CH130618A - Process for the preparation of an orange-colored vat dye of the anthanthrone series. - Google Patents
Process for the preparation of an orange-colored vat dye of the anthanthrone series.Info
- Publication number
- CH130618A CH130618A CH130618DA CH130618A CH 130618 A CH130618 A CH 130618A CH 130618D A CH130618D A CH 130618DA CH 130618 A CH130618 A CH 130618A
- Authority
- CH
- Switzerland
- Prior art keywords
- orange
- bromine
- anthanthrone
- colored
- vat dye
- Prior art date
Links
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical class C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 9
- 239000000984 vat dye Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Verfahren zur Darstellung eines orange färbenden Küpenfarbstoffes der Anthanthronr eihe. Gegenstand des vorliegenden Patente:: ist ein Verfahren zur Darstellung eines rötlichen, orange färbenden Küpenfarbstoffes der Anthanthronreihe der wahrscheinlichen Formel:
EMI0001.0007
dadurch gekennzeichnet, dass man auf An- thanthron Brom in Gegenwart eines Ver dünnungsmittels einwirken lässt, so dass an nähernd 2 Atome Brom in das Molekül ein treten.
Trocken ist der so erhaltene Küpenfarb- stoff ein leuchtend rotes Pulver, löslich in konzentrierter Schwefelsäure mit leuchtend grüner Farbe. Er bildet mit alkalischem Hydrosulfit eine violette Küpe, aus der die vegetabilischen Fasern in gleichen Tönen an gefärbt werden, die durch Verhängen oder Seifen in ein leuchtendes Rotorange von her vorragender Echtheit, besonders Lichtecht heit, übergehen.
Beispiele 1. 1 Teil Anthanthron wird mit etwa 20 Teilen Nitrobenzol oder einem andern geeigneten organischen Lösungsmittel, wie zum Beispiel hochchloriertes Benzol, versetzt. Dann setzt man 3 Teile Brom zu und er wärmt unter Rühren auf 160 , bis keine Bromwasserstoffsäure mehr entweicht. Um die Reaktion zu Ende zu führen, wird kurz zum ]Kochen erhitzt.
Nach Abkühlen wird der abgeschiedene Farbstoff abfiltriert, mit dem angewandten Lösungsmittel und dann mit Sprit gewaschen und getrocknet. 2. 8 Teile Anthanthron werden in etwa 100 Teilen Schwefelsäure 66 B6 gelöst, dann 0,1 Teile Jod und 8 bis 6 Teile Brom zugefügt und das Ganze für einige Stun den auf etwa 50 bis<B>100'</B> erwärmt. Nach Beendigung der Reaktion giesst man auf Eis, filtriert und wäscht den ausgeschiede nen Farbstoff, wobei erforderlichenfalls etwa anhaftendes Brom in der üblichen Weise ent fernt wird.
Der so erhaltene Farbstoff ist praktisch identisch mit dem in Beispiel 1 beschriebenen Farbstoff.
Setzt man zu der schwefelsauren Lösun-,' des Anthanthrons so viel rauchende Schwe felsäure (zum Beispiel mit 65 % S03) zu, dass genügend S03 vorhanden ist, um die. durch die Reaktion gebildete Bromwasser stoffsäure wieder zu Brom zu oxydieren, so lässt sich die Bromierung des Anthanthrons mit der Hälfte der oben angegebenen Brom menge durchführen.
Dieses Verfahren kann vorteilhaft mit der Herstellung des Anthanthrons selbst ver bunden werden. Man verfährt dann etwa folgendermassen: 25 Teile 1.1'-Dinaphthyl- 8.8'-dicarbonsäure (vergleiche Patent Nr. 122066) werden allmählich in etwa. 200 Teile Schwefelsäuremonohydrat eingetragen, wo bei die Temperatur nicht über 60 steigen soll. Hierbei entsteht Anthanthron in quan titativer Ausbeute. Die Bromierung des ge bildeten Anthanthrons erfolgt dann wie oben beschrieben.
