CH137125A - Process for the preparation of a valuable vat dye. - Google Patents
Process for the preparation of a valuable vat dye.Info
- Publication number
- CH137125A CH137125A CH137125DA CH137125A CH 137125 A CH137125 A CH 137125A CH 137125D A CH137125D A CH 137125DA CH 137125 A CH137125 A CH 137125A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation
- carried out
- preparation
- dibenzanthrone
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000000984 vat dye Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 claims description 6
- VZMULMSIWMLZLC-UHFFFAOYSA-N 2-aminoanthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=C(N)C=C3C3=CC=C4C1=C32 VZMULMSIWMLZLC-UHFFFAOYSA-N 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 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
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines wertvollen Küpenfarbstoffes. Im Hauptpatent ist ein Verfahren zur Dar stellung eines wertvollen Kiipenfarbstoffes be schrieben, bei dem Aminodibenzanthron, das erhalten werden kann durch Reduktion des durch Nitrieren von Dibenzanthron entstehen den Mononitrodibenzanthrons, mit einem in 1-Stellung negativ substituierten Anthrachinon kondensiert wird.
Es wurde nun gefunden, dass man einen ähnlichen wertvollen Küpenfarbstoff erhält, wenn man 2 Mol. Aminodibenzanthron, das er halten werden kann durch Reduktion des durch Nitrieren von Dibenzanthron entstehen den Mononitrodibenzanthrons, mit einem Mol. eines zweifach substituierten Dibenzanthrons, das durch Halogenieren von Dibenzanthron in Gegenwart eines organischen Lösungsmittels erhalten werden kann, kondensiert.
Durch die Halogenierung von Dibeuzanthron in organi schen Lösungsmitteln, zum Beispiel in Nitro- oder Trichlorbenzol, erhält man ein zweifach halogensubstituiertes Produkt, bei dem die Halogenatome sich stets an der gleichen Stelle des Moleküls befinden.
Die Kondensation führt man zweckmässig in hochsiedenden Lösungs- oder Verdünnungs mitteln aus, und man kann hierbei auch säure bindende Mittel zusetzen. Vielfach ist die Anwendung von Katalysatoren vorteilhaft, als welche beispielsweise Gemische von Natrium acetat und Kupfersalzen benutzt werden können.
Der neue Küpenfarbstoff ist ein schwarzes Pulver; er ist in konzentrierter Schwefelsäure mit violetter Farbe löslich und färbt Baum wolle aus blauer Küpe in blauschwarzen; her vorragend echten Tönen.
Beispiel Eine Suspension von 62 Teilen Dibrom- dibenzanthron in 1000- Teilen Nitrobenzol wird mit 94 Teilen Aminodibenzanthron, 50 Teilen Natriumacetat und 10 Teilen Kupferoxyd so lange unter Rühren gekocht, bis die Farb- stoffbildung beendet ist. Dann wird wie üblich aufgearbeitet. Man kann das Aminodibenzanthron wäh rend der Reaktion, aus der entsprechenden Nitroverbindung und einem Reduktionsmittel z. B. Hydrazinhydrat oder Schwefel erzeugen.
Statt des Dibromdibenzanthrons kann man auch die äquivalante Menge Dichlordibenz- anthron verwenden.
Process for the preparation of a valuable vat dye. The main patent describes a process for the preparation of a valuable Kiipen dye in which aminodibenzanthrone, which can be obtained by reducing the mononitrodibenzanthrone formed by nitrating dibenzanthrone, is condensed with an anthraquinone negatively substituted in the 1-position.
It has now been found that a similar valuable vat dye is obtained if 2 moles of aminodibenzanthrone, which it can be obtained by reducing the mononitrodibenzanthrone formed by nitrating dibenzanthrone, with one mole of a doubly substituted dibenzanthrone, which is obtained by halogenating dibenzanthrone can be obtained in the presence of an organic solvent, condensed.
Halogenation of dibeuzanthrone in organic solvents, for example in nitrobenzene or trichlorobenzene, gives a doubly halogen-substituted product in which the halogen atoms are always in the same position on the molecule.
The condensation is expediently carried out in high-boiling solvents or diluents, and acid-binding agents can also be added here. In many cases, the use of catalysts is advantageous, as which, for example, mixtures of sodium acetate and copper salts can be used.
The new vat dye is a black powder; it is soluble in concentrated sulfuric acid with a violet color and dyes cotton from a blue vat in blue-black; excellent real tones.
EXAMPLE A suspension of 62 parts of dibromodibenzanthrone in 1000 parts of nitrobenzene is boiled with 94 parts of aminodibenzanthrone, 50 parts of sodium acetate and 10 parts of copper oxide with stirring until the formation of color has ended. Then it is worked up as usual. You can the aminodibenzanthrone during the reaction, from the corresponding nitro compound and a reducing agent z. B. produce hydrazine hydrate or sulfur.
