CH216596A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH216596A CH216596A CH216596DA CH216596A CH 216596 A CH216596 A CH 216596A CH 216596D A CH216596D A CH 216596DA CH 216596 A CH216596 A CH 216596A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- sulfuric acid
- dye
- concentrated sulfuric
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 241001284352 Terminalia buceras Species 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- -1 anthraquinonyl - Chemical class 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000007962 benzene acetonitriles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/26—Carbazoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 214180. Verfahren zur Herstellung eines Nüpenfarbstof%s. Es wurde gefunden, dass ein wertvoller liüpenfarbstoff hergestellt werden kann, wenn man Di-(4'-benzoyla@mino-1'-.anthrachi- nony 1-)aminodinaphthylenthiophen, das durch Dibromieren von Dinaphthylenthiophen und Ersatz dc-r Bromatome durch 1-Amino-4- benzoylaminoanthra,chinonreste erhältlich ist,
mit kondensierenden Mitteln behandelt.
Der Farbstoff bildet ein schwarzes Pul ver, das sich mit violetter Farbe in konzen trierter Schwefelsäume löst und Baumwolle aus blaugrüner liüpe in echten, schwarz oliven Tönen färbt.
Das dem vorliegenden Verfahren als Aus- ,angsprodukt dienende Di-(4'-benzoylamino- 1' - anthrachinonyl - ) amirrodinaphthylentIiio- phen kann wie folgt hergestellt werden:
2,45 Teile Dibromdinapllthylenthiophen, hergestellt durch Bromieren von Dinaph- thylenthiophen in Nitrobenzol bei 80-70 , 3,7 Teile 1-Amino-4-benzo3@1aminoanthrachi- non, 1.,5 Teile wasserfreies LNatriumcarbonat, 1,5 Teile entwässertes Natriumacetat und 0,
15 Teile Kupferehlorür werden in 72 Tei len Nitrobenzol verteilt und 61i2 Stunden im Sieden gehalten. Nun wird heiss filtriert, der Rückstand mit Nitrobenzol, Benzol und Al kohol gewaschen und zur Reinigung mit ver dünnter Salzsäure ausgekocht, filtriert, ge waschen und getrocknet. Man erhält in sehr guter Ausbeute ein schwarzes Pulver, das sich in konzentrierter Schwefelsäure mit an fänglich grüner Farbe löst und einen Schmelz punkt über 400 besitzt.
Als kondensierende Mittel kommen insbe sondere diejenigen in Betracht, die zur Fler- stellung von Rixibschlüssen, wie Carbazol- rings.ehlüssen, geeignet sind, wie Aluminium chlorid, gegebenenfalls zusammen mit AlkaIi- haloceniden, Benzylcyaniden und Säure chloriden, hauptsächlich aber konzentrierte Schwefelsäure sowie ihre Abkömmlinge, wie Chlorsulfonsäure.
<I>Beispiel:</I> 8 Teile des Umsetzunbs-pro,duktes aus 1 Mo1 Dibromdinaphthylenthiophen mit 2 Mol 1-Amino-4-benzoylaminoantliracliinon werden in 65 Teile 96 ö ige Schwefelsäure eingetra gen und 16 Standen bei 0-5 gerührt. Dann gibt man bei dieser Temperatur in Portionen 0,6 Teile Chromsäureanhydrid zu und rührt ,weitere 4 Stunden bei 0-5 . Nun trägt man in Eis ein, filtriert ab und trocknet oder ver- pastet.
Additional patent to main patent no. 214180. Process for the production of a nub dye% see It has been found that a valuable Liüpen dye can be produced if di- (4'-benzoyla @ mino-1 '-. Anthraquinony 1-) aminodinaphthylenethiophene, which is obtained by dibrominating dinaphthylenethiophene and replacing dc-r bromine atoms with 1- Amino-4-benzoylaminoanthra, quinone residues is available,
treated with condensing agents.
The dye forms a black powder that dissolves in concentrated sulfur fringes with a violet color and dyes cotton from blue-green liüpe in real, black-olive tones.
The di- (4'-benzoylamino- 1 '- anthraquinonyl -) amirrodinaphthylenethylenephen serving as the starting product for the present process can be prepared as follows:
2.45 parts of dibromodinapllthylenethiophene, prepared by brominating dinaphthylenethiophene in nitrobenzene at 80-70, 3.7 parts of 1-amino-4-benzo3 @ 1 aminoanthraquinone, 1., 5 parts of anhydrous sodium carbonate, 1.5 parts of dehydrated sodium acetate and 0,
15 parts of copper chloride are distributed in 72 parts of nitrobenzene and kept at the boil for 61/2 hours. It is then filtered hot, the residue is washed with nitrobenzene, benzene and alcohol and, for cleaning, boiled with dilute hydrochloric acid, filtered, washed and dried. A black powder is obtained in very good yield, which dissolves in concentrated sulfuric acid with a green color and has a melting point of over 400.
Particularly suitable condensing agents are those which are suitable for the production of connections such as carbazole rings, such as aluminum chloride, optionally together with alkali halocenides, benzyl cyanides and acid chlorides, but mainly concentrated sulfuric acid and theirs Derivatives such as chlorosulfonic acid.
<I> Example: </I> 8 parts of the conversion product from 1 mol of dibromodinaphthylenethiophene with 2 mol of 1-amino-4-benzoylaminoantliracliinone are introduced into 65 parts of 96% sulfuric acid and 16 levels are stirred at 0-5. Then 0.6 part of chromic anhydride is added in portions at this temperature and the mixture is stirred for a further 4 hours at 0-5. Now it is put into ice, filtered off and dried or pasted.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH216596T | 1939-04-15 | ||
| CH214180T | 1939-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH216596A true CH216596A (en) | 1941-08-31 |
Family
ID=25725561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH216596D CH216596A (en) | 1939-04-15 | 1939-04-15 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH216596A (en) |
-
1939
- 1939-04-15 CH CH216596D patent/CH216596A/en unknown
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