CH220651A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH220651A CH220651A CH220651DA CH220651A CH 220651 A CH220651 A CH 220651A CH 220651D A CH220651D A CH 220651DA CH 220651 A CH220651 A CH 220651A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- mole
- weight
- parts
- mol
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 239000000047 product Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- -1 nitrobenzoyl Chemical group 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 239000000725 suspension 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
- 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)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 217241. Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, @dass man einen neuen Azofarbstoff erhält, wenn man 1 Mol Cyanur- chlorid, 1 Mol des Produktes, das erhalten wird durch Reduzieren des Acylierunb pro- duktes aus 1 Mal 1-Amino-4-(4'-amino-3'- sulfo)
-anilidoanthrachinon-2-sulfonsäure und 1 Mol p-Nitrobenzoylchlorid, 1 Mol 4-Amino- 2-methyl-4'-oxy-1,1'-azobenzol-3'-sulf o-5'-car- bansäure und 1 Mol 1-Amino-4-oxybenzol-3- carbonsäure aufeinander einwirken lässt.
Der neue Farbstoff stellt eindunkles Pulver dar, das sich in Wasser mit .grüner Farbe löst und Baumwolle in schwach alkalischem Bade in Gegenwart von Kupfersulfat und wein saurem Natrium in wasch- und lichtechten grünen Tönen färbt.
Beispiel: 48,9 Gewichtsteile 1-Amino-4-(4'-amino- 3' - sulfo) - anilidoanthrachinon - 2 - sulfonsäure werden als Dinatriumsalz in 500 Gewichts teilen Wasser unter Zusatz von 8,4 Gewichts teilen Natriumbicarbonat gelöst. Diese Lö- sung wird bei zirka 60 mit 18,5 Gewichts teilen 4-Nitrobenzoylchlorid, die mit 10 Cre- wichtsteilen Aceton versetzt wurden, behan delt.
Man reduziert das entstandene Nitro- benzoylprodukt mit 42 'Gewichtsteilen kri stallisiertem Natriumsulfid, die in 100 Ge- wichtsteilen Wasser gelöst wurden, bei 6-0 bis 70 zum ,entsprechenden Aminobenzoyl- produ'kt. 6,0,
8 Gewichtsteile des abgesehiede- nen Reduktionsproduktes werden als neutrale Lösung in 1000 Gewichtsteilen Wasser zu einer Anschlämmung von 1,8,5 Gewichtsteilen Cyanurchlorid in 500 Gewichtsteilen kaltem Wasser ;gegeben. Man hält die Temperatur 1 Stunde bei 10-15 . Die bei der Kondensa tion entstehende Salzsäure wird durch die entsprechende Menge Natriumcarbonat neu tralisiert.
Hernach werden 35,1 Gewichtsteile 4 -Amino -12 -methyl - 4' - oxy -1,1'-azobenzol-3'- sulfo-5'-carbonsäure in 1000 Gewichtsteilen warmem Wasser gelöst, zum Monokonden- sationsprodukt gegeben.
Die Temperatur wird dabei auf 40 erhöht, Nach '24 Stun- den gibt man 15 Gewiehtsteile 1-Amino--1- oxybenzol-3-carbonsäure zu und hält die Temperatur während der bleichen Zeit auf <B>80'.</B> Das tertiäre Kondensationsprodukt ist naeh dieser Zeit gebildet. Es wird mit Na triumelilorid abgeschieden und getrocknet.
<B> Additional patent </B> to main patent no. 217241. Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1 mole of cyanuric chloride, 1 mole of the product obtained by reducing the acylation product from 1-amino-4- (4'-amino- 3'-sulfo)
-anilidoanthraquinone-2-sulfonic acid and 1 mole of p-nitrobenzoyl chloride, 1 mole of 4-amino-2-methyl-4'-oxy-1,1'-azobenzene-3'-sulfo-5'-carboxylic acid and 1 mole 1-Amino-4-oxybenzene-3-carboxylic acid can act on each other.
The new dye is a dark powder that dissolves in water with a green color and colors cotton in a weakly alkaline bath in the presence of copper sulfate and acidic sodium in washable and lightfast green tones.
Example: 48.9 parts by weight of 1-amino-4- (4'-amino-3 '- sulfo) - anilidoanthraquinone - 2 - sulfonic acid are dissolved as disodium salt in 500 parts by weight of water with the addition of 8.4 parts by weight of sodium bicarbonate. This solution is treated at about 60 with 18.5 parts by weight of 4-nitrobenzoyl chloride to which 10 parts by weight of acetone have been added.
The resulting nitrobenzoyl product is reduced with 42 parts by weight of crystallized sodium sulfide, which were dissolved in 100 parts by weight of water, at 6-0 to 70 to the corresponding aminobenzoyl product. 6.0,
8 parts by weight of the separated reduction product are added as a neutral solution in 1000 parts by weight of water to a suspension of 1.8.5 parts by weight of cyanuric chloride in 500 parts by weight of cold water. The temperature is kept at 10-15 for 1 hour. The hydrochloric acid formed during the condensation is neutralized with the appropriate amount of sodium carbonate.
Thereafter, 35.1 parts by weight of 4-amino-12-methyl-4'-oxy -1,1'-azobenzene-3'-sulfo-5'-carboxylic acid dissolved in 1000 parts by weight of warm water are added to the monocondensation product.
The temperature is increased to 40. After 24 hours, 15 parts by weight of 1-amino-1-oxybenzene-3-carboxylic acid are added and the temperature is maintained at <B> 80 'during the bleaching time. </B> The tertiary condensation product is formed near this time. It is deposited with sodium chloride and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH220651T | 1940-07-09 | ||
| CH217241T | 1940-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH220651A true CH220651A (en) | 1942-04-15 |
Family
ID=25725994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH220651D CH220651A (en) | 1940-07-09 | 1940-07-09 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH220651A (en) |
-
1940
- 1940-07-09 CH CH220651D patent/CH220651A/en unknown
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