Instead of the dibromodibenzanthrone one can also use the equivalent amount of dichlorodibenzanthrone.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI30887A DE525109C (en) | 1927-04-09 | 1927-04-09 | Process for the representation of gray to black box dyes |
| CH133482T | 1928-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH137125A true CH137125A (en) | 1929-12-15 |
Family
ID=25712133
Family Applications (32)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH136834D CH136834A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136270D CH136270A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136279D CH136279A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137125D CH137125A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137124D CH137124A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137126D CH137126A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136833D CH136833A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136274D CH136274A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136272D CH136272A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136262D CH136262A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136265D CH136265A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136275D CH136275A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137656D CH137656A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136276D CH136276A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137127D CH137127A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136273D CH136273A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136278D CH136278A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137658D CH137658A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136271D CH136271A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136831D CH136831A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136264D CH136264A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137657D CH137657A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136267D CH136267A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136832D CH136832A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136269D CH136269A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136261D CH136261A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136830D CH136830A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136277D CH136277A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136268D CH136268A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136260D CH136260A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136263D CH136263A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136266D CH136266A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH136834D CH136834A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136270D CH136270A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136279D CH136279A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
Family Applications After (28)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH137124D CH137124A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137126D CH137126A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136833D CH136833A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136274D CH136274A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136272D CH136272A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136262D CH136262A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136265D CH136265A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136275D CH136275A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137656D CH137656A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136276D CH136276A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137127D CH137127A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136273D CH136273A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136278D CH136278A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137658D CH137658A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136271D CH136271A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136831D CH136831A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136264D CH136264A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH137657D CH137657A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136267D CH136267A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136832D CH136832A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136269D CH136269A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136261D CH136261A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136830D CH136830A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136277D CH136277A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136268D CH136268A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136260D CH136260A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136263D CH136263A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
| CH136266D CH136266A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (32) | CH136834A (en) |
-
1928
- 1928-04-04 CH CH136834D patent/CH136834A/en unknown
- 1928-04-04 CH CH136270D patent/CH136270A/en unknown
- 1928-04-04 CH CH136279D patent/CH136279A/en unknown
- 1928-04-04 CH CH137125D patent/CH137125A/en unknown
- 1928-04-04 CH CH137124D patent/CH137124A/en unknown
- 1928-04-04 CH CH137126D patent/CH137126A/en unknown
- 1928-04-04 CH CH136833D patent/CH136833A/en unknown
- 1928-04-04 CH CH136274D patent/CH136274A/en unknown
- 1928-04-04 CH CH136272D patent/CH136272A/en unknown
- 1928-04-04 CH CH136262D patent/CH136262A/en unknown
- 1928-04-04 CH CH136265D patent/CH136265A/en unknown
- 1928-04-04 CH CH136275D patent/CH136275A/en unknown
- 1928-04-04 CH CH137656D patent/CH137656A/en unknown
- 1928-04-04 CH CH136276D patent/CH136276A/en unknown
- 1928-04-04 CH CH137127D patent/CH137127A/en unknown
- 1928-04-04 CH CH136273D patent/CH136273A/en unknown
- 1928-04-04 CH CH136278D patent/CH136278A/en unknown
- 1928-04-04 CH CH137658D patent/CH137658A/en unknown
- 1928-04-04 CH CH136271D patent/CH136271A/en unknown
- 1928-04-04 CH CH136831D patent/CH136831A/en unknown
- 1928-04-04 CH CH136264D patent/CH136264A/en unknown
- 1928-04-04 CH CH137657D patent/CH137657A/en unknown
- 1928-04-04 CH CH136267D patent/CH136267A/en unknown
- 1928-04-04 CH CH136832D patent/CH136832A/en unknown
- 1928-04-04 CH CH136269D patent/CH136269A/en unknown
- 1928-04-04 CH CH136261D patent/CH136261A/en unknown
- 1928-04-04 CH CH136830D patent/CH136830A/en unknown
- 1928-04-04 CH CH136277D patent/CH136277A/en unknown
- 1928-04-04 CH CH136268D patent/CH136268A/en unknown
- 1928-04-04 CH CH136260D patent/CH136260A/en unknown
- 1928-04-04 CH CH136263D patent/CH136263A/en unknown
- 1928-04-04 CH CH136266D patent/CH136266A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH136279A (en) | 1929-10-31 |
| CH136273A (en) | 1929-10-31 |
| CH136834A (en) | 1929-11-30 |
| CH136274A (en) | 1929-10-31 |
| CH136267A (en) | 1929-10-31 |
| CH136830A (en) | 1929-11-30 |
| CH136264A (en) | 1929-10-31 |
| CH137126A (en) | 1929-12-15 |
| CH137657A (en) | 1930-01-15 |
| CH136261A (en) | 1929-10-31 |
| CH137127A (en) | 1929-12-15 |
| CH136269A (en) | 1929-10-31 |
| CH137658A (en) | 1930-01-15 |
| CH136266A (en) | 1929-10-31 |
| CH136270A (en) | 1929-10-31 |
| CH136268A (en) | 1929-10-31 |
| CH136832A (en) | 1929-11-30 |
| CH136272A (en) | 1929-10-31 |
| CH137656A (en) | 1930-01-15 |
| CH136275A (en) | 1929-10-31 |
| CH136276A (en) | 1929-10-31 |
| CH136271A (en) | 1929-10-31 |
| CH136278A (en) | 1929-10-31 |
| CH136262A (en) | 1929-10-31 |
| CH136833A (en) | 1929-11-30 |
| CH136263A (en) | 1929-10-31 |
| CH136265A (en) | 1929-10-31 |
| CH136277A (en) | 1929-10-31 |
| CH137124A (en) | 1929-12-15 |
| CH136260A (en) | 1929-10-31 |
| CH136831A (en) | 1929-11-30 |
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