CH249377A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH249377A CH249377A CH249377DA CH249377A CH 249377 A CH249377 A CH 249377A CH 249377D A CH249377D A CH 249377DA CH 249377 A CH249377 A CH 249377A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- benzanthrone
- bzl
- production
- brown
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 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 claims description 3
- PXNNPGGYHAWDJW-UHFFFAOYSA-N N-(4-amino-9,10-dioxo-1-anthracenyl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC=C1 PXNNPGGYHAWDJW-UHFFFAOYSA-N 0.000 claims description 3
- 229920002955 Art silk Polymers 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent 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
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
- C09B1/43—Dicarboxylic acids
-
- 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
- C09B3/06—Preparation from starting materials already containing the benzanthrone nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man ein funktionelles Derivat der Benzanthron-6,Bzl-dicarbonsäure mit 2 Mol 1-Amino-4-benzoylaminoanthrachinon um setzt.
Der neue Farbstoff ist ein braunes Pulver, das sich in konz. Schwefelsäure mit roter Farbe löst und Baumwolle sowie Kunstseide aus regenerierter Zellulose aus violettbrauner Küpe in echten orangebraunen Tönen färbt.
Die gemäss, vorliegendem Verfahren als Ausgangsprodukt verwendete Benzanthron- 6,Bzl-dicarbonsäure kann durch alkalische oder saure Verseifung von 6,Bz1-Dicyanbenz- anthron (siehe D. R. P. Nr. 467118, Beispiel 3) erhalten werden. Als funktionelle Derivate, die mit der Aminkomponente zur Reaktion gebracht werden sollen, sind insbesondere die Säurehalogenide, z. B. das Säurechlorid, zu erwähnen. Diese können aus der Säure in be kannter Weise erhalten werden.
Die Um setzung der Säurederivate mit der Amin komponente wird vorteilhaft durch Erhitzen in Lösungsmitteln, vorteilhaft solchen von relativ hohem Siedepunkt, z. B. Di- oder Trichlorbenzol, Nitrobenzol, Naphthalin oder Chlornaphthalin, durchgeführt.
Beispiel: 15,9 Teile Benzanthron-6,Bz1-diearbon- säure werden durch Erhitzen mit 20 Teilen Thionylchlorid in 1000 Teilen trockenem o-Dichlorbenzol in das Säurechlorid verwan delt. Nach dem Abdes.tillieren des -unver- brauchten Thionylchlorides trägt man bei 150 34,2 Teile 1-Amino-4-benzoylamino- anthrachinon ein.
Nach zweistündigem Rüh ren bei 150 ist die Farbstoffbildung beendet. Man saugt in der Wärme ab, wäscht mit o-Dichlorbenzol und Alkohol aus und trocknet.
Process for the production of a vat dye. It has been found that a valuable vat dye can be produced if a functional derivative of benzanthrone-6, Bzl-dicarboxylic acid is reacted with 2 moles of 1-amino-4-benzoylaminoanthraquinone.
The new dye is a brown powder that is in conc. Sulfuric acid dissolves red and dyes cotton and artificial silk from regenerated cellulose from a purple-brown vat in real orange-brown tones.
The benzanthrone-6, Bzl-dicarboxylic acid used as the starting product according to the present process can be obtained by alkaline or acidic saponification of 6, Bz1-dicyanobenzanthrone (see D. R. P. No. 467118, Example 3). As functional derivatives that are to be reacted with the amine component, the acid halides, eg. B. the acid chloride to mention. These can be obtained from the acid in a known manner.
The implementation of the acid derivatives with the amine component is advantageous by heating in solvents, advantageously those of a relatively high boiling point, eg. B. di- or trichlorobenzene, nitrobenzene, naphthalene or chloronaphthalene carried out.
Example: 15.9 parts of benzanthrone-6, Bz1-diacid are converted into the acid chloride by heating with 20 parts of thionyl chloride in 1000 parts of dry o-dichlorobenzene. After the unused thionyl chloride has been removed, 34.2 parts of 1-amino-4-benzoylamino-anthraquinone are entered at 150.
After two hours of stirring at 150, the dye formation is complete. It is suctioned off in the heat, washed with o-dichlorobenzene and alcohol and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH249377T | 1946-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH249377A true CH249377A (en) | 1947-06-30 |
Family
ID=4467499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH249377D CH249377A (en) | 1946-07-04 | 1945-07-27 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH249377A (en) |
-
1945
- 1945-07-27 CH CH249377D patent/CH249377A/en unknown
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