CH302049A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH302049A CH302049A CH302049DA CH302049A CH 302049 A CH302049 A CH 302049A CH 302049D A CH302049D A CH 302049DA CH 302049 A CH302049 A CH 302049A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation
- sulfonic acid
- cyanuric
- remaining
- chlorine atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 2
- -1 aminomonoazo Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J25/00—Transit-time tubes, e.g. klystrons, travelling-wave tubes, magnetrons
- H01J25/34—Travelling-wave tubes; Tubes in which a travelling wave is simulated at spaced gaps
- H01J25/36—Tubes in which an electron stream interacts with a wave travelling along a delay line or equivalent sequence of impedance elements, and without magnet system producing an H-field crossing the E-field
- H01J25/38—Tubes in which an electron stream interacts with a wave travelling along a delay line or equivalent sequence of impedance elements, and without magnet system producing an H-field crossing the E-field the forward travelling wave being utilised
-
- 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
-
- 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
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Microwave Tubes (AREA)
- Coloring (AREA)
- Particle Accelerators (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 298139. Verfahren zur Herstellung eines Disazofarbstoffes.
Es wurde gefunden, dass man zu einem wertvollen Disazofarbstoff gelangt, w die Aminomonoazofarbstoffe der Formeln
EMI0001.0006
mittels Cyanurehlorid miteinander konden siert und das noch verbleibende dritte an den Cyanurring gebundene Chloratom durch den Rest der Aminobenzol-3-sulfonsäure ersetzt.
Der neue Farbstoff bildet ein gelbes Pul ver, das sich in Wasser mit gelber Farbe löst und Baumwolle und regenerierte Cellulose in sehr reinen, gelben Tönen anfärbt. Nach dem ein- oder zweibadigen Naehkupferungsverfah- ren erhält man gelbe Töne von sehr guter Nass- und Lichtechtheit.
Die Vereinigung der beiden Aminomono- azofa.rbstoffe mittels Cyanurehlorid und der Ersatz des noch verbleibenden dritten an den Cy anurring gebundenen Chloratoms durch den Rest der Aminobenzol-3-sulfonsäure er folgen zweckmässig in wässerigem, schwach alkalischem Medium. Es empfiehlt sich, den H- Vert und/oder die Umsetzungstemperatur P<B>N</B> bei jeder Kondensationsstufe gegenüber der vorhergehenden zu erhöhen.
Beispiel: Eine Lösung aus 49 Teilen 4'-(4"-Amino)- b enzoylamino - 2' - chlor - 4-oxy-1,1'-azobenzol-3- carbonsäure-5-sulfonsäure und 10,6 Teilen Na triumcarbonat in 2000 Teilen Wasser giesst man bei 5 innert 10 Minuten zu einer Auf- schlämmung von 18,4 Teilen Cyanurchlorid in wenig Eiswasser und neutralisiert die ent stehende Salzsäure mit einer Lösung von 8,4 Teilen Natriumbicarbonat in 30 Teilen Was ser.
Nach eine Stunde ist die Kondensation beendet. Hierauf giesst man eine 40 warme Lösung von 37,1 Teilen 4'-Amino-2'-ehlor-4- oxy-1,1'- azobenzol-3-carbonsäure-5-sulfonsäure in 1000 Teilen Wasser zu und hält die Tem peratur 12 Stunden unter gutem Rühren bei 30 bis 35 . Während dieser Zeit tropft man die Lösung von 10 Teilen Natriumbicarbonat in 35 Teilen Wasser zu. Anschliessend giesst man 37 Teile Anilin-3-sulfonsäure zu, erwärmt 2 Stunden auf $5 bis 90 , streut 10,6g Na- triumcarbonat zu und salzt das Kondensa tionsprodukt mit Natriumchlorid aus.
Additional patent to main patent No. 298139. Process for the production of a disazo dye.
It has been found that a valuable disazo dye is obtained such as the amino monoazo dyes of the formulas
EMI0001.0006
condensed with each other by means of cyanuric chloride and the remaining third chlorine atom bound to the cyanuric ring is replaced by the remainder of the aminobenzene-3-sulfonic acid.
The new dye forms a yellow powder that dissolves in water with a yellow color and dyes cotton and regenerated cellulose in very pure, yellow tones. After the one or two bath sewing process, yellow shades of very good wet and light fastness are obtained.
The combination of the two aminomonoazofa dyes by means of cyanuric chloride and the replacement of the remaining third chlorine atom bound to the cyano ring by the remainder of the aminobenzene-3-sulfonic acid are expediently carried out in an aqueous, weakly alkaline medium. It is advisable to increase the H-Vert and / or the reaction temperature P <B> N </B> in each condensation stage compared to the previous one.
Example: A solution of 49 parts of 4 '- (4 "-amino) - b enzoylamino - 2' - chloro - 4-oxy-1,1'-azobenzene-3-carboxylic acid-5-sulfonic acid and 10.6 parts of sodium carbonate 2000 parts of water are poured at 5 within 10 minutes into a slurry of 18.4 parts of cyanuric chloride in a little ice water and the hydrochloric acid formed is neutralized with a solution of 8.4 parts of sodium bicarbonate in 30 parts of water.
The condensation has ended after one hour. A warm solution of 37.1 parts of 4'-amino-2'-chloro-4-oxy-1,1'-azobenzene-3-carboxylic acid-5-sulfonic acid in 1000 parts of water is then poured in and the temperature is maintained 12 hours with good stirring at 30 to 35. During this time, the solution of 10 parts of sodium bicarbonate in 35 parts of water is added dropwise. 37 parts of aniline-3-sulfonic acid are then poured in, the mixture is heated to between $ 5 and 90 for 2 hours, 10.6 g of sodium carbonate are sprinkled in and the condensation product is salted out with sodium chloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB303049X | 1949-11-08 | ||
| GB2774869X | 1949-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302049A true CH302049A (en) | 1954-09-30 |
Family
ID=26260377
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302049D CH302049A (en) | 1949-11-08 | 1951-06-11 | Process for the preparation of a disazo dye. |
| CH298139D CH298139A (en) | 1949-11-08 | 1951-06-11 | Process for the preparation of a disazo dye. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH298139D CH298139A (en) | 1949-11-08 | 1951-06-11 | Process for the preparation of a disazo dye. |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2774869A (en) |
| CH (2) | CH302049A (en) |
| GB (1) | GB671296A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2753481A (en) * | 1952-06-14 | 1956-07-03 | Sperry Rand Corp | Travelling wave oscillators |
| US2981889A (en) * | 1956-10-18 | 1961-04-25 | Gen Electric | Electron tube frequency multiplier of the traveling wave type |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL49857C (en) * | 1935-11-30 | |||
| NL62817C (en) * | 1940-05-04 | |||
| US2516944A (en) * | 1947-12-18 | 1950-08-01 | Philco Corp | Impedance-matching device |
-
1949
- 1949-11-08 GB GB28583/49A patent/GB671296A/en not_active Expired
-
1950
- 1950-11-07 US US194540A patent/US2774869A/en not_active Expired - Lifetime
-
1951
- 1951-06-11 CH CH302049D patent/CH302049A/en unknown
- 1951-06-11 CH CH298139D patent/CH298139A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US2774869A (en) | 1956-12-18 |
| CH298139A (en) | 1954-04-30 |
| GB671296A (en) | 1952-04-30 |
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