CH217967A - Process for the preparation of a polyazo dye. - Google Patents
Process for the preparation of a polyazo dye.Info
- Publication number
- CH217967A CH217967A CH217967DA CH217967A CH 217967 A CH217967 A CH 217967A CH 217967D A CH217967D A CH 217967DA CH 217967 A CH217967 A CH 217967A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- mole
- dye
- weight
- parts
- Prior art date
Links
- -1 polyazo Polymers 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 5
- 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 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 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
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate 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
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
Zusatzpatent zum Hauptpatent Nr. 215147. Verfahren zur Herstellung eines Polyazofarbstoffes. Es wurde befunden, dass man einen neuen Polyazofarbstoff erhalten kann, wenn man auf 1 Mol Cyanurchlorid 1 Mol des Monoazofarbstoffes, der erhalten wird durch Reduzieren der Nitrogruppe zur Aminogruppe in dem Produkt,
das selbst erhalten wird durch Einwirkenlassen von 4-Nitrobenzoyl- cshlorid auf den Monoazofarbstoff aus diazo- tierter 5-Amino-2-oxy-l-carboxybenzol-3-sul- fonsäure und 1-Methyl-4-methoxy-3-amino- benzol, 1 Mol 4-Amino-4'-oxyazo-2-methyl- benzol-3'-carbonsäure und 1 Mol Anilin ein wirken lässt.
Der neue Polyazofarbstoff färbt Baumwolle in schwach alkalischem Bade bei Gegenwart von Kupfersulfat und weinsaurem Natrium in waschechten gelben Tönen an. <I>Beispiel:</I> 38,6 Gewichtsteile des Monoazofarbstoffes aus diazotierter 5-Amino-2-oxy-l-carboxy- benzol - 3 - sulfonsäure und 1 - Methyl - 4- methoxy-3-aminobenzol werden als Natrium salz in 500 Gewichtsteilen Wasser unter Zu- satz von 13,
5 Gewichtsteilen Natriumacetat gelöst. Diese Lösung wird bei etwa <B>60'</B> mit 18,5 Gewichtsteilen 4-Nitrobenzoylchlorid, die mit 5 Gewichtsteilen Aceton versetzt wurden, behandelt.
Man reduziert das Nitro- benzoylprodukt mit 42 Gewichtsteilen kri stallisiertem Natriumsulfid, die in 75 Ge wichtsteilen Wasser gelöst wurden, bei 65 bis 70 zum Aminobenzoylprodukt. 50 Gewichts teile des abgeschiedenen Reduktionsproduktes werden als neutrale Lösung in 1500 Ge wichtsteilen Wasser zu einer Anschlämmung von 18,4 Gewichtsteilen Cyanurchlorid in 500 Gewichtsteilen kaltem Wasser gegeben. Die bei der Kondensation entstehende Salz säure wird durch die entsprechende Menge Natriumearbonat neutralisiert.
Hernach wer den 27,8 Gewichtsteile 4-amino-4'-oxyazo-2- methylbenzol-3'-carbonsaures Natrium, das in Wasser gelöst wurde, zugefügt und die Tem peratur auf 40<B>'</B>erhöht. Nach 2 Stunden gibt man 9,3 Gewichtsteile Anilin zu und hält die Temperatur während der gleichen Zeit auf 80 . Das tertiäre Kondensationsprodukt ist nach dieser Zeit gebildet. Es wird mit Na triumchlorid abgeschieden und getrocknet.
Additional patent to main patent No. 215147. Process for the production of a polyazo dye. It has been found that a new polyazo dye can be obtained by adding, for 1 mole of cyanuric chloride, 1 mole of the monoazo dye obtained by reducing the nitro group to the amino group in the product,
this itself is obtained by allowing 4-nitrobenzoyl chloride to act on the monoazo dye from diazo-tated 5-amino-2-oxy-1-carboxybenzene-3-sulphonic acid and 1-methyl-4-methoxy-3-aminobenzene , 1 mole of 4-amino-4'-oxyazo-2-methyl-benzene-3'-carboxylic acid and 1 mole of aniline can act.
The new polyazo dye dyes cotton in a weakly alkaline bath in the presence of copper sulfate and tartrate of sodium in washfast yellow shades. <I> Example: </I> 38.6 parts by weight of the monoazo dye from diazotized 5-amino-2-oxy-1-carboxy-benzene - 3 - sulfonic acid and 1 - methyl - 4-methoxy-3-aminobenzene are salted as sodium in 500 parts by weight of water with the addition of 13,
5 parts by weight of sodium acetate dissolved. This solution is treated at about <B> 60 '</B> with 18.5 parts by weight of 4-nitrobenzoyl chloride to which 5 parts by weight of acetone have been added.
The nitrobenzoyl product is reduced with 42 parts by weight of crystallized sodium sulfide, which were dissolved in 75 parts by weight of water, at 65 to 70 to the aminobenzoyl product. 50 parts by weight of the deposited reduction product are added as a neutral solution in 1500 parts by weight of water Ge to a slurry of 18.4 parts by weight of cyanuric chloride in 500 parts by weight of cold water. The hydrochloric acid formed during the condensation is neutralized by the appropriate amount of sodium carbonate.
Thereafter, the 27.8 parts by weight of 4-amino-4'-oxyazo-2-methylbenzene-3'-carboxylic acid sodium, which was dissolved in water, was added and the temperature was increased to 40 '. After 2 hours, 9.3 parts by weight of aniline are added and the temperature is maintained at 80 for the same time. The tertiary condensation product is formed after this time. It is precipitated with sodium chloride and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215147T | 1939-07-12 | ||
| CH217967T | 1939-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217967A true CH217967A (en) | 1941-11-15 |
Family
ID=25725690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217967D CH217967A (en) | 1939-07-12 | 1939-07-12 | Process for the preparation of a polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH217967A (en) |
-
1939
- 1939-07-12 CH CH217967D patent/CH217967A/en unknown
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