AT46865B - Process for the preparation of halogenated red thioindigo dyes. - Google Patents
Process for the preparation of halogenated red thioindigo dyes.Info
- Publication number
- AT46865B AT46865B AT46865DA AT46865B AT 46865 B AT46865 B AT 46865B AT 46865D A AT46865D A AT 46865DA AT 46865 B AT46865 B AT 46865B
- Authority
- AT
- Austria
- Prior art keywords
- halogenated
- red
- preparation
- thioindigo dyes
- dyes
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 6
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung halogenierter roter Thioindigofarbstoffe.
EMI1.1
wertvollen, halogenierten Farbstoffen gelangt.
Dieses ist in mehrfacher Hinsicht überraschend : Es war weder zu erwarten, dass sich die Alkoxylgruppen bei der Halogenierung indifferent verhalten würden (und bei stärkerer halogenierung, z. B. bei höherer Temperatur tritt auch tatsächlich eine Zersetzung ein) noch war zu erwarten, dass man auf diesem Wege zu rein roten Farbstoffen gelangen würde.
Beispiel I: 1 Teil 6.61-Diäthoxythioindigo C2H5O:S-C-4:2:1 wird mit 3 Teilen Brom unter Abkühlung vorrührt. Man lässt einige Zeit stehen, verdünnt die pulverige
EMI1.2
stoff usw. angewandt werden, wobei sich die vorbeschriebene schwärzliche Masse nicht bildet, vielmehr sich direkt das Bromierungsprodukt als solches ausscheidet, ferner kann man auch je nach dem gewünschten Bromierungsgrade schwach erwärmen.
Beispiel II: 1 Teil 6.61-Diäthoxythioindigo wird mit 4 Teilen Sulfurylchlorid verrührt und einige Zeit stehen gelassen ; man kann hierbei auch Lösungsmittel, wie Nitrobenzol, Tetrachlorkohlenstoff, zusetzen. Auch kann man bei der Umsetzung je nach
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masse mit Tetrachlorkohlenstoff, saugt ab und wäscht das Produkt mit Alkohol.
Der so Prhi11teno Farbstoff löst sich in konzentrierter Schwefelsäure mit tief blauer
EMI1.4
Ähnliche Farbstoffe werden beim Behandeln mit Chlorgas erhalten.
An Stelle des 6.61-Diäthoxythioindigos lassen sich auch dessen Loukoverbindung,
EMI1.5
wenden.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of halogenated red thioindigo dyes.
EMI1.1
valuable, halogenated dyes.
This is surprising in several respects: it was neither to be expected that the alkoxyl groups would behave indifferently during halogenation (and in the case of stronger halogenation, e.g. at a higher temperature, decomposition actually occurs) nor was it to be expected that this would lead to pure red dyes.
Example I: 1 part of 6.61-diethoxythioindigo C2H50: S-C-4: 2: 1 is pre-stirred with 3 parts of bromine while cooling. Let stand for some time, dilute the powdery
EMI1.2
substance, etc. are used, whereby the blackish mass described above does not form, rather the bromination product as such is precipitated directly; furthermore, depending on the desired degree of bromination, it is also possible to heat gently.
Example II: 1 part of 6.61 diethoxythioindigo is stirred with 4 parts of sulfuryl chloride and left to stand for some time; you can also add solvents such as nitrobenzene or carbon tetrachloride. Also you can depending on the implementation
EMI1.3
mass with carbon tetrachloride, vacuum and wash the product with alcohol.
The so Prhi11teno dye dissolves in concentrated sulfuric acid with a deep blue color
EMI1.4
Similar dyes are obtained on treatment with chlorine gas.
Instead of the 6.61 diethoxythioindigo, its Louko compound,
EMI1.5
turn.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1907213465D DE213465C (en) | 1907-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT46865B true AT46865B (en) | 1911-03-10 |
Family
ID=5813368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT46865D AT46865B (en) | 1907-10-23 | 1909-03-24 | Process for the preparation of halogenated red thioindigo dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT46865B (en) |
-
1909
- 1909-03-24 AT AT46865D patent/AT46865B/en active
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