CH149901A - Process for the preparation of a vat dye. - Google Patents
Process for the preparation of a vat dye.Info
- Publication number
- CH149901A CH149901A CH149901DA CH149901A CH 149901 A CH149901 A CH 149901A CH 149901D A CH149901D A CH 149901DA CH 149901 A CH149901 A CH 149901A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- dye
- vat dye
- vat
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 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 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 150000004682 monohydrates Chemical class 0.000 description 3
- DAQLYWPFKCRXAZ-UHFFFAOYSA-N O=C(C1=CC=CC=C1C1)C2=C1C=CC(Br)=C2I Chemical compound O=C(C1=CC=CC=C1C1)C2=C1C=CC(Br)=C2I DAQLYWPFKCRXAZ-UHFFFAOYSA-N 0.000 description 2
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VCSZKSHWUBFOOE-UHFFFAOYSA-N dioxidanium;sulfate Chemical compound O.O.OS(O)(=O)=O VCSZKSHWUBFOOE-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Nüpenfarbstoffes. Im Ilauptpatent ist ein Verfahren zur Darstellung eines Küpenfarbstoffes-besehrie- ben, bei dem Antliantliron mit jodierenden Mitteln behandelt wird.
Es wurde nun gefunden, dass man einen Farbstoff von ähnlichen Eigenschaften er halten kann, wenn man Alonojodanthant#llron wie es erhalten werden kann, durch, Behand lung von Anthanthron mit Jod in wasser freier Schwefelsäure mit bromierenden Mit teln behandelt.
Man kann hierbei die bei der Herstellung des Jodanthanthrons gemäss den Verfahren des I-Iauptpa;tentes oder des sellweiz. Patentes Nr. 147164 erhaltene schwefelsaure Lösun7g des Jodanthanthrons verwenden, man spart so. die Iselierung des Ausgangskörpers.
Der erhaltene Farbstoff, ein Bromjod- anthanthron, bildet, aus Nitrobenzol umkri stallisiert, rote Nadeln und färbt aus rot violetter Küpe Baumwolle in echten schar lachroten Tönen.<B>-</B> <I>Beispiel<B>1:
</B></I> <B>10</B> Teile Jodanthantliron, dargestellt zum Beispiel gemäss den Angaben des Haupt patentes oder des schweizerischen Patentes Nr. 1471,64, werden unter Rühren langsam in 20 Teile flüs-siges Brom eingetragen. Ma.ii rührt bei Zimmertemperatur ungefähr<B>15</B> Stunden lang un.c1,erhält nach Entfernen des überschüssigen Broms nach den üblichen Methoden, zum Beispiel durch Abdampfen im Vakuum oder Auswaschen mit Natrium- bisulfit, Bromjodant-hanthron.
Das gleiche Produkt erhält man zum Bei spiel Mm Behandeln von feinverteiltem Jodanthanthron mit Broradampf oder beim Bromieren in Mon#ahydrat bei<B>60'<I>C.</I></B> <I>Beispiel 2:
</I> <B>30,6</B> Teile Anthanthron, dargestellt zum Beispiel durch Behandeln von<B>1 .</B> l'-Dinaph- tyl-8. 8-diearbons-äure mit konzentrierter Schwefelsäure, werden in<B>300</B> Teilen Mono- Uydrat auf 120'<B>C</B> erhitzt, worauf die Lö sung im Laufe einer Stunde mit<B>12,7</B> Tei len Jod versetzt und unter Rühren noch <B>1</B> Stunde lang auf 120 bis<B>130 ' C</B> erhitzt wird.
Darauf lässt man die Temperatur auf zirka<B>80 ' C</B> abkühlen, versetzt mit<B>10</B> Teilen Brom und rührt ungefähr<B>1</B> Stunde weiter bei<B>70</B> bis<B>80 ' C.</B> Die Aufarheituno, des so erhaltenen Bromjodanthanthrons geschieht entweder durell Ausgiessen der Monoliydrat-- lösung auf Eis oder zweckmässig durch lang sames Zutropfen von soviel Wasser zur er kalteten Monohydratlösung, bis sich das Oxoniumsulfat in Form von violetten Kri stallen abscheidet. Diese werden abgesaugt und mit Wasser zersetzt.
Process for the preparation of a pebble dye. In the main patent a process for the preparation of a vat dye is described, in which anti-liantlirone is treated with iodine agents.
It has now been found that you can keep a dye of similar properties if you alonojodanthant # llron as it can be obtained by treating anthanthrone with iodine in anhydrous sulfuric acid with brominating agents.
One can use the methods used in the production of iodantanthanthrone according to the process of the main patent or of selling wheat. Use the sulfuric acid solution of iodanthanthrone obtained in patent No. 147164, this saves money. the isolation of the original body.
The dye obtained, a bromoiodanthanthrone, when recrystallized from nitrobenzene, forms red needles and dyes cotton from a red-violet vat in real sharp, laugh-red tones. <B> - </B> <I> Example <B> 1:
</B> </I> <B> 10 </B> parts of iodantanthantlirone, represented for example according to the information of the main patent or the Swiss patent No. 1471,64, are slowly introduced into 20 parts of liquid bromine with stirring . Ma.ii stirs at room temperature for about 15 hours and, after removing the excess bromine by the usual methods, for example by evaporation in vacuo or washing with sodium bisulfite, bromoiodanthrone.
The same product is obtained, for example, by treating finely divided iodantanthanthrone with bromine vapor or when brominating in monohydrate at <B> 60 '<I> C. </I> </B> <I> Example 2:
</I> <B> 30.6 </B> parts of anthanthrone, made for example by treating <B> 1. </B> l'-dinaphthyl-8. 8-diacid with concentrated sulfuric acid, are heated in <B> 300 </B> parts of mono-hydrate to 120 ° C, whereupon the solution is heated to <B> 12, 7 </B> parts iodine are added and the mixture is heated for <B> 1 </B> hour to 120 to <B> 130 ° C </B> while stirring.
The temperature is then allowed to cool to about <B> 80 ° C </B>, <B> 10 </B> parts of bromine are added and stirring is continued for about <B> 1 </B> hour at <B> 70 < / B> to <B> 80 'C. </B> The Aufarheituno, the bromoiodanthrone obtained in this way is done either by pouring the monoliydrate solution onto ice or expediently by slowly adding enough water dropwise to the cold monohydrate solution until that Oxonium sulfate precipitates in the form of purple crystals. These are sucked off and decomposed with water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE149901X | 1928-05-29 | ||
| CH143400T | 1929-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH149901A true CH149901A (en) | 1931-09-30 |
Family
ID=25714277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149901D CH149901A (en) | 1928-05-29 | 1929-05-21 | Process for the preparation of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH149901A (en) |
-
1929
- 1929-05-21 CH CH149901D patent/CH149901A/en unknown
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