CH204130A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH204130A CH204130A CH204130DA CH204130A CH 204130 A CH204130 A CH 204130A CH 204130D A CH204130D A CH 204130DA CH 204130 A CH204130 A CH 204130A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- dye
- vat
- vat dye
- azobenzene
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 5
- 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 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CAFWWZWJFFJXTF-UHFFFAOYSA-N methyl 4-nitrosobenzoate Chemical compound COC(=O)C1=CC=C(N=O)C=C1 CAFWWZWJFFJXTF-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 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
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
- C09B43/36—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines with amino-anthracene or amino-anthraquinone dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Vorliegendes Patent bezieht sich auf ein Verfahren zur Herstellung eines Küpenfarb- stoffes, dadurch gekennzeichnet, dass man ein funktionelles Derivat der Azobenzol-4, 3', 5'- triearbonsäure mit 1-Amino-5-benzoylamino- anthrachinon im Molekularverhältnis 1:3 kon densiert.
Der so erhaltene Farbstoff löst sich in konzentrierter Schwefelsäure mit braunroter Farbe und färbt Baumwolle aus rotvioletter Küpe in gelben Tönen. Die Färbungen wei sen ausgezeichnete Echtheitseigenschaften auf. <I>Beispiel;</I> 103 Teile 1-Amino-5-benzoyla,minoantbra- chinon werden in etwa 700 Teilen o-Dichlor- benzol bei 160 C gelöst, dann gibt man 37 Teile Azobenzol-4, 3', 5'-tricarbonsäuretri- ehlorid (Schmelzpunkt 135 C) zu und rührt etwa zwei Stunden bei dieser Temperatur.
Der mit vorzüglicher Ausbeute gebildete Farb stoff wird abgesaugt, gewaschen und getrock net.
Das angewandte Azobenzol-4, 3', 5'-tri- carbonsäuretrichlorid kann aus Azobenzol-4, 3', 5'-tricarbonsäure mit Phosphorpentachlo- rid in Monochlorbenzol hergestellt werden. Die Tricarbonsäure selbst kann beispielsweise durch Kondensation von p-Nitrosobenzoesäure- methylester mit 5-Aminoisophthalsäure in Eis essig und anschliessende alkalische yerseifung gewonnen werden.
Process for the production of a vat dye. The present patent relates to a process for the production of a vat dye, characterized in that a functional derivative of azobenzene-4, 3 ', 5'-triearboxylic acid is mixed with 1-amino-5-benzoylamino-anthraquinone in a molecular ratio of 1: 3 condensed.
The dye obtained in this way dissolves in concentrated sulfuric acid with a brownish-red color and dyes cotton from a red-violet vat in yellow tones. The dyeings have excellent fastness properties. <I> Example; </I> 103 parts of 1-amino-5-benzoyla, minoantbraquinone are dissolved in about 700 parts of o-dichlorobenzene at 160 ° C., then 37 parts of azobenzene-4, 3 ', 5 are added '-tricarboxylic acid trichloride (melting point 135 ° C.) and stirred for about two hours at this temperature.
The dye formed with excellent yield is filtered off with suction, washed and net getrock.
The azobenzene-4, 3 ', 5'-tricarboxylic acid trichloride used can be prepared from azobenzene-4, 3', 5'-tricarboxylic acid with phosphorus pentachloride in monochlorobenzene. The tricarboxylic acid itself can be obtained, for example, by condensation of methyl p-nitrosobenzoate with 5-aminoisophthalic acid in glacial acetic acid and subsequent alkaline hydrolysis.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE204130X | 1936-12-03 | ||
| CH200369T | 1938-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204130A true CH204130A (en) | 1939-04-15 |
Family
ID=25723476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204130D CH204130A (en) | 1936-12-03 | 1937-11-26 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204130A (en) |
-
1937
- 1937-11-26 CH CH204130D patent/CH204130A/en unknown
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