CH298884A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH298884A CH298884A CH298884DA CH298884A CH 298884 A CH298884 A CH 298884A CH 298884D A CH298884D A CH 298884DA CH 298884 A CH298884 A CH 298884A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminophenyl
- dye
- purple
- reducing agent
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- -1 nitroazo Chemical group 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- CIQWSXLSSTYHKB-UHFFFAOYSA-N 2-(4-aminophenyl)-6-methyl-3h-1,3-benzothiazole-2-sulfonic acid Chemical class S1C2=CC(C)=CC=C2NC1(S(O)(=O)=O)C1=CC=C(N)C=C1 CIQWSXLSSTYHKB-UHFFFAOYSA-N 0.000 description 1
- ILMAEOWQJKHLDQ-UHFFFAOYSA-N 4-(6-ethyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(CC)=CC=C2N=C1C1=CC=C(N)C=C1 ILMAEOWQJKHLDQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011780 sodium chloride 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
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
- C09B43/10—Preparation of azo dyes from other azo compounds by reduction with formation of a new azo or an azoxy bridge
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Azofarbstoff gelangt, wenn man dianotierte 5-Nitro-2-aminobenzoesäure in alka lischem Medium mit der 2-[4'-(8"-Oxynaph- thyl- [2"] -aminophenyl) ] -6-methylbenzthiazol- X,6"-disulfonsäure,
in welcher die in X-Stel- lung befindliche Sulfonsäuregruppe dieselbe Stellung einnimmt wie die Sulfonsäuregruppe der durch Sulfonieren von 2-(4'-Aminophenyl)- 6-inetliylbenzthiazol mittels konzentrierter Schwefelsäure erhältlichen 2-(4'-Aminophenyl)- 6-methylbenzthiazolsuLlfonsälire,
kuppelt und den erhaltenen Nitroazofarbstoff mit einem milden Reduktionsmittel unter Verkettung zweier Farbstoffmoleküle reduziert.
Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit violettbrauner Farbe löst und Baumwolle oder Fasern aus regenerierter Cellulose nach dem ein- oder zweibadigen Nachkupferungsverfahren in ech ten, violettbraunen Tönen färbt.
Als mildes Reduktionsmittel wird zweck mässig Glucose in Alkalihydroxydlösung ver wendet. <I>Beispiel:</I> 18,2 Teile 5-Nitro-2-aminobenzoesäLlre wer den in bekannter Weise dianotiert. Anderseits werden 55 Teile 2-[4'-(8"-Oxynaphthyl-[2"]- aminophenyl) ] - 6 -methylbenzthiazol-X,
6"- di- sulfönsäure in 200 Teilen Wasser -unter Zu satt von 50 Teilen einer 30n/oigen Ammonium hydroxydlösung gelöst und bei 0 die diazo- tierte 5 -Nitro - 2 - aminobenzoesäure zu dieser Lösung unter Rühren zugegeben.
Nach 4stündigem Rühren wird das Volu men der Kupphtngslösung auf 4000 Teile ge stellt, auf 60 erwärmt und 17 Teile Trauben- zucker und 35 Teile einer 30 % igen Natrium- hydroxydlösung zugesetzt und 30 Minuten bei 60 gerührt.
Nun werden zur Abscheidung des gebildeten Farbstoffes 400 Teile Natri-nn- chlorid zur Lösung gegeben und nach 2stündi- gem Rühren abfiltriert. Der Filtrierrückstand wird zur Reinigung nochmals aus 300.0 Teilen heissem Wasser umgelöst, erneut abfiltriert und getrocknet.
Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if dianotated 5-nitro-2-aminobenzoic acid in an alkaline medium with the 2- [4 '- (8 "-oxynaphthyl- [2"] -aminophenyl)] -6-methylbenzthiazol- X, 6 "-disulfonic acid,
in which the sulfonic acid group in the X position occupies the same position as the sulfonic acid group of the 2- (4'-aminophenyl) -6-methylbenzthiazole sulfonates obtainable by sulfonating 2- (4'-aminophenyl) - 6-ethylbenzothiazole using concentrated sulfuric acid,
couples and reduces the nitroazo dye obtained with a mild reducing agent with a linkage of two dye molecules.
The new dye forms a dark powder that dissolves in water with a purple-brown color and colors cotton or fibers made from regenerated cellulose in real, purple-brown shades using the one- or two-bath post-copper plating process.
As a mild reducing agent, glucose in an alkali hydroxide solution is expediently used. <I> Example: </I> 18.2 parts of 5-nitro-2-aminobenzoesaelre are dianotated in a known manner. On the other hand, 55 parts of 2- [4 '- (8 "-oxynaphthyl- [2"] - aminophenyl)] - 6 -methylbenzthiazol-X,
6 "- disulfonic acid in 200 parts of water - dissolved in addition to 50 parts of a 30% ammonium hydroxide solution and at 0 the diazotized 5-nitro - 2 - aminobenzoic acid was added to this solution with stirring.
After stirring for 4 hours, the volume of the copper solution is adjusted to 4000 parts, heated to 60, 17 parts of grape sugar and 35 parts of a 30% sodium hydroxide solution are added and the mixture is stirred at 60 for 30 minutes.
In order to separate the dye formed, 400 parts of sodium chloride are now added to the solution and, after stirring for 2 hours, it is filtered off. For purification, the filter residue is redissolved from 300.0 parts of hot water, filtered off again and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH298884T | 1950-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH298884A true CH298884A (en) | 1954-05-31 |
Family
ID=4490114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH298884D CH298884A (en) | 1950-08-11 | 1950-08-11 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH298884A (en) |
-
1950
- 1950-08-11 CH CH298884D patent/CH298884A/en unknown
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