CH186748A - Process for the production of an indigoid dye. - Google Patents
Process for the production of an indigoid dye.Info
- Publication number
- CH186748A CH186748A CH186748DA CH186748A CH 186748 A CH186748 A CH 186748A CH 186748D A CH186748D A CH 186748DA CH 186748 A CH186748 A CH 186748A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- blue
- green
- indigoid dye
- production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 14
- 229920000742 Cotton Polymers 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 for example Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000005406 washing 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
- C09B7/00—Indigoid dyes
- C09B7/08—Other indole-indigos
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paper (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. <B>184883.</B> Verfahren zur Herstellung eines indigolden Farbstoffes. Es wurde gefunden, dass man einen zwei Chloratome enthaltenden indigoiden Farb stoff herstellen kann, wenn man den Farb stoff der Formel
EMI0001.0005
mit chlorierenden Mitteln behandelt.
Der erhaltene, zwei Chloratome enthal tende indigoide Farbstoff stellt ein blaues Pulver dar, das sieh in konzentrierter Schwe felsäure mit grüner Farbe löst und Baum wolle aus orangegelber Küpe in blaugrünen Tönen von guter Naehtfarbe färbt. Der Farb stoff eignet sieh insbesondere für den Baum- wolldruck und gibt dabei sehr echte, blau grüne Farbtöne.
Die Behandlung mit chlorierenden Mit teln, wie zum Beispiel Chlor oder Sulfuryl- chlorid, kann vorteilhaft in Gegenwart eines indifferenten Lösungs- bezw. Suspensions- mittels, wie beispielsweise Benzol, Chlorben zol, durehgeführt werden; ferner kann auch in Gegenwart eines Halogenüberträgers chlo riert werden.
Besonders gute Resultate in bezug auf die Farbstoffausbeute werden bei Verwendung von Sulfuryleblorid als chlorie- rendes Mittel erhalten.
Be4iel: 34,7 Teile des durch Kondensation in Benzol aus dem 4-Methyl-7-methoxyisatin-a- chlorid mit 5-Methoxy-l-oxynaplithalin er haltenen Farbstoffes werden in<B>500</B> Teilen Chlorbenzol suspendiert und unter Rühren bei<B>0</B> bis<B>5 '</B> mit 2 Teilen Antimonpentachlo- rid und hierauf mit<B>31,6</B> Teilen Sulfuryl- chlorid versetzt.
Die Chlorierung, die beim langsamen Steigern der Temperatur auf etwa<B>50 '</B> einsetzt, wird durch einstündiges Rühren bei<B>60 '</B> durchgeführt und 'hierauf durch einstündiges Erhitzen auf<B>115</B> bis 120<B>'</B> beendet. Nach dem Erkalten wird der Farbstoff durch Filtrieren und Waschen mit Clilorbenzol sowie mit Alkohol isoliert.
Additional patent to the main patent no. <B> 184883. </B> Process for the production of an indigolden dye. It has been found that one can produce an indigoid dye containing two chlorine atoms if one uses the dye of the formula
EMI0001.0005
treated with chlorinating agents.
The indigoid dye obtained, containing two chlorine atoms, is a blue powder that dissolves in concentrated sulfuric acid with a green color and dyes cotton from an orange-yellow vat in blue-green shades of good sewing color. The dye is particularly suitable for cotton printing and gives very real, blue-green colors.
Treatment with chlorinating agents, such as chlorine or sulfuryl chloride, can advantageously be carried out in the presence of an inert solution or. Suspending agents, such as, for example, benzene or chlorobenzene, are carried out; can also be chlorinated in the presence of a halogen carrier.
Particularly good results with regard to the dye yield are obtained when using sulfuryl chloride as the chlorinating agent.
Example: 34.7 parts of the dye obtained by condensation in benzene from 4-methyl-7-methoxyisatin-a-chloride with 5-methoxy-l-oxynaplithalin are suspended in 500 parts of chlorobenzene and added Stir at <B> 0 </B> to <B> 5 '</B> with 2 parts of antimony pentachloride and then with <B> 31.6 </B> parts of sulfuryl chloride.
The chlorination, which begins when the temperature slowly rises to about <B> 50 '</B>, is carried out by stirring for one hour at <B> 60' </B> and then by heating to <B> 115 </ B> to 120 <B> '</B> finished. After cooling, the dye is isolated by filtering and washing with clilobenzene and with alcohol.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH186748T | 1935-07-15 | ||
| CH184883T | 1935-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH186748A true CH186748A (en) | 1936-09-30 |
Family
ID=25721117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH186748D CH186748A (en) | 1935-07-15 | 1935-07-15 | Process for the production of an indigoid dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH186748A (en) |
-
1935
- 1935-07-15 CH CH186748D patent/CH186748A/en unknown
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