CH139703A - Process for the preparation of a nitrogenous vat dye. - Google Patents
Process for the preparation of a nitrogenous vat dye.Info
- Publication number
- CH139703A CH139703A CH139703DA CH139703A CH 139703 A CH139703 A CH 139703A CH 139703D A CH139703D A CH 139703DA CH 139703 A CH139703 A CH 139703A
- Authority
- CH
- Switzerland
- Prior art keywords
- works
- preparation
- nitrogenous
- acid
- dibenzanthrone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 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 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 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
- 239000000835 fiber Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 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 3
- 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
- 239000005749 Copper compound Substances 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines stickstoffhaltigen Itüpenfarbstoffes. Im Hauptpatent ist ein Verfahren zur Darstellung eines stickstoffhaltigen Küpen- farbstoffes beschrieben,
bei dem man 1 Mol. des durch Behandlung von Pyranthron mit Halogen in Chlorsulfonsäure erhältlichen Te- trahalogenpyranthrons mit 3 Mol. des durch Nitrieren von Dibenzanthron mit 'Salpeter säure in Nitrobenzol und Reduktion der entstandenen Nitroverbindung erhältlichen Aminodibenzanthrons und 1 Mod. 1-Amino- anthraebinon umsetzt.
Es wurde nun befunden, ,dass man einen neuen Küpenfarbstoff erhält, wenn man 1 Mol. Tetrahalogeninsodibenzanthron, er hältlich durch Halogenieren von Isadibenz- anthron in Chlorsulfonsäure, mit 2 Mol. Aminodibenzanthron,
erhältlich durch Reduk tion .des durch Nitrieren von Dibenzanthron in Nitrobenzol erhältlichen Nitrodibenzan- throns, und, 2 Mol. 1-Amino-anthrachinon um setzt. Die Kondensation führt man zweck mässig in hochsiedenden Verdünnungsmitt@_ln Lind unter Zusatz von säurebindenden Mit teln, wie Natrium.acetat, aus.
Vielfach ist es von Vorteil, Katalysatoren, beispielsweise Kupferverbindungen, zuzusetzen.
Der neue Farbstoff .löst sich in konzen trierter ;Schwefelsäure mit violetter Farbe Lind gibt mit alkalischer Hydrosulfitlösung eine blaue Küpenlösung, aus der die pflanz liche Faser in blaugrauen, hervorragend ech ten Tönen gefärbt wird. <I>Beispiel:</I> Eine Suspension von 7;
8 Teilen Tetra bromisodibenzanthron (dargestellt durch Bro- mieren von Isodbenzanthron in Chlorsulfon- säure), 10 Teilen Natriumacetat, 2 Teilen Kupferoxyd, 9,4 Teilen Aminodibenzanthron, 4,6 Teilen 1-Aminoanthraehinon in. 250 Tei len Nitrobenzol wird unter Rühren so lange gekocht, bis das Reaktionsprodukt praktisch bromfrei ist.
Dann arbeitet man in der üb- liGhen Weise .auf.
Process for the preparation of a nitrogen-containing itupe dye. The main patent describes a process for the preparation of a nitrogen-containing vat dye,
in which 1 mol. of the tetrahalogenopyranthrone obtainable by treating pyranthrone with halogen in chlorosulfonic acid with 3 mol. of the aminodibenzanthrone and 1 mod. 1-aminoanthraebinone obtainable by nitrating dibenzanthrone with nitric acid in nitrobenzene and reducing the nitro compound formed implements.
It has now been found that a new vat dye is obtained if 1 mol. Of tetrahalogeninsodibenzanthrone, obtainable by halogenating isadibenzanthrone in chlorosulfonic acid, with 2 mol. Of aminodibenzanthrone,
obtainable by reduction of the nitrodibenzanthrone obtainable by nitrating dibenzanthrone in nitrobenzene, and converts 2 mol of 1-amino-anthraquinone. The condensation is expediently carried out in high-boiling diluents and with the addition of acid-binding agents, such as sodium acetate.
It is often of advantage to add catalysts, for example copper compounds.
The new dye dissolves in concentrated sulfuric acid with a violet color and an alkaline hydrosulphite solution gives a blue vat solution from which the vegetable fibers are dyed in blue-gray, exceptionally real shades. <I> Example: </I> A suspension of 7;
8 parts of tetra-bromoisodibenzanthrone (prepared by brominating isodbenzanthrone in chlorosulfonic acid), 10 parts of sodium acetate, 2 parts of copper oxide, 9.4 parts of aminodibenzanthrone, 4.6 parts of 1-aminoanthraehinone in 250 parts of nitrobenzene are stirred for so long cooked until the reaction product is practically bromine-free.
Then you work up in the usual way.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE139703X | 1927-10-18 | ||
| CH138317T | 1928-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139703A true CH139703A (en) | 1930-04-30 |
Family
ID=25713154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139703D CH139703A (en) | 1927-10-18 | 1928-10-01 | Process for the preparation of a nitrogenous vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139703A (en) |
-
1928
- 1928-10-01 CH CH139703D patent/CH139703A/en unknown
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