CH199657A - Process for the preparation of N-monoisopropyl-N'-monomethyl-2,2'-dipyrazolanthrone. - Google Patents
Process for the preparation of N-monoisopropyl-N'-monomethyl-2,2'-dipyrazolanthrone.Info
- Publication number
- CH199657A CH199657A CH199657DA CH199657A CH 199657 A CH199657 A CH 199657A CH 199657D A CH199657D A CH 199657DA CH 199657 A CH199657 A CH 199657A
- Authority
- CH
- Switzerland
- Prior art keywords
- dipyrazolanthrone
- monomethyl
- monoisopropyl
- preparation
- blue
- Prior art date
Links
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 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
- 150000002148 esters Chemical class 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- SDQCGKJCBWXRMK-UHFFFAOYSA-N propan-2-yl 4-methylbenzenesulfonate Chemical compound CC(C)OS(=O)(=O)C1=CC=C(C)C=C1 SDQCGKJCBWXRMK-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 182402. Verfahren zur Herstellung des N-1VIonoisopropyl-N'-monomethyl-2,2'-dipyrazolanthrons. Fers wurde gefunden, d.ass .ein N-Monoiso- propyl-N'-monomethyl - 2;
2'-dipyrazolanthron hergestellt werden kann, wenn man auf 1 Mod 2,2'-Dipyrazolanthron 1 Mol eines Iso- propylierungsmittels und 1 Mol eines Methy- lierungsmittels zur Einwirkung bringt.
Das erhaltene N-Monoisopropyl-N'-mono- methyl-2,2'-.dipyrazo#lanthron stellt ein blau stichig rotes Pulver dar, ,das sich in konzen- trierter Schwefelsäure mit oranger Farbe löst. Es färbt Baumwolle aus grünstichig blauer güpe in hervorragend reinen, kräfti gen, roten Tönen von auegezeithneten Echt heitseigenschaften. Die Färbungen ändern beim -Seifen praktisch nicht.
Ale Isopropylierungsmittel- bezw. Methy- lierungsmittel können beispielsweise Isopro- pylalkohol bezw. Methylalkohol, sowie deren Ester, wie z. B. die Halogenwasserstoffsäure-, ,die Schwefelsäure- und besonders zweckmä ssig die Aryleulfonsäureeeter, verwendet wer den.
Das Verfahren kann in Gegenwart von Lösungs- oder Verdünnungsmitteln ausge führt werden.
<I>Beispiel:</I> 11 Teile trockenes, fein pulverisiertes Di- kaliumsalz,des 2,2'-Dipyrazolanthronyls und 2 Teile wasserfreie Pottasche werden in 100 Teilen Triehlorbenzol suspendiert. Man .gibt 4,7 Teile p-Toluolsulfonsäureisopropylester zu und rührt 6 Stunden bei 140'.
Nun wird auf<B>80'</B> abkühlen gelassen; dann fügt man nochmals 2 Teile wasserfreie Pottasche und anschliessend 7,5-Teile p-Toluolsulfonsäure- methylester zu. Man rührt weitere 4 :Stunden bei 140 und lässtdann abkühlen. Nach dem Absaugen wird der Rückstand mit Alkohol und Wasser gereinigt und getrocknet.
Additional patent to main patent No. 182402. Process for the preparation of N-1Vionoisopropyl-N'-monomethyl-2,2'-dipyrazolanthrone. It was also found that an N-monoisopropyl-N'-monomethyl - 2;
2'-dipyrazolanthrone can be prepared if 1 mol of an isopropylating agent and 1 mol of a methylating agent are brought into action on 1 mod of 2,2'-dipyrazolanthrone.
The N-monoisopropyl-N'-monomethyl-2,2 '-. Dipyrazo # lanthron is a blue-tinged red powder which dissolves in concentrated sulfuric acid with an orange color. It dyes cotton from a greenish blue güpe in exceptionally pure, strong, red tones with timeless fastness properties. The colors practically do not change when soaping.
Ale isopropylating agent respectively. Methylating agents can for example be or isopropyl alcohol. Methyl alcohol and their esters, such as. B. the hydrohalic acid, the sulfuric acid and particularly expedient ssig the Aryleulfonsäureeeter who used the.
The process can be carried out in the presence of solvents or diluents.
<I> Example: </I> 11 parts of dry, finely powdered dipotassium salt, of 2,2'-dipyrazole anthronyl and 2 parts of anhydrous potash are suspended in 100 parts of trilobenzene. 4.7 parts of isopropyl p-toluenesulfonate are added, and the mixture is stirred at 140 ° for 6 hours.
Let it cool down to <B> 80 '</B>; then another 2 parts of anhydrous potash and then 7.5 parts of methyl p-toluenesulfonate are added. The mixture is stirred for a further 4 hours at 140 and then allowed to cool. After suction, the residue is cleaned with alcohol and water and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH182402T | 1936-07-30 | ||
| CH199657T | 1936-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199657A true CH199657A (en) | 1938-08-31 |
Family
ID=25720721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199657D CH199657A (en) | 1936-07-30 | 1936-07-30 | Process for the preparation of N-monoisopropyl-N'-monomethyl-2,2'-dipyrazolanthrone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199657A (en) |
-
1936
- 1936-07-30 CH CH199657D patent/CH199657A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH199657A (en) | Process for the preparation of N-monoisopropyl-N'-monomethyl-2,2'-dipyrazolanthrone. | |
| CH199658A (en) | Process for the preparation of N-monoisopropyl-N'-monoethyl-2,2'-dipyrazolanthrone. | |
| CH199659A (en) | Process for the preparation of N-monoisopropyl-N'-monoethoxyethyl-2,2'-dipyrazolanthrone. | |
| DE706608C (en) | Process for the preparation of acidic anthraquinone dyes | |
| CH194958A (en) | Process for the preparation of N, N'-diisopropyl-2,2'-dipyrazolanthrone. | |
| CH209089A (en) | Process for the preparation of a water-soluble dye. | |
| CH199656A (en) | Process for the preparation of N, N'-di-sec-butyl-2,2'-dipyrazolanthrone. | |
| DE722868C (en) | Process for the production of Kuepen dyes of the anthraquinone series | |
| CH187