Process for the preparation of an orange-colored vat dye of the anthanthrone series. Subject of the present patent :: is a process for the preparation of a reddish, orange-colored vat dye of the anthanthrone series of the probable formula:
EMI0001.0007
characterized in that anthrone bromine is allowed to act in the presence of a diluent, so that approximately 2 atoms of bromine enter the molecule.
When dry, the vat dye obtained is a bright red powder, soluble in concentrated sulfuric acid with a bright green color. Together with alkaline hydrosulphite, it forms a violet vat from which the vegetable fibers are colored in the same tones, which are transformed into a bright red-orange with excellent authenticity, especially lightfastness, by hanging or soaking.
Examples 1. 1 part of anthanthrone is mixed with about 20 parts of nitrobenzene or another suitable organic solvent, such as, for example, highly chlorinated benzene. Then 3 parts of bromine are added and it is heated to 160 with stirring until no more hydrobromic acid escapes. To bring the reaction to the end, it is briefly heated to a boil.
After cooling, the deposited dye is filtered off, washed with the solvent used and then with fuel and dried. 2. 8 parts of anthanthrone are dissolved in about 100 parts of sulfuric acid 66 B6, then 0.1 part of iodine and 8 to 6 parts of bromine are added and the whole is heated to about 50 to <B> 100 '</B> for a few hours. After the reaction has ended, the mixture is poured onto ice, filtered and the precipitated dye is washed, with any bromine adhering to it being removed in the usual way.
The dye thus obtained is practically identical to the dye described in Example 1.
If one adds so much fuming sulfuric acid (for example with 65% SO3) to the sulfuric acid solution of the anthanthrone that enough SO3 is available to absorb the. To oxidize the hydrobromic acid formed by the reaction back to bromine, the bromination of the anthanthrone can be carried out with half the amount of bromine given above.
This method can advantageously be linked to the manufacture of the anthanthrone itself. The procedure is then approximately as follows: 25 parts of 1.1'-dinaphthyl-8.8'-dicarboxylic acid (see patent no. 122066) are gradually increased to about. 200 parts of sulfuric acid monohydrate entered, where the temperature should not rise above 60. This creates anthanthrone in quantitative yield. The bromination of the anthanthrone formed is then carried out as described above.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC37412D DE458598C (en) | 1925-11-07 | 1925-11-07 | Process for the production of orange dyes |
| CH124528T | 1926-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH130618A true CH130618A (en) | 1928-12-15 |
Family
ID=29216709
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH130617D CH130617A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
| CH135114D CH135114A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
| CH124528D CH124528A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
| CH131505D CH131505A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
| CH130618D CH130618A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
| CH147042D CH147042A (en) | 1925-11-07 | 1929-11-25 | Process for the production of an orange vat dye. |
| CH147699D CH147699A (en) | 1925-11-07 | 1929-12-02 | Process for the production of an orange vat dye. |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH130617D CH130617A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
| CH135114D CH135114A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
| CH124528D CH124528A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
| CH131505D CH131505A (en) | 1925-11-07 | 1926-11-02 | Process for the preparation of an orange-colored vat dye of the anthanthrone series. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH147042D CH147042A (en) | 1925-11-07 | 1929-11-25 | Process for the production of an orange vat dye. |
| CH147699D CH147699A (en) | 1925-11-07 | 1929-12-02 | Process for the production of an orange vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (7) | CH130617A (en) |
-
1926
- 1926-11-02 CH CH130617D patent/CH130617A/en unknown
- 1926-11-02 CH CH135114D patent/CH135114A/en unknown
- 1926-11-02 CH CH124528D patent/CH124528A/en unknown
- 1926-11-02 CH CH131505D patent/CH131505A/en unknown
- 1926-11-02 CH CH130618D patent/CH130618A/en unknown
-
1929
- 1929-11-25 CH CH147042D patent/CH147042A/en unknown
- 1929-12-02 CH CH147699D patent/CH147699A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH130617A (en) | 1928-12-15 |
| CH147699A (en) | 1931-06-15 |
| CH124528A (en) | 1928-03-16 |
| CH135114A (en) | 1929-08-31 |
| CH147042A (en) | 1931-05-15 |
| CH131505A (en) | 1929-02-15 |
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