CH187926A - Process for the preparation of the N.N'-diethoxyethyl-2.2'-dipyrazolanthrone. - Google Patents
Process for the preparation of the N.N'-diethoxyethyl-2.2'-dipyrazolanthrone.Info
- Publication number
- CH187926A CH187926A CH187926DA CH187926A CH 187926 A CH187926 A CH 187926A CH 187926D A CH187926D A CH 187926DA CH 187926 A CH187926 A CH 187926A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethoxyethyl
- dipyrazolanthron
- preparation
- agent
- dipyrazolanthrone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- -1 aryl sulfonic acid ester Chemical class 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application 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
- 238000004043 dyeing Methods 0.000 claims 1
- 239000012021 ethylating agents Substances 0.000 claims 1
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 239000003086 colorant 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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)
- Cosmetics (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 182402. Verfahren zur Herstellung des N. N'-Diäthoxyäthyl-2. 2'-dipyrazolanthrons. Es wurde gefunden, dass ein N. N' Diäthoxyäthyl-2.2'-dipyrazolanthron herge stellt werden kann, wenn man auf 1 Mol 2 . 2'-Dipyrazolanthron 2 Mol eines ss- Äthoxyäthylierungsmittels zur Einwirkung bringt.
Das erhaltene N . N'-Diäthoxyäthyl-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 Echtheitseigenschaf ten. Die Färbungen ändern beim Seifen nur sehr wenig.
<I>Beispiel:</I> 10,5 Teile trockenes, fein pulverisiertes Dikaliumsalz des 2.2'-Dipyrazolanthrons werden in 70 Teilen Nitrobenzol suspendiert. Man gibt 14,7 Teile p-Toluolsulfonsäure- ester des Glykolmonoäthyläthers zu und er hitzt 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 bis<B>160'</B> und lässt dann erkalten.
Der gebildete Farbstoff wird abgesaugt und so lange abwechselnd mit Alkohol und Wasser ausgekocht, bis die Filtrate praktisch farblos ablaufen. Hierauf wird getrocknet.
<B> Additional patent </B> to main patent no. 182402. Process for the production of N.N'-diethoxyethyl-2. 2'-dipyrazole anthrones. It has been found that a N. N 'diethoxyethyl-2.2'-dipyrazolanthrone can be Herge provides if one mole of 2 2'-Dipyrazolanthron brings 2 moles of a ss- ethoxyethylating agent to action.
The obtained N. N'-diethoxyethyl-2. 2'-dipyrazolanthron is a red powder that dissolves orange in concentrated sulfuric acid. It dyes cotton, greenish blue vat in very strong red tones with very good fastness properties. The colors change very little when soapy.
<I> Example: </I> 10.5 parts of dry, finely powdered dipotassium salt of 2.2'-dipyrazole anthrone are suspended in 70 parts of nitrobenzene. 14.7 parts of p-toluenesulfonic acid ester of glycol monoethyl ether are added and it 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 to 160' and then allowed to cool.
The dye formed is filtered off with suction and boiled alternately with alcohol and water until the filtrates run off practically colorless. It is then dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH187926T | 1935-03-08 | ||
| CH182402T | 1936-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH187926A true CH187926A (en) | 1936-11-30 |
Family
ID=25720716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH187926D CH187926A (en) | 1935-03-08 | 1935-03-08 | Process for the preparation of the N.N'-diethoxyethyl-2.2'-dipyrazolanthrone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH187926A (en) |
-
1935
- 1935-03-08 CH CH187926D patent/CH187926A/en unknown
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