AT45479B - Process for the production of nitrogen-containing vat dyes of the thioindigo series. - Google Patents
Process for the production of nitrogen-containing vat dyes of the thioindigo series.Info
- Publication number
- AT45479B AT45479B AT45479DA AT45479B AT 45479 B AT45479 B AT 45479B AT 45479D A AT45479D A AT 45479DA AT 45479 B AT45479 B AT 45479B
- Authority
- AT
- Austria
- Prior art keywords
- nitrogen
- production
- vat dyes
- thioindigo series
- containing vat
- Prior art date
Links
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims 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 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 244000172533 Viola sororia Species 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von stickstoffhaltigen Küpenfarbstoffen der Thioindigoreihe.
Es wurde gefunden, dass die Polyhalogenthioindigos befähigt sind, beim Erhitzen mit Ammoniak oder primären Basen-zweckmässig unter Zusatz von Substanzen, welche den Austausch des Halogens, z. B. in der Anthrachinonreihe erleichtern, wie Kupfer, essigsaures Natron etc. - das Halogen, insbesondere Brom, teilweise auszutauschen, wobei neue stickstoffhaltige Küpenfarbstoffe entstehen.
Beispiel I : 20 Teile eines Pentabromthioindigos oder auch eines Tetrabromthioindigos,
EMI1.1
entstehen, werden mit etwa 150 Teilen 300/oigem Ammoniakwasser unter Zusatz von 1/2 Teil Kupferbronze mit oder ohne Zusatz von etwas Natriumazetat ungefähr 5 Stunden auf etwa 1200 erhitzt. Nach dem Absaugen und Auswaschen mit Wasser stellt das Produkt ein blauviolettes Pu1ver dar, welches Baumwolle und Wolle in violetten, sehr echten Tönen anfärbt. Das Produkt ist bromärmer geworden als das Ausgangsprodukt und zeigt gemäss der Stickstoffanalyse, dass Stickstoff eingetreten ist. Bei stärkerem Erhitzen werden noch blauere Produkte erhalten.
Beispiel 11 : 20 Teile Penta- oder Tetrabromthioindigo werden mit 60 Teilen p-Toluidin oder Anilin einige Stunden auf etwa If'QO oder kurze Zeit auf Siedetemperatur erhitzt, wobei man zweckmässig die für den leichteren Austausch von Halogen gegen Amin bekannt gewordenen Mittel, wie z. B. essigsaures Natron und Kupferpulver, zusetzen'kann.
Der nach Entfernung des überschüssigen Amins erhaltene Farbstoff stellt ein violettblaues Pulver dar, welches in der Hydrosulfitkiipe Baumwolle und Wolle in violetthlauen bis blauen Tönen anfärbt. Die Nuance ist um so blauer, je intensiver die Einwirkung des Amins war.
An Stelle des p-Toluidins, Anilins, o-Toluidins etc., können andere Monoamine, wie z. B. Monoäthylamin etc, verwandt worden. Ebenso können an Stelle des Polybromthio- indigos, wie z. B. die bromierten Dichlor-, Tetrachlorthioindigos, angewandt werden.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the production of nitrogen-containing vat dyes of the thioindigo series.
It has been found that the polyhalogen thioindigos are capable of, when heated with ammonia or primary bases, expediently with the addition of substances which replace the halogen, e.g. B. facilitate in the anthraquinone series, such as copper, acetic acid soda, etc. - to partially replace the halogen, especially bromine, with new nitrogen-containing vat dyes.
Example I: 20 parts of a pentabromothioindigo or a tetrabromothioindigo,
EMI1.1
arise, are heated with about 150 parts of 300% ammonia water with the addition of 1/2 part of copper bronze with or without the addition of a little sodium acetate for about 5 hours to about 1200. After vacuuming and washing with water, the product is a blue-violet powder which dyes cotton and wool in violet, very real tones. The product has become lower in bromine than the starting product and, according to the nitrogen analysis, shows that nitrogen has entered. With more intense heating, even bluer products are obtained.
Example 11: 20 parts of penta- or tetrabromothioindigo are heated with 60 parts of p-toluidine or aniline for a few hours to about If'QO or for a short time to the boiling point . B. acetic acid soda and copper powder, can add.
The dye obtained after removal of the excess amine is a violet-blue powder which, in the hydrosulfite section, dyes cotton and wool in violet-blue to blue shades. The more intense the action of the amine, the bluer the shade.
Instead of p-toluidine, aniline, o-toluidine, etc., other monoamines, such as. B. Monoethylamine etc, has been used. Likewise, instead of polybromothio indigo, such as. B. the brominated dichloro, tetrachlorothioindigos are used.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE45479X | 1908-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT45479B true AT45479B (en) | 1910-12-27 |
Family
ID=5625009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT45479D AT45479B (en) | 1908-11-13 | 1909-03-24 | Process for the production of nitrogen-containing vat dyes of the thioindigo series. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT45479B (en) |
-
1909
- 1909-03-24 AT AT45479D patent/AT45479B/en active
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