetzt, bis alkalische Reaktion auf Brillant gelb eintritt, und das Natriumsalz des Farb stoffes mit Natriumchlorid gefällt.
Die Farbstoffpaste wird in 500 Teilen Wasser gelöst und die Nitrogruppe mit 9,2 Teilen Natriunisulfhvdrat bei 60 bis<B>i00</B> in die Aminogruppe übergeführt, der Aminoazofarb- stoff mit Natriumehlorid abgeschieden und filtriert.
Zu der in 800 Teilen Wasser gelösten Farb- stoffpaste gibt man 16 Teile wasserfreies Na- triiunearbonat und lässt dann bei .10 bis 50 26 Teile m-Nitrobenzovlehlorid, in 50 Teilen Aceton gelöst, zufliessen. Nachdem die Kon densation beendet ist, wird der ausgefallene Farbstoff filtriert und die Nitrogruppe wie üblieli reit Natriumsulfid bei etwa 60 his 65 in die Aminogruppe übergefiiliii.
4-9 Teile des abgesehiedenen und getrock neten Farbstoffes oder eine entsprechende .Menge Farbstoffpaste und 37,1 Teile 4- Amino- 2-eh@or-@-'-ov-1,1'-azobenzol- 3'- earbonsäure-5'- sulfonsäure werden in bekannter Weise in Gegenwart i-on Natriumearbonat als säure bindendes Mittel und Natriumaeetat als Puf fersubstanz mit Phosgen behandelt,
bis keine Aminogruppe mehr nachweisbar ist. Der voll ständig ausgefallene Farbstoff wird filtriert und getrocknet.
<B> Additional patent </B> to main patent no. 298139. Process for the production of a disazo dye. It has been found that a useful disazo dye is obtained by using the amino monoazo dyes of the formulas
EMI0001.0006
united by means of phosgene to form the urea derivative.
The new dye forms a yellow-brown powder that dissolves in water with a yellow color and dyes cotton and regenerated cellulose in bright greenish yellow shades of good wet and lightfastness. After your one or two bath re-coppering process, you get greenish yellow shades of high purity and very good wet and light fastness.
The combination of the two Aminomono t zofarrebs to the asymmetric urea derivative by means of phosgene is expediently carried out in aqueous, weakly alkaline, eg B. alkaline carbonate alkaline medium at a slightly elevated temperature in the presence of a Buf fersubstanz such as sodium acetate. The pa value, which is favorable for the reaction, is between 9.5 and 5.5.
Example: 17.25 parts of 1-amino-2-chloro-4-nitrobenzene are diazotized in a known manner and kup pelt with 13.8 parts of 1-oxybenzene-2-carboxylic acid in weakly acidic to alkaline solution.
32.15 parts of the deposited and dried dyestuff are added to 120 parts of fuming sulfuric acid with a free anhydride content of 20% and heated to 95 to 100 hours with thorough stirring. After cooling, the reaction mass is poured onto ice, stirred for a few hours and filtered. The dye paste is dissolved in 350 parts of hot water and filtered, a small amount of unsilfonized dye remaining on the filter.
The filtrate is treated with 30,010 iger sodium hydroxide solution until an alkaline reaction to brilliant yellow occurs and the sodium salt of the dye is precipitated with sodium chloride.
The dye paste is dissolved in 500 parts of water and the nitro group is converted into the amino group with 9.2 parts of sodium sulfate at 60 to 100, the aminoazo dye is deposited with sodium chloride and filtered.
16 parts of anhydrous sodium carbonate are added to the dye paste dissolved in 800 parts of water and 26 parts of m-nitrobenzene chloride dissolved in 50 parts of acetone are then allowed to flow in at 10 to 50 parts. After the condensation has ended, the dyestuff which has precipitated out is filtered and the nitro group is converted into the amino group as usual with sodium sulfide at about 60 to 65.
4-9 parts of the separated and getrock designated dye or a corresponding amount of dye paste and 37.1 parts of 4- amino-2-eh @ or - @ -'-ov-1,1'-azobenzene-3'-carboxylic acid-5 '- sulfonic acid are treated with phosgene in a known manner in the presence of sodium carbonate as an acid-binding agent and sodium acetate as a buffer substance,
until no more amino groups can be detected. The completely precipitated dye is filtered and dried.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB303049X | 1949-11-08 | ||
| GB2774869X | 1949-11-08 | ||
| CH302046T | 1951-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302046A true CH302046A (en) | 1954-09-30 |
Family
ID=27178272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302046D CH302046A (en) | 1949-11-08 | 1951-06-11 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302046A (en) |
-
1951
- 1951-06-11 CH CH302046D patent/CH302046A/en unknown
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