CH132217A - Process for the preparation of a vat dye of the anthracene series. - Google Patents
Process for the preparation of a vat dye of the anthracene series.Info
- Publication number
- CH132217A CH132217A CH132217DA CH132217A CH 132217 A CH132217 A CH 132217A CH 132217D A CH132217D A CH 132217DA CH 132217 A CH132217 A CH 132217A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- dye
- vat dye
- vat
- anthracene series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- 150000001454 anthracenes Chemical class 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000006418 Brown reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Küpenfarbstoffes der Anthracenreihe. Im Hauptpatent ist ein Verfahren zur Darstellung eines Küpenfarbstoffes, der als ms-Anthradianthr-on zu bezeichnen ist, be schrieben, bei dem allo-ms-Naphtodiacitron mit Aluminiumchlorid behandelt wird.
Es wurde nun gefunden, dass der gleiche Farbstoff auch entsteht, wenn man 2.2'-Di- methyl-ms-naphtodianthron der Einwirkung alkalischer Mittel unterwirft. Als alkalische Kondensationsmittel seien genannt: Natriurn- carbonat, Kaliumcarbonat, Bariumoxyd, Kali umbydroxyd oder alkoholische Kalilauge. Es ist vorteilhaft, in Anwesenheit von Lösungs mitteln zu arbeiten.
Bei dieser Kondensation findet wahrscheinlich eine Abspaltung von 4 Wasserstoffatomen statt, die zum Ringsystem des ms-Anthradianthrons führt -und in folgen dem Schema wiedergegeben ist
EMI0001.0015
Der erhaltene Farbstoff ist als ms-Anthra- dianthron zu bezeichnen und identisch mit dem im Hauptpatent beschriebenen. Er stellt ein hellbraunes Pulver dar, welches aus Nitro- benzol in braunen Nädelchen kristallisiert er halten werden kann, und löst sich in kon zentrierter Schwefelsäure mit violetter Farbe.
Baumwolle wird von ihm aus blauvioletter Küpe in ebensolchen Tönen angefärbt, die beim Waschen und Seifen in ein äusserst licht- und chlorechtes Goldgelb übergehen. <I>Beispiel 1:</I> 1 Teil 2.2'-Dimethyl-ms-naphtodianthron 110-120 in eine Schmelze von 5 Teilen Ätzkali und 5 Teilen Alkohol eingetragen. Man erwärmt auf 170-175 , hält weitere 6 Std. bei dieser Temperatur und nimmt die Schmelze mit Wasser auf. Nachdem der ge bildete Farbstoff durch Einblasen von Luft ausgefällt ist, saugt man ab. Das erhaltene braune Reaktionsprodukt kann durch Be handeln mit Hypochlorit gereinigt werden.
<I>Beispiel 2:</I> Man trägt 1 Teil 2.2'-Dimethyl-ms-naphto- dianthron bei 210 in eine Schmelze von 10 Teilen Ätzkali ein, hält weitere 2 Stunden bei 220-230 und arbeitet, wie in Beispiel angegeben, auf. Der erhaltene Farbstoff ist mit dem dort beschriebenen identisch. Beispiel 1 Teil 2.2'-Diinethyl-ms-naphtodianthron wird in 10 Teilen Nitrobenzol unter Rühren während 4 Stunden mit 4 Teilen Bariumoxyd gekocht. Man saugt ab und befreit den ge bildeten Farbstoff durch Aufkochen mit ver dünnter Salzsäure vom beigemengten Barium oxyd. Er ist mit dem nach Beispiel 1 er haltenen Produkt identisch.
Process for the preparation of a vat dye of the anthracene series. In the main patent, a process for the preparation of a vat dye, which is to be referred to as ms-anthradianthr-one, is written, in which allo-ms-naphtodiacitron is treated with aluminum chloride.
It has now been found that the same dye is also formed when 2.2'-dimethyl-ms-naphtodianthrone is subjected to the action of alkaline agents. Alkaline condensing agents that may be mentioned are: sodium carbonate, potassium carbonate, barium oxide, potassium hydroxide or alcoholic potassium hydroxide solution. It is advantageous to work in the presence of solvents.
During this condensation, 4 hydrogen atoms are likely to be split off, which leads to the ring system of the ms-anthradianthrone - and is shown in the following scheme
EMI0001.0015
The dye obtained is to be referred to as ms-anthradianthrone and is identical to that described in the main patent. It is a light brown powder which can be obtained from nitrobenzene crystallized in brown needles, and dissolves in concentrated sulfuric acid with a purple color.
He dyes cotton from a blue-violet vat in the same shades that turn into an extremely light- and chlorine-fast golden yellow when washed and soaped. <I> Example 1: </I> 1 part of 2.2'-dimethyl-ms-naphtodianthron 110-120 added to a melt of 5 parts of caustic potash and 5 parts of alcohol. The mixture is heated to 170-175, held at this temperature for a further 6 hours and the melt is absorbed in water. After the dye formed has precipitated by blowing in air, it is filtered off with suction. The brown reaction product obtained can be purified by treating with hypochlorite.
<I> Example 2: </I> 1 part of 2,2'-dimethyl-ms-naphthodianthrone is introduced at 210 into a melt of 10 parts of caustic potash, held at 220-230 for a further 2 hours and worked as indicated in the example , on. The dye obtained is identical to that described there. Example 1 Part of 2.2'-diinethyl-ms-naphtodianthrone is boiled in 10 parts of nitrobenzene with 4 parts of barium oxide for 4 hours while stirring. It is filtered off with suction and freed the dye formed by boiling it with dilute hydrochloric acid from the added barium oxide. It is identical to the product obtained in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128231T | 1927-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH132217A true CH132217A (en) | 1929-03-31 |
Family
ID=4386696
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH132216D CH132216A (en) | 1927-07-14 | 1927-07-14 | Process for the preparation of a vat dye. |
| CH132217D CH132217A (en) | 1927-07-14 | 1927-07-14 | Process for the preparation of a vat dye of the anthracene series. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH132216D CH132216A (en) | 1927-07-14 | 1927-07-14 | Process for the preparation of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH132216A (en) |
-
1927
- 1927-07-14 CH CH132216D patent/CH132216A/en unknown
- 1927-07-14 CH CH132217D patent/CH132217A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH132216A (en) | 1929-03-31 |
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