CH158249A - Process for the preparation of an indigoid vat dye. - Google Patents
Process for the preparation of an indigoid vat dye.Info
- Publication number
- CH158249A CH158249A CH158249DA CH158249A CH 158249 A CH158249 A CH 158249A CH 158249D A CH158249D A CH 158249DA CH 158249 A CH158249 A CH 158249A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- oxythionaphthene
- vat dye
- preparation
- chlorine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000010411 cooking Methods 0.000 claims description 4
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004682 monohydrates Chemical class 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 1
- 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 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000243 solution Substances 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
- 239000012670 alkaline solution Substances 0.000 description 1
- AIOLRLMFOWGSPL-UHFFFAOYSA-N chembl1337820 Chemical compound C1=CC=C2C(N=NC3=C4C=CC(=CC4=CC(=C3O)S(O)(=O)=O)S(O)(=O)=O)=CC=CC2=C1 AIOLRLMFOWGSPL-UHFFFAOYSA-N 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
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- -1 potassium ferricyanide Chemical compound 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Yerfahren zur Darstellung eines indigoiden Küpenfarbstoffes. Es wurde gefunden, dass das im Schweizer patent Nr. 156434 beschriebene 4.5-Didiethyl- 7-ohlor-oxythionaphten sich in indigoide Kti- penfarbstoffe überführen lässt. Durch Behandeln mit Oxydationsmitteln lässt sich daraus der symmetrische Thioindigofarbstoff herstellen,
der einen lebhaften rotvioletten Küpenfarb- stoff von hervorragender Sodakochechtheit darstellt. Kondensiert man das 4. 5-Diniethyl- 7-ohlor-oxythionaphten mit eyklischen Dike- tonen oder deren 2-Derivaten (wie Isatinen und Naphtisatinen, deren Chloriden und Aryliden,
mit Oxythionaphtenen und Naphtoxythionaph- tenen und deren Anilen, ferner mit Acenaph- tenchinon), bezw. setzt man 4.
6-Dimethyl-7- chlor-oxythionapbten-2-anile mit Körpern um, die eine reaktionsfähige Methylengruppe ent halten, so erhält man gemischte Thioindigo- farbstoffe, die die Faser aus der Küpe in rosa roten bis blauen Tönen anfärben, die siel-i neben ihrer Lebhaftigkeit durch eine hervor ragende Sodakochechtheit auszeichnen.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Darstellung eines indigoiden Küpenfarbstoffes, dadurch gekennzeichnet, dass man 4.5-Dimethyl-7-(,blor-oxythionaphten einer oxydierenden Kondensation unterwirft.
Der so erhaltene Farbstoff ist getrocknet von bordoroter Farbe, löst sich grün in Mo nohydrat, verküpt mit Natronlauge und Hy- drosulfit hellgelb, färbt und druckt auf Baum wolle in lebhaft rotvioletten Tönen von her vorragender Kochechtheit und übertrifft in dieser Beziehung sowohl als auch in Klar heit der Nuance den koloristisch nahestehen den<B>5.</B> 5'-Dichlor-7 <B>.</B> 7'-dimethyl-thioindigo. <I>Beispiel<B>1:
</B></I> Die Kondensationslösung von 4.5-Dimethyl- 7-chlor-oxythionaphten, die man nach dem Schweizerpatent Nr. 156434 aus<B>100 kg 1.</B> 2- Dimethyl-4-chlorbenzol-5-thioglykolsäui-e und <B>300</B> Liter Chlorsulfonsäure erhält, wird etwa 12 Stunden gerührt, wobei man die Tem- peratur langsam auf 20<B>0</B> ansteigen lässt. Die tiefgrüne Lösung wird- dann auf Eiswasser gegossen. Dabei scheidet sich der 4.<B>6.</B> 4. 5'- Tetramethyl-7.7'-Dichlor-thioindigo als roter kristallinischer Niederschlag ab.
<I>Beispiel 2:</I> Wenn man das nach dem Schweizerpa tent Nr. 156434 gewonnene 4.5-Dimethyl-7- oblor-oxythionaphten in alkalischer Lösung mit Ferrieyankalium oder einem ähnlichen Oxydationsmittel behandelt, so erhält man den gleichen symmetrischen Thioindigo.
Method for the preparation of an indigoid vat dye. It was found that the 4,5-didiethyl-7-chloro-oxythionaphthene described in Swiss patent no. 156434 can be converted into indigoid ink dyes. The symmetrical thioindigo dye can be produced from it by treating with oxidizing agents,
which is a lively red-violet vat dye with excellent fastness to soda cooking. If the 4. 5-diniethyl-7-chloro-oxythionaphthene is condensed with eyclic diketones or their 2-derivatives (such as isatines and naphthisatines, their chlorides and arylides,
with Oxythionaphtenen and Naphtoxythionaphten and their anilene, also with Acenaph- tenchinon), respectively. if you place 4.
6-Dimethyl-7-chloro-oxythionapbten-2-anile with bodies containing a reactive methylene group, mixed thioindigo dyes are obtained, which dye the fiber from the vat in pink-red to blue tones, which fall-i In addition to their liveliness, they are characterized by an excellent fastness to soda cooking.
The present patent relates to a process for the preparation of an indigoid vat dye, characterized in that 4,5-dimethyl-7 - (, blor-oxythionaphthene is subjected to an oxidizing condensation.
The dyestuff obtained in this way has a bordeaux red color when dried, dissolves green in monohydrate, evaporates light yellow with caustic soda and hydrosulphite, dyes and prints on cotton in vivid red-violet tones with excellent cooking fastness and excels in this respect both in terms of clarity is the name of the nuance that is coloristically close to the <B> 5. </B> 5'-dichloro-7 <B>. </B> 7'-dimethyl-thioindigo. <I> Example <B> 1:
</B> </I> The condensation solution of 4.5-dimethyl-7-chloro-oxythionaphthene, which is obtained from <B> 100 kg of 1. </B> 2- dimethyl-4-chlorobenzene-5 according to Swiss patent no. 156434 -thioglykolsäui-e and <B> 300 </B> liters of chlorosulfonic acid is obtained, is stirred for about 12 hours, the temperature being allowed to rise slowly to 20 <B> 0 </B>. The deep green solution is then poured onto ice water. The 4th, 6th, 4th, 5'-tetramethyl-7.7'-dichloro-thioindigo separates out as a red crystalline precipitate.
<I> Example 2: </I> If the 4,5-dimethyl-7-oblor-oxythionaphthene obtained according to Swiss patent no. 156434 is treated in alkaline solution with potassium ferricyanide or a similar oxidizing agent, the same symmetrical thioindigo is obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE158249X | 1930-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH158249A true CH158249A (en) | 1932-11-15 |
Family
ID=5679368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH158249D CH158249A (en) | 1930-06-07 | 1931-05-18 | Process for the preparation of an indigoid vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH158249A (en) |
-
1931
- 1931-05-18 CH CH158249D patent/CH158249A/en unknown
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