CH139662A - Process for the preparation of a nitrogenous vat dye. - Google Patents
Process for the preparation of a nitrogenous vat dye.Info
- Publication number
- CH139662A CH139662A CH139662DA CH139662A CH 139662 A CH139662 A CH 139662A CH 139662D A CH139662D A CH 139662DA CH 139662 A CH139662 A CH 139662A
- Authority
- CH
- Switzerland
- Prior art keywords
- works
- preparation
- vat dye
- blue
- nitrogenous
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000984 vat dye Substances 0.000 title claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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 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 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 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
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 101150032584 oxy-4 gene Proteins 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
- 238000003756 stirring Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines stlekstoffhaltigen Küpenfarbstoffes. Im Haupt-patent ist ein Verfahren zur Darstellung eines stickstoffhaltigen Küpen- farbstoffes beschrieben, bei dem man<B>1</B> Hol.
des durch Behandlung von Pyranthron mir Halogen in Chlorsulfonsäure erhältlichen TetrahaJ,oo,enpyranthrons mit<B>3</B> Hol. des durch Nitrieren von Dibenza.nthron mit Sal petersäure in Nitrobenzol und Reduktion der entstandenen Nitroverbindun- erhältlichen Aminodibenzanthrons und<B>1</B> Hol. 1-Amino- anthrachinon umsetzt.
Es wurde nun gefunden, dass man einen neuen Küpenfarbsto-ff erhält, wenn man <B>1</B> Hol. 2.<B>3. 5.</B> 6-Tetraha.lo-genbenzol mit ') Hol. 1-Aminoant-lirachinon und 2 Hol. Aminodibenzanthron, erhältlich durch Reduk tion von in Nitrobenzol nitriertem Dibenz- anthron, umsetzt. Die Kondensation führt man zweckmässig in hochsiedenden Verdün- nungsmitteln und unter Zusatz von Säure bindenden Mitteln, wie Natriumacetat, aus.
Vielfacli ist es von Vorteil, Katalysatoren, beispielsweise Kupferverbindungen, zuzu setzen.
Der neue Farbstoff löst sich in konzen trierter Schwefelsäure mit violetter Farbe und gibt mit alkalischer Hydrosulfitlösung eine blaue, Küpenlösung, aus der die pflanz liche Faser in grünblauen, hervorragend ech ten Tönen gefärbt wird.<B>-</B> <I>Beispiel:</I> 20 Teile 2.<B>3-. 5.</B> 6-Tetrab-rombenzol, <B>23</B> Teile 1-Aminoanthrachinon und 47 Teile Aminodibenzanthron werden in<B>500</B> Teilen Nitrobenzol mit<B>76</B> Teilen Kupferoxy4 und <B>75</B> Teilen Natriumaeetat so lange unter Rüh ren gekocht, 'bis das Reaktionsprodukt prak tisch bromfrei ist.
Man saugt ab, wäscht mit heissem Nitrobenzol nach, kocht mit verdünn ter Salzsäure aus, wäscht neutral und trock net.
Process for the preparation of a vat dye containing nitrogen. The main patent describes a process for the preparation of a nitrogen-containing vat dye, in which one <B> 1 </B> Hol.
of the TetrahaJ, oo, enpyranthrons with <B> 3 </B> Hol, obtainable by treating pyranthrone with halogen in chlorosulphonic acid. of the aminodibenzanthrone and 1 hol. 1-Amino-anthraquinone converts.
It has now been found that you get a new vat dye when you get <B> 1 </B>. 2. <B> 3. 5. </B> 6-Tetraha.lo-genbenzol with ') Hol. 1-Aminoant-lirachinon and 2 Hol. Aminodibenzanthrone, obtainable by reducing dibenzanthrone nitrated in nitrobenzene, is converted. The condensation is expediently carried out in high-boiling diluents and with the addition of acid-binding agents, such as sodium acetate.
In many cases it is advantageous to add catalysts, for example copper compounds.
The new dye dissolves in concentrated sulfuric acid with a violet color and, with an alkaline hydrosulphite solution, creates a blue vat solution from which the vegetable fibers are dyed in green-blue, exceptionally real shades. <B> - </B> <I> Example : </I> 20 parts 2. <B> 3-. 5. 6-Tetrab-rombenzene, 23 parts 1-aminoanthraquinone and 47 parts aminodibenzanthrone are in <B> 500 </B> parts nitrobenzene with <B> 76 </B> parts Copper oxy4 and <B> 75 </B> parts of sodium acetate are boiled with stirring until the reaction product is practically bromine-free.
It is filtered off with suction, washed with hot nitrobenzene, boiled with dilute hydrochloric acid, washed neutral and dry.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE139662X | 1927-10-18 | ||
| CH138317T | 1928-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH139662A true CH139662A (en) | 1930-04-30 |
Family
ID=25713114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH139662D CH139662A (en) | 1927-10-18 | 1928-10-01 | Process for the preparation of a nitrogenous vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH139662A (en) |
-
1928
- 1928-10-01 CH CH139662D patent/CH139662A/en unknown
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