CH180408A - Process for the preparation of a substantive azo dye. - Google Patents
Process for the preparation of a substantive azo dye.Info
- Publication number
- CH180408A CH180408A CH180408DA CH180408A CH 180408 A CH180408 A CH 180408A CH 180408D A CH180408D A CH 180408DA CH 180408 A CH180408 A CH 180408A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- violet
- acid
- preparation
- azo dye
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 6
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 3
- 150000001880 copper compounds Chemical class 0.000 claims description 3
- YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- CEIXBBVHIIHZON-UHFFFAOYSA-N 2-(4-amino-3-methoxyphenyl)-6-methyl-3H-1,3-benzothiazole-2-sulfonic acid Chemical compound NC1=C(C=C(C=C1)C1(SC2=C(N1)C=CC(=C2)C)S(=O)(=O)O)OC CEIXBBVHIIHZON-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- -1 amino compound 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CCPUOOUROHGAOD-UHFFFAOYSA-N 3-methoxy-4-nitrobenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC=C1[N+]([O-])=O CCPUOOUROHGAOD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines substantiven Azofarbstoffes. Es wurde gefunden, dass man neue sub- stantive Azofarbstoffe erhält, wenn man 2-(Alkoxy- bezw. Halogen-amicioar#yl)-arylen- thiazolverbindungen der allgemeinen Formel:
EMI0001.0010
diazotiert und die erhaltenen Diazoverbin- dungen mit Kupplungskomponenten vereinigt.
Die so erhaltenen Farbstoffe sind infolge der in o-Stellung zur Azogruppe stehenden Alkoxygruppe befähigt, in Substanz oder auf der Faser Kupferverbindungen zu bilden, welche sich durch hervorragende Lichtecht heit auszeichnen.
Die als Diazokomponente verwendeten Verbindungen obiger Konstitution können auf folgende Weise erhalten werden: Man kondensiert ein 4-Nitro-3-alkoxy- oder Ha logen-arylcarbonsäurechloridmit einem Amino- aryl-o-merkaptan und reduziert das erhaltene Nitroar-yl-arylenthiazol zur entsprechenden Aminoverbindung. In diese oder in die ent sprechende Nitroverbindung können gege benenfalls noch weitere Substituenten, z. B. die Sulfogruppe, eingeführt werden.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Herstellung eines sub- stantiven Azofarbstoffes, dadurch gekenn zeichnet, dass man die Diazoverbindung der 2-(4'-Amiuo-3'-methoxyphenyl)-6-methylbenz- thiazolsulfosäure mit 2-Phenylamino-5-naph- thol-7-sulfosäure kuppelt.
Der neue Farbstoff stellt ein metallisch glänzendes- Pulver dar, welches sich in Wasser rotviolett und in konzentrierter Schwefelsäure blau löst und auf Baumwolle in schönem rotviolettem Ton zieht. Durch Überführung des Farbstoffes in seine Kupfer verbindung wird ein lebhaftes Blauviolett mit wesentlich verbesserter Lichtechtheit erhalten.
<I>Beispiel;</I> 372 kg 2-(4'-Amino-3'-methoxyphenyl)- 6-methylbenzthiazolsulfosaures Natrium (her gestellt durch Kondensation von 4-Nitro-3- methoxybenzoylchlorid mit 4-Amino-3-mer- kaptotoluol, Reduktion und Sulfierung) wer den in 3000 Liter Wasser gelöst und mit einer Lösung von 70 kg Natriumnitrit in . 350 Liter Wasser versetzt.
Die Mischung lässt mau daraufhin bei 25 C in verdünnte Salzsäure, hergestellt aus 270 kg Salzsäure vom spezifischen Gewicht 1,18 und 1800 Liter Wasser, einlaufen und rührt bis zur Beendigung der Diazotierung. Dann läuft die Diazoverbindung bei 0 C in eine Lö - sung von 350 kg 2-phenylamino-5-näphthol- 7-sulfosaurem Natrium und 318 kg Soda in 2500 Liter Wasser, der 500 kg Eis zuge geben waren. Nach beendeter Kupplung wird der Farbstoff durch Aussalzen isoliert, fil triert und getrocknet.
Process for the preparation of a substantive azo dye. It has been found that new substantial azo dyes are obtained if 2- (alkoxy or halo-amicioar # yl) -arylene thiazole compounds of the general formula are used:
EMI0001.0010
diazotized and the resulting diazo compounds combined with coupling components.
The dyes obtained in this way are, owing to the alkoxy group in the o-position to the azo group, capable of forming copper compounds in substance or on the fiber, which are characterized by excellent lightfastness.
The compounds of the above constitution used as the diazo component can be obtained in the following manner: A 4-nitro-3-alkoxy- or halogen-arylcarboxylic acid chloride is condensed with an aminoaryl-o-mercaptan and the resulting nitroar-yl-arylthiazole is reduced to the corresponding amino compound . In this or in the corresponding nitro compound can, if necessary, other substituents such. B. the sulfo group are introduced.
The present patent now relates to a process for the preparation of a substantial azo dye, characterized in that the diazo compound of 2- (4'-Amiuo-3'-methoxyphenyl) -6-methylbenzethiazolesulfonic acid with 2-phenylamino-5 -naphthol-7-sulfonic acid couples.
The new dye is a metallic, shiny powder, which dissolves in red-violet water in water and blue in concentrated sulfuric acid and has a beautiful red-violet tone on cotton. By converting the dye into its copper compound, a vivid blue-violet with significantly improved lightfastness is obtained.
<I> Example; </I> 372 kg of 2- (4'-amino-3'-methoxyphenyl) - 6-methylbenzthiazolesulfonic acid sodium (produced by condensation of 4-nitro-3-methoxybenzoyl chloride with 4-amino-3-mer - kaptotoluene, reduction and sulfation) who dissolved in 3000 liters of water and treated with a solution of 70 kg of sodium nitrite in. 350 liters of water are added.
The mixture is then poured into dilute hydrochloric acid, prepared from 270 kg hydrochloric acid with a specific weight of 1.18 and 1800 liters of water, at 25 ° C. and stirred until the diazotization is complete. The diazo compound then runs at 0 C into a solution of 350 kg of 2-phenylamino-5-naphthol-7-sulfo-acid sodium and 318 kg of soda in 2500 liters of water to which 500 kg of ice were added. After coupling has ended, the dye is isolated by salting out, filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE180408X | 1934-02-15 | ||
| DE180534X | 1934-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH180408A true CH180408A (en) | 1935-10-31 |
Family
ID=25756296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH180408D CH180408A (en) | 1934-02-15 | 1935-02-06 | Process for the preparation of a substantive azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH180408A (en) |
-
1935
- 1935-02-06 CH CH180408D patent/CH180408A/en unknown
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