CH289993A - Process for the preparation of an anthraquinone dye. - Google Patents
Process for the preparation of an anthraquinone dye.Info
- Publication number
- CH289993A CH289993A CH289993DA CH289993A CH 289993 A CH289993 A CH 289993A CH 289993D A CH289993D A CH 289993DA CH 289993 A CH289993 A CH 289993A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- amino
- preparation
- anthraquinone dye
- blue
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000001000 anthraquinone dye Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 5
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- YNHZHCDOSUFTIW-UHFFFAOYSA-N n-(3-aminophenyl)-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC(N)=C1 YNHZHCDOSUFTIW-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 1-amino-3- (methoxybenzoylamino) benzene Chemical compound 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- CWEMVGIBTDJEIT-UHFFFAOYSA-N N=C(C(C=C1Br)S(O)(=O)=O)C(C(C2=CC=CC=C22)=O)=C1C2=O Chemical compound N=C(C(C=C1Br)S(O)(=O)=O)C(C(C2=CC=CC=C22)=O)=C1C2=O CWEMVGIBTDJEIT-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000010992 reflux Methods 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
- 238000003756 stirring Methods 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
- C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonfarbstoffes. Zum Färben von Mischgeweben aus Wolle und Zellwolle benötigt man Farbstoffe, die Wolle auch aus neutralem Bade anfärben. Es sind nur wenige echte blaue saure Woll- farbstoffe bekannt, die ohne Zusatz von Säu ren auf Wolle ausreichend kräftige und echte Färbungen geben.
Es wurde nun gefunden, dass man einen neuen gut neutralziehenden blauen Farbstoff erhält, wenn man 1-Amino-4-bromanthrachi- nori-2-sulfonsäure mit 1-Amino-3-(methoxy- benzoylamino)-benzol umsetzt.
Die Herstellung dieses Amins erfolgt durch Umsetzung von m-Nitranilin mit p-lVlethoxy- benzoylchlorid und anschliessende Reduktion der erhaltenen Nitroverbindung in an sich be kannter Weise. Die Umsetzung mit der 1- :lmino-4-bromanthrachinon-2-sulfonsäure fin det in wässerigem oder alkoholisch wässerigem Medium nach bekannten Methoden statt.
Der neue Farbstoff ist in seinem neutra len Ziehvermögen den bekannten Farbstoffen überlegen.
<I>Beispiel:</I> 10 Gewichtsteile 1-amino-4-bromanthraehi- non-2-sulfonsaures Natrium, 20 Gewichtsteile 1- Amino - 3- (4'-methoxybenzoylamino) - benzol, 15 Gewichtsteile Natriumbicarbonat, 1 Ge wichtsteil Kupferchlorür werden in einem Gemisch von 160 Gewichtsteilen Wasser und 40 Gewichtsteilen Äthylalkohol unter Rühren und Rückfluss so lange gekocht, bis man an Hand von Proben festgestellt hat, dass die sich bildende blaue Lösung an Intensität und Klarheit der Nuance nicht mehr zunimmt.
Beim Abkühlen scheidet sich der gebildete Farbstoff kristallin ab. Fr wird abgesaugt und durch Lösen in Wasser, Filtrieren und Aussalzen gereinigt.
Im trockenen Zustand stellt der Farbstoff ein blaues Pulver dar, das sich in Wasser mit klar blauer Farbe löst. Wolle wird aus der neutralen Lösung in kräftigen klaren blauen Tönen angefärbt. Die Färbung ist sehr licht- und walkecht.
Process for the preparation of an anthraquinone dye. To dye blended fabrics made of wool and viscose wool you need dyes that can also be dyed from neutral baths. Only a few genuine blue, acidic wool dyes are known that give wool sufficiently strong and genuine colors without the addition of acids.
It has now been found that a new, good, neutral blue dye is obtained if 1-amino-4-bromoanthraquinone-2-sulfonic acid is reacted with 1-amino-3- (methoxybenzoylamino) benzene.
This amine is prepared by reacting m-nitroaniline with p-IVlethoxybenzoyl chloride and then reducing the nitro compound obtained in a manner known per se. The reaction with 1-: imino-4-bromoanthraquinone-2-sulfonic acid takes place in an aqueous or alcoholic aqueous medium according to known methods.
The new dye is superior to the known dyes in its neutral drawability.
<I> Example: </I> 10 parts by weight of 1-amino-4-bromanthraehinone-2-sulfonic acid sodium, 20 parts by weight of 1- amino-3- (4'-methoxybenzoylamino) benzene, 15 parts by weight of sodium bicarbonate, 1 part by weight Copper chloride is boiled in a mixture of 160 parts by weight of water and 40 parts by weight of ethyl alcohol with stirring and reflux until it has been determined on the basis of samples that the blue solution that forms no longer increases in intensity and clarity of the shade.
The dye formed separates out in crystalline form on cooling. Fr is filtered off with suction and purified by dissolving in water, filtering and salting out.
When dry, the dye is a blue powder that dissolves in water with a clear blue color. Wool is dyed from the neutral solution in strong clear blue tones. The coloring is very lightfast and whackfast.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB289993X | 1949-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH289993A true CH289993A (en) | 1953-04-15 |
Family
ID=10284634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH289993D CH289993A (en) | 1949-09-01 | 1950-08-25 | Process for the preparation of an anthraquinone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH289993A (en) |
-
1950
- 1950-08-25 CH CH289993D patent/CH289993A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH289993A (en) | Process for the preparation of an anthraquinone dye. | |
| CH209089A (en) | Process for the preparation of a water-soluble dye. | |
| DE842101C (en) | Process for the preparation of anthraquinone dyes | |
| DE540217C (en) | Process for the production of azo dyes | |
| DE536294C (en) | Process for the preparation of Kuepen dyes of the anthraquinone series | |
| CH197285A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH191165A (en) | Process for the preparation of a new monoazo dye. | |
| CH175252A (en) | Process for the preparation of an anthraquinone dye. | |
| CH175881A (en) | Process for the preparation of a substantive copper-containing azo dye. | |
| CH267274A (en) | Process for the preparation of a monoazo dye. | |
| CH261368A (en) | Process for the preparation of a monoazo dye. | |
| CH265737A (en) | Process for the preparation of a water-soluble dye of the naphthoquinone series. | |
| CH308784A (en) | Process for the preparation of a new disazo dye. | |
| CH299605A (en) | Process for the preparation of a monoazo dye. | |
| CH144494A (en) | Process for preparing a coloring reaction product obtained from a monoazo dye. | |
| CH156316A (en) | Process for the production of a chromium-containing dye. | |
| CH189316A (en) | Process for the preparation of a dioxazine dye sulfonic acid. | |
| CH308786A (en) | Process for the preparation of a new disazo dye. | |
| CH301343A (en) | Process for the preparation of a sulfonic acid amide of the anthraquinone series. | |
| CH216321A (en) | Process for the production of an acidic wool dye. | |
| CH269393A (en) | Process for the preparation of a vivid acid dye of the anthraquinone series. | |
| CH150305A (en) | Process for the preparation of an acidic disazo dye. | |
| CH153400A (en) | Process for the production of a wool dye of the anthraquinone series. | |
| CH180293A (en) | Process for the production of a new dye. | |
| CH240127A (en) | Process for the preparation of a new monoazo dye. |