CH261868A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH261868A CH261868A CH261868DA CH261868A CH 261868 A CH261868 A CH 261868A CH 261868D A CH261868D A CH 261868DA CH 261868 A CH261868 A CH 261868A
- Authority
- CH
- Switzerland
- Prior art keywords
- aluminum chloride
- melt
- production
- vat dye
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- -1 aluminum chloride-sodium chloride Chemical compound 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims 1
- OLHYBANWJHBMLO-UHFFFAOYSA-K pyridine;trichloroalumane Chemical compound [Al+3].[Cl-].[Cl-].[Cl-].C1=CC=NC=C1 OLHYBANWJHBMLO-UHFFFAOYSA-K 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- OTKLJHUTFZDDFF-UHFFFAOYSA-N n-(8-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=12C(=O)C=3C(N)=CC=CC=3C(=O)C2=CC=CC=1NC(=O)C1=CC=CC=C1 OTKLJHUTFZDDFF-UHFFFAOYSA-N 0.000 description 2
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 description 1
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical class O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/04—Pyrazolanthrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 256236. Verfahren zur Herstellung eines Küpenfarbstoges. Es wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man die Verbindung der Formel
EMI0001.0003
mit kondensierenden Mitteln vom Typus des Aluminiumchlorids behandelt.
Der neue Farbstoff stellt ein dunkles Pul ver dar, das sich in konzentrierter Schwefel säure mit graublauer Farbe löst. Er färbt Baumwolle aus der roten alkalischen Hydro- sulfitlösung in orangen Tönen von grosser Reinheit und ausgezeichneten Echtheitseigen schaften.
Die dem vorliegenden Verfahren als Aus gangsstoff dienende Verbindung der obigen Formel kann zum Beispiel durch mehrstün diges Erhitzen äquimolekularer Mengen von 1-Amino-8-benzoylamino-anthrachinon und 5- Chlor-N-äthyl-1,9-pyrazolanthron (F. 152 bis 1540) in Naphthalin unter Zugabe von bei Anthrimid-Herstellungen üblichen Kondensa- tionsmitteln erhalten werden. Es schmilzt bei 328 bis 3300 und löst sich in konzentrierter Schwefelsäure mit grüner Farbe.
Als kondensierende Mittel vom Typus des Aluminiumchlorids können gemäss vorliegen dem Verfahren die bekannten Kombinationen von Aluminiumchlorid mit Verdünnungs- bzw. Flussmitteln verwendet werden, so Mi schungen mit Natriumchlorid, mit Pyridin oder andern tertiären Basen bzw. deren Chlor hydraten, Additionsverbindungen des Alumi niumchlorids mit Schwefeldioxyd, gegebenen falls in Mischung mit Natriumchlorid u. a. m.
<I>Beispiel:</I> In eine dünne homogene Schmelze, die aus einer Mischung von 75 Teilen trockenem, ge- pulvertem Aluminiumchlorid und 15 Teilen trockenem, gepulvertem Natrinmchlorid durch Darüberleiten von getrocknetem S0.-Gas er halten wurde, werden. bei 800 12 Teile des Kondensationsproduktes aus 5-Chlor-N-äthyl- 1.,9-py razolanthron und 1-Amino-8-benzoyl- amino-anthrachinon eingetragen. Man rührt unter Fortdauer des S0,#-Einleitens noch eine Stunde bei 100 bis 1100.
Alsdann wird die flüssige Schmelze auf eine Mischung von 1000 Teilen Wasser und 270 Teilen Natronlauge von 360 Be ausgerührt. Die warm gewordene Suspension wird aufgekocht, mit Salzsäure kongosauer gestellt und abgesaugt. Der Rück stand wird gewaschen, mit 1000 Teilen 10 % iger Salzsäure ausgekocht, abgesaugt, neutral gewaschen und getrocknet. Sofern rotwendig, kann er noch durch Timküpen ge reinigt werden.
<B> Additional patent </B> to main patent no. 256236. Process for producing a vat dye. It has been found that a valuable vat dye can be made using the compound of the formula
EMI0001.0003
treated with condensing agents of the aluminum chloride type.
The new dye is a dark powder that dissolves in concentrated sulfuric acid with a gray-blue color. It dyes cotton from the red alkaline hydrosulfite solution in orange tones of great purity and excellent fastness properties.
The present process as a starting compound of the above formula can be prepared, for example, by several hours of heating equimolecular amounts of 1-amino-8-benzoylamino-anthraquinone and 5-chloro-N-ethyl-1,9-pyrazolanthrone (F. 152 to 1540) in naphthalene with the addition of condensing agents customary in anthrimide production. It melts at 328 to 3300 and dissolves in concentrated sulfuric acid with a green color.
The known combinations of aluminum chloride with diluents or fluxes can be used as condensing agents of the aluminum chloride type according to the present process, such as mixtures with sodium chloride, with pyridine or other tertiary bases or their chlorine hydrates, addition compounds of aluminum chloride with sulfur dioxide , if necessary in a mixture with sodium chloride u. a. m.
<I> Example: </I> In a thin homogeneous melt, which was obtained from a mixture of 75 parts of dry, powdered aluminum chloride and 15 parts of dry, powdered sodium chloride by passing dried SO gas over it. entered at 800 12 parts of the condensation product of 5-chloro-N-ethyl- 1., 9-py razolanthron and 1-amino-8-benzoylamino-anthraquinone. The mixture is stirred for another hour at 100 to 1100 while continuing to introduce S0, #.
The liquid melt is then stirred into a mixture of 1000 parts of water and 270 parts of 360 Be sodium hydroxide solution. The suspension that has become warm is boiled, acidified to Congo with hydrochloric acid and filtered off with suction. The residue is washed, boiled with 1000 parts of 10% hydrochloric acid, filtered off with suction, washed neutral and dried. If necessary, it can still be cleaned with Timküpen.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261868T | 1946-02-01 | ||
| CH256236T | 1947-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261868A true CH261868A (en) | 1949-05-31 |
Family
ID=25729965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261868D CH261868A (en) | 1946-02-01 | 1946-02-01 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261868A (en) |
-
1946
- 1946-02-01 CH CH261868D patent/CH261868A/en unknown
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