DE298099C - - Google Patents
Info
- Publication number
- DE298099C DE298099C DENDAT298099D DE298099DA DE298099C DE 298099 C DE298099 C DE 298099C DE NDAT298099 D DENDAT298099 D DE NDAT298099D DE 298099D A DE298099D A DE 298099DA DE 298099 C DE298099 C DE 298099C
- Authority
- DE
- Germany
- Prior art keywords
- brown
- dyes
- vat
- dye
- indoxyls
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000984 vat dye Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 9
- CRDNMYFJWFXOCH-BUHFOSPRSA-N Indirubin Natural products N\1C2=CC=CC=C2C(=O)C/1=C1/C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-BUHFOSPRSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- QCTZEHIRXZGGSD-UHFFFAOYSA-N 5,7-dibromo-1H-indole-2,3-dione Chemical compound BrC1=CC(Br)=CC2=C1NC(=O)C2=O QCTZEHIRXZGGSD-UHFFFAOYSA-N 0.000 description 1
- AYGGQJHJRFZDFH-UHFFFAOYSA-N 5,7-dichloro-1H-indole-2,3-dione Chemical compound ClC1=CC(Cl)=CC2=C1NC(=O)C2=O AYGGQJHJRFZDFH-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 229940097275 Indigo Drugs 0.000 description 1
- 240000007871 Indigofera tinctoria Species 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000002140 halogenating Effects 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile 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
- C09B7/00—Indigoid dyes
- C09B7/02—Bis-indole indigos
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Es wurde die bemerkenswerte Beobachtung gemacht, daß rotbraun bis gelbbraun färbende Küpenfarbstoffe durch Kondensation bestimmter, nämlich der in Stellung 6 durch eine Nitrogruppe oder einen Aminrest substituierten Indoxyle oder ihrer Acidylderivate mit Dihalogenisatinen entstehen. Beim Verküpen wird die Nitrogruppe des Farbstoffs zum Aminrest reduziert.The remarkable observation was made that red-brown to yellow-brown coloring Vat dyes by condensation of certain, namely that in position 6 by a nitro group or an amine radical-substituted indoxyls or their acidyl derivatives with dihalogenizatins develop. When vatting, the nitro group of the dye becomes the amine residue reduced.
ίο Daß die so erhältlichen Indirubine technisch wertvolle Farbstoffe sein würden, war nicht vorauszusehen, da die Indirubine bekanntlich meistens in der Küpe unbeständig sind und die Gefahr vorhanden war, daß im vorliegenden Falle die Zersetzlichkeit der Farbstoffe durch. die Nitro- bzw. Aminogruppe noch gesteigert werden könnte.ίο That the indirubins thus obtainable technically valuable dyes could not be foreseen, since the indirubins are well known are mostly inconsistent in the vat and there was a risk that in the present Fall through the decomposition of the dyes. the nitro or amino group is increased could be.
Die neuen Farbstoffe zeichnen sich neben ihrer .vollständigen Beständigkeit in der Küpe auch durch ihre Säure-, Chlor-, Licht- und Waschechtheit sowie durch ihre lebhafte gelbbraune Nuance aus. Der einzige bisher bekannt gewordene braune Küpenfarbstoff der Indigoreihe, der durch Halogenieren von 6-6-Diaminoindigo erhalten wurde, besitzt im Gegensatz zu den neuen Farbstoffen eine ungenügende ChIo r- und Säureechtheit.The new dyes stand out in addition to their complete stability in the vat also through their acid, chlorine, light and washfastness as well as their lively yellow-brown nuance. The only one known so far brown vat dye of the indigo series, obtained by halogenating 6-6-diaminoindigo was obtained, in contrast to the new dyes, has an insufficient ChIo r- and acid fastness.
220 Teile 5,7-Dichlorisatin und 262 Teile 6-Nitrodiacetylindoxyl werden in 2000 Teilen Eisessig heiß gelöst und nach Zusatz von 100 Teilen kpnzentrierter Salzsäure zwei Stunden auf dem Wasserbade erwärmt. Nach dem Erkalten wird der Farbstoff abgesaugt, gewaschen und getrocknet. Er bildet ein violettes, kupferglänzendes Krystallpulver, das sich in konzentrierter Schwefelsäure mit blauvioletter Farbe löst. In Benzol ist der Farbstoff in der Kälte unlöslich. Mit Hydrosulfit und Natronlauge gibt er eine gelbe Küpe mit brauner Blume, aus welcher die Textilfaser nach dem Oxydieren in echten braunen Tönen angefärbt wird. Die Echtheitseigenschaften werden noch verbessert, wenn man in das Farbstoffmolekül noch zwei Atome Brom einführt, ohne daß der Farbton wesentlich dadurch geändert wird.220 parts of 5,7-dichloroisatin and 262 parts of 6-nitrodiacetylindoxyl are used in 2000 parts Dissolved hot glacial acetic acid and after adding 100 parts of concentrated hydrochloric acid for two hours warmed up on the water bath. After cooling, the dye is filtered off with suction and washed and dried. It forms a purple, copper-shining crystal powder that is in concentrated sulfuric acid with a blue-violet color. In benzene, the dye is in the Cold insoluble. With hydrosulphite and caustic soda, he gives a yellow vat with a brown one Flower from which the textile fiber is dyed in real brown tones after oxidizing will. The fastness properties are improved when you look into the dye molecule introduces two more atoms of bromine without significantly changing the hue.
Desgleichen erhält man Farbstoffe ähnlicher Nuancen und Eigenschaften, wenn man an Stelle des 5,7-Dichlorisatins andere Dihalogenisatine, z. B. das 5,7-Dibromisatin, verwendet.Likewise, you get dyes of similar nuances and properties if you click on Place of 5,7-dichloroisatins other dihalosatins, z. B. the 5,7-dibromoisatin used.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE298099C true DE298099C (en) |
Family
ID=552332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT298099D Active DE298099C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE298099C (en) |
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0
- DE DENDAT298099D patent/DE298099C/de active Active
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