CH136268A - Process for the preparation of a valuable vat dye. - Google Patents
Process for the preparation of a valuable vat dye.Info
- Publication number
- CH136268A CH136268A CH136268DA CH136268A CH 136268 A CH136268 A CH 136268A CH 136268D A CH136268D A CH 136268DA CH 136268 A CH136268 A CH 136268A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation
- vat dye
- preparation
- carried out
- benzdianthrone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000000984 vat dye Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000011230 binding agent 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
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- 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 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 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 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
- 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
- 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
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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 Darstellung eines wertvollen Küpenfarbstof- fes beschrieben, bei .dem Aminodibenz- anthron, .das erhalten werden kann ,durch Reduktion des durch Nitrieren von Di- benzanthron entstehenden Mononitro:dibenz- a_nthrons, mit einem in 1-Stellung negativ substituierten Anthrachinon, kondensiert wird.
Es wurde nun gefunden, dass man einen ähnlichen wertvollen Küpenf arbstof f erhält, wenn man 4 Mol. Aminodibenzanthron, das erhalten werden kann durch Reduktion des durch Nitrieren von Dibenzanthron entste henden Mononitrodibenzanthrons, mit 1 Hol.
Tetrahalogen-ms-naphtodianthron, hergestellt aus Tetrahalogen-ms-benzdianthron, das durch direkte Halogenierung von ms-Benz- dia.nthron erhalten wird, durch Verbacken mit Aluminiumchlorid oder Oxydation mit Braunstein in Gegenwart von Schwefelsäure, kondensiert.
Die Kondensation führt mau zweckmässig in hochsiedenden Lösungs- oder Verdünnungsmitteln aus, und man kann hierbei auch säurebindende Mittel zusetzen. Vielfach ist die Anwendung von Katalysa toren vorteilhaft, als welche beispielsweise Gemische von Natriumacetat und Kupfer salzen benutzt werden können.
Der neue Küpenfarbstoff ist ein schwar zes Pulver; er ist in konzentrierter iSchwefel- säure mit violetter Farbe löslich und färbt Baumwolle aus blauer güpe in schwarzen, hervorragend echten Tönen.
<I>Beispiel:</I> Man suspendiert 47 Teile des Amino- dibenzanthrons in 1000 Teilen Nitrobenzol, gibt 15 Teile Natriumacetat, 3 Teile Kup feroxyd und 18 Teile Tetrabrom-ms-napbto- dianthron (dargestellt aus Tetrabrom-ms- benzdianthron durch Behandlung .mit Alu miniumchlorid) hinzu, worauf man unter Rühren bis zur Beendigung der Farbstoff- Bildung kocht. Darauf wird wie üblich .auf gearbeitet.
Man kann das Aminodibenzanthron während der Rektion, aus der entspre chenden Nitroverbindung und einem Re- ,duktionsmittel" zum Beispiel Hydrazin- hydrat oder Schwefel, erzeugen. Statt des Tetra'brom-ms-naphtodianthrons kann man zum Beispiel auch .das Tribrommonochlor- oder Tetraahlor-ms-naphtodianthron oder andere gemischte oder einheitlich vierfach halogensubstituierte ms-Naphtodianthrone verwenden.
Process for the preparation of a valuable vat dye. The main patent describes a process for the preparation of a valuable vat dye, in which aminodibenzanthrone, which can be obtained by reducing the mononitro produced by nitrating dibenzanthrone: dibenzanthron, with a negative in the 1-position substituted anthraquinone, is condensed.
It has now been found that a similar valuable vat dye is obtained if 4 moles of aminodibenzanthrone, which can be obtained by reducing the mononitrodibenzanthrone produced by nitration of dibenzanthrone, with 1 hol.
Tetrahalogen-ms-naphtodianthron, produced from tetrahalogen-ms-benzdianthron, which is obtained by direct halogenation of ms-Benz- dia.nthron, by baking with aluminum chloride or oxidation with manganese dioxide in the presence of sulfuric acid, condensed.
The condensation is expediently carried out in high-boiling solvents or diluents, and acid-binding agents can also be added. In many cases, the use of cata- tors 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 iSulphuric acid with a violet color and dyes cotton from blue güpe in black, outstandingly genuine shades.
<I> Example: </I> 47 parts of aminodibenzanthrone are suspended in 1000 parts of nitrobenzene, 15 parts of sodium acetate, 3 parts of copper oxide and 18 parts of tetrabromo-ms-napbtodianthrone (prepared from tetrabromo-ms-benzdianthrone by Treatment .mit aluminum chloride), whereupon the mixture is boiled with stirring until the dye has formed. As usual, it is worked on.
The aminodibenzanthrone can be produced during the reaction from the corresponding nitro compound and a reducing agent, for example hydrazine hydrate or sulfur. Instead of the tetra'brom-ms-naphtodianthrone, one can also use, for example, the tribromomonochloro or tetraahlor Use ms-naphtodianthrone or other mixed or uniformly fourfold halogen-substituted ms-naphtodianthrones.
