AT35656B - Process for the preparation of halogen-containing vat dyes of the thioindigo series. - Google Patents
Process for the preparation of halogen-containing vat dyes of the thioindigo series.Info
- Publication number
- AT35656B AT35656B AT35656DA AT35656B AT 35656 B AT35656 B AT 35656B AT 35656D A AT35656D A AT 35656DA AT 35656 B AT35656 B AT 35656B
- Authority
- AT
- Austria
- Prior art keywords
- halogen
- preparation
- vat dyes
- thioindigo series
- containing vat
- Prior art date
Links
- 229910052736 halogen Inorganic materials 0.000 title description 4
- 150000002367 halogens Chemical class 0.000 title description 4
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000984 vat dye Substances 0.000 title description 3
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 title description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 239000007859 condensation product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
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EMI1.1
Durch das Patent Nr. 32206 ist ein Verfahren zur Darstellung halogensubstituierter Küpenfarbstoffe der Thioindigogruppe geschützt, welches darin besteht, dass man die durch Kondensation von Salicylthioessigsäure bezw. 3-Oxy-l-thionaphten mit Isatin bezw. dessen Homologen und Substitutionsproduktion erhältlichen Kondensationsprodukte bei Gegenwart eines indifferenten Lösungsmittels mit Halogen behandelt.
Es wurde nun gefunden, dass sich in ähnlicher Weise auch die gemäss engtischer Patentschrift Nr. 11760 vom Jahre 1906 durch Kondensation von Salicylthioessigsäure bezw. x-Oxythionaphten mit x-Isatinaryliden dargestellten rotvioletten bis blauen Küpenfarbstoffe durch Behandlung mit Halogenen in neue, wertvolle Farbstoffe überführen lassen, welche, verglichen mit den als Ausgangsmaterial dienenden Produkten, erheblich gesteigerte Affinität zur Baumwollfaser und bessere Waschechtheit aufweisen.
Die Darstellung der neuen Farbstoffe wird durch folgendes Beispiel erläutert : Beispiel : 4 Tl. des durch Kondensation von 1 Mol. α-Oxythionaphten mit 1 Mol.
α-Isatinanilid in Nitrobenzol gemäss englischer Patentschrift Nr. 11760 vom Jahre 19U6 dargestellten Kondensationsprodukts werden in 40 Tl. Nitrobenzol suspendiert, 6-8 Tl.
EMI1.2
Kristälichen, welche in konzentrierter Schwefelsäure mit blauer Farbe löslich sind. Beim Verdünnen der schwefelsauren Lösung mit Wasser fallen violettblaue Flocken aus. Rauchende Schwefelsäure löst den Farbstoff mit leuchtend blauer Farbe, welche auch beim Erwärmen ncht verändert wird. In heissem Alkohol ist er nur wenig löslich, ziemlich leicht in heissem Benzol, leicht in warmem Nitrobenzol mit blauvioletter Farbe. Beim Behandeln
EMI1.3
gute Waschechtheit aus.
In analoger Weise erfolgt die Darstellung der halogenderivate bei Verwendung der anderen gemäss Verfahren der englischen Patentschrift Nr. 11760 vom Jahre 1906 er-
EMI1.4
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EMI1.1
By the patent no. 32206 a process for the preparation of halogen-substituted vat dyes of the thioindigo group is protected, which consists in that one respectively by condensation of salicylthioacetic acid. 3-Oxy-l-thionaphten with isatin respectively. its homologues and substitution production available condensation products treated in the presence of an inert solvent with halogen.
It has now been found that, in a similar manner, according to the English patent no. 11760 from 1906, respectively, by condensation of salicylthioacetic acid. x-Oxythionaphten red-violet to blue vat dyes represented with x-isatinarylides can be converted into new, valuable dyes by treatment with halogens, which, compared to the products used as starting material, have a considerably increased affinity for cotton fibers and better wash fastness.
The preparation of the new dyes is illustrated by the following example: Example: 4 Tl. Of the by condensation of 1 mole of α-oxythionaphthene with 1 mole.
α-Isatin anilide in nitrobenzene according to English patent specification No. 11760 from 19U6 is suspended in 40 parts of nitrobenzene, 6-8 parts.
EMI1.2
Crystals which are soluble in concentrated sulfuric acid with a blue color. When the sulfuric acid solution is diluted with water, violet-blue flakes precipitate. Fuming sulfuric acid dissolves the dye with a bright blue color, which is not changed even when heated. It is only sparingly soluble in hot alcohol, fairly easily in hot benzene, slightly in warm nitrobenzene with a blue-violet color. When treating
EMI1.3
good wash fastness.
The representation of the halogen derivatives takes place in an analogous manner when using the other according to the method of the English patent specification No. 11760 from the year 1906.
EMI1.4
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT35656T | 1907-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT35656B true AT35656B (en) | 1908-12-28 |
Family
ID=3552273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT35656D AT35656B (en) | 1907-03-04 | 1907-03-04 | Process for the preparation of halogen-containing vat dyes of the thioindigo series. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT35656B (en) |
-
1907
- 1907-03-04 AT AT35656D patent/AT35656B/en active
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