CH182402A - Process for the preparation of N, N'-dimethoxyaethyl-2,2'-dipyrazolanthrone. - Google Patents
Process for the preparation of N, N'-dimethoxyaethyl-2,2'-dipyrazolanthrone.Info
- Publication number
- CH182402A CH182402A CH182402DA CH182402A CH 182402 A CH182402 A CH 182402A CH 182402D A CH182402D A CH 182402DA CH 182402 A CH182402 A CH 182402A
- Authority
- CH
- Switzerland
- Prior art keywords
- dipyrazolanthrone
- preparation
- dimethoxyethyl
- agent
- dimethoxyaethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 aryl sulfonic acid ester Chemical class 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000012021 ethylating agents Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/04—Pyrazolanthrones
- C09B5/08—Dipyrazolanthrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
Verfahren zur Herstellung des NN'-Dimethogyaethyl-2,2'-dipyrazolanthrons. -Es wurde gefunden, dass ein N, N'-Di- methoxyäthyl-2, 2'-dipyrazolanthron herge stellt werden kann, wenn man auf 1 Mol 2,2'-Dipyrazolanthr#on 2 Mol eines ss-Methox- äthylierungsmittel zur Einwirkung bringt.
Das erhaltene N, N'-Dimetboxyätbyl-2, 2'-dipyrazolanthron stellt ein rotes Pulver dar, das sich in konzentrierter Schwefelsäure orange löst. Es färbt Baumwolle aus grün stichigblauer Küpe in sehr kräftigen roten Tönen von sehr guten Echtheitseigenschaften. Die Färbungen ändern beim Seifen nur sehr wenig, im Gegensatz zu denjenigen des N, N'-Diäthyl-2, 2'-dipyrazolantbrons, die beim Seifen sehr stark nach Blaurot springen.
Als P-Methoxäthylierungsmittel, die die Gruppe -CH2-CH2-0C113 abgeben, kom men beispielsweise der Glykolmonomethyl- äther der Formel HO-CH2-CH2-OCHS, die Halogenäthyl-rnethyläther der Formel Hal-CH2-CH2-OCHS sowie- insbesondere die Arylsulforrsäureester, wie zum Beispiel der p-Toluolsulfonsäureester des Glykolmono- methyläthers der Formel
EMI0001.0026
in Betracht.
Das Verfahren kann in Gegen wart oder Abwesenheit von Lösungs- oder Verdünnungsmitteln ausgeführt werden.
Beispiel: <I>,</I> 10,5 Teile trockenes, fein pulverisiertes Dikaliumsalz des 2, 2'-Dipyrazolantbrons werden in 70 Teilen Nitrobenzol suspendiert. Man gibt 14 Teile p-Toluolsulfonsäureester des Glykolmonomethyläthers zu und erhitzt unter Rühren. Bei etwa 140 tritt Reaktion ein und die Farbe des Gemisches wechselt von Braun nach Rot. Man rührt etwa 16 Stunden lang bei 150-160 und lässt dann erkalten. Der gebildete Farbstoff wird abge saugt und so lange abwechselnd mit Alkohol und Wasser ausgekocht, bis die Filtrate prak tisch farblos ablaufen. Hierauf wird getrocknet.
Process for the preparation of NN'-dimethogyaethyl-2,2'-dipyrazolanthrone. -It has been found that an N, N'-dimethoxyethyl-2, 2'-dipyrazolanthrone can be Herge if one mole of 2,2'-Dipyrazolanthron # on 2 mol of an s-methoxy ethylating agent to act brings.
The N, N'-dimetboxyätbyl-2, 2'-dipyrazolanthrone obtained is a red powder which dissolves orange in concentrated sulfuric acid. It dyes cotton from a green, pungent blue vat in very strong red tones with very good fastness properties. The colors change very little when soaking, in contrast to those of N, N'-diethyl-2,2'-dipyrazolantbron, which jump very strongly to blue-red when soaking.
As P-methoxyethylating agents which give off the group -CH2-CH2-0C113, for example, the glycol monomethyl ethers of the formula HO-CH2-CH2-OCHS, the haloethyl methyl ethers of the formula Hal-CH2-CH2-OCHS and, in particular, the Arylsulforrsäureester, such as, for example, the p-toluenesulphonic acid ester of the glycol monomethyl ether of the formula
EMI0001.0026
into consideration.
The process can be carried out in the presence or absence of solvents or diluents.
Example: <I>, </I> 10.5 parts of dry, finely powdered dipotassium salt of 2,2'-dipyrazolantbrone are suspended in 70 parts of nitrobenzene. 14 parts of p-toluenesulphonic acid ester of glycol monomethyl ether are added and the mixture is heated with stirring. At about 140, a reaction occurs and the color of the mixture changes from brown to red. The mixture is stirred for about 16 hours at 150-160 and then allowed to cool. The dye formed is sucked abge and boiled alternately with alcohol and water until the filtrates run off practically colorless. It is then dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH182402T | 1936-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH182402A true CH182402A (en) | 1936-02-15 |
Family
ID=4431544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH182402D CH182402A (en) | 1936-07-30 | 1935-03-08 | Process for the preparation of N, N'-dimethoxyaethyl-2,2'-dipyrazolanthrone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH182402A (en) |
-
1935
- 1935-03-08 CH CH182402D patent/CH182402A/en unknown
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