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 |
|---|---|
| CH136268A true CH136268A (en) | 1929-10-31 |
Family
ID=25712133
Family Applications (32)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH137126D CH137126A (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. |
| CH136274D CH136274A (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. |
| CH136273D CH136273A (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. |
| CH137657D CH137657A (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. |
| CH136272D CH136272A (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. |
| CH136833D CH136833A (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. |
| CH136260D CH136260A (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. |
| CH137658D CH137658A (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. |
| CH137125D CH137125A (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. |
| CH137656D CH137656A (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. |
| CH136278D CH136278A (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. |
| CH136269D CH136269A (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. |
| CH136263D CH136263A (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. |
| CH136261D CH136261A (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. |
| CH136266D CH136266A (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. |
| CH136834D CH136834A (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. |
Family Applications Before (23)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH137126D CH137126A (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. |
| CH136274D CH136274A (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. |
| CH136273D CH136273A (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. |
| CH137657D CH137657A (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. |
| CH136272D CH136272A (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. |
| CH136833D CH136833A (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. |
| CH136260D CH136260A (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. |
| CH137658D CH137658A (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. |
| CH137125D CH137125A (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. |
| CH137656D CH137656A (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. |
| CH136278D CH136278A (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. |
| CH136269D CH136269A (en) | 1927-04-09 | 1928-04-04 | Process for the preparation of a valuable vat dye. |
Family Applications After (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH136263D CH136263A (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. |
| CH136261D CH136261A (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. |
| CH136266D CH136266A (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. |
| CH136834D CH136834A (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. |
Country Status (1)
| Country | Link |
|---|---|
| CH (32) | CH137126A (en) |
-
1928
- 1928-04-04 CH CH137126D patent/CH137126A/en unknown
- 1928-04-04 CH CH137124D patent/CH137124A/en unknown
- 1928-04-04 CH CH136274D patent/CH136274A/en unknown
- 1928-04-04 CH CH136267D patent/CH136267A/en unknown
- 1928-04-04 CH CH136273D patent/CH136273A/en unknown
- 1928-04-04 CH CH136277D patent/CH136277A/en unknown
- 1928-04-04 CH CH137657D patent/CH137657A/en unknown
- 1928-04-04 CH CH136279D patent/CH136279A/en unknown
- 1928-04-04 CH CH136272D patent/CH136272A/en unknown
- 1928-04-04 CH CH136265D patent/CH136265A/en unknown
- 1928-04-04 CH CH136833D patent/CH136833A/en unknown
- 1928-04-04 CH CH136275D patent/CH136275A/en unknown
- 1928-04-04 CH CH136260D patent/CH136260A/en unknown
- 1928-04-04 CH CH136262D patent/CH136262A/en unknown
- 1928-04-04 CH CH137658D patent/CH137658A/en unknown
- 1928-04-04 CH CH136270D patent/CH136270A/en unknown
- 1928-04-04 CH CH137125D patent/CH137125A/en unknown
- 1928-04-04 CH CH136264D patent/CH136264A/en unknown
- 1928-04-04 CH CH137656D patent/CH137656A/en unknown
- 1928-04-04 CH CH136832D patent/CH136832A/en unknown
- 1928-04-04 CH CH136278D patent/CH136278A/en unknown
- 1928-04-04 CH CH136276D patent/CH136276A/en unknown
- 1928-04-04 CH CH136269D patent/CH136269A/en unknown
- 1928-04-04 CH CH136268D patent/CH136268A/en unknown
- 1928-04-04 CH CH136263D patent/CH136263A/en unknown
- 1928-04-04 CH CH136830D patent/CH136830A/en unknown
- 1928-04-04 CH CH136261D patent/CH136261A/en unknown
- 1928-04-04 CH CH136831D patent/CH136831A/en unknown
- 1928-04-04 CH CH136266D patent/CH136266A/en unknown
- 1928-04-04 CH CH136271D patent/CH136271A/en unknown
- 1928-04-04 CH CH136834D patent/CH136834A/en unknown
- 1928-04-04 CH CH137127D patent/CH137127A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH136832A (en) | 1929-11-30 |
| CH136265A (en) | 1929-10-31 |
| CH137124A (en) | 1929-12-15 |
| CH136275A (en) | 1929-10-31 |
| CH136262A (en) | 1929-10-31 |
| CH136267A (en) | 1929-10-31 |
| CH137127A (en) | 1929-12-15 |
| CH136274A (en) | 1929-10-31 |
| CH136273A (en) | 1929-10-31 |
| CH136831A (en) | 1929-11-30 |
| CH137657A (en) | 1930-01-15 |
| CH136269A (en) | 1929-10-31 |
| CH137658A (en) | 1930-01-15 |
| CH136263A (en) | 1929-10-31 |
| CH136276A (en) | 1929-10-31 |
| CH136260A (en) | 1929-10-31 |
| CH136279A (en) | 1929-10-31 |
| CH136271A (en) | 1929-10-31 |
| CH136264A (en) | 1929-10-31 |
| CH137125A (en) | 1929-12-15 |
| CH136278A (en) | 1929-10-31 |
| CH136833A (en) | 1929-11-30 |
| CH136261A (en) | 1929-10-31 |
| CH136272A (en) | 1929-10-31 |
| CH136277A (en) | 1929-10-31 |
| CH136266A (en) | 1929-10-31 |
| CH137656A (en) | 1930-01-15 |
| CH136270A (en) | 1929-10-31 |
| CH136830A (en) | 1929-11-30 |
| CH137126A (en) | 1929-12-15 |
| CH136834A (en) | 1929-11-30 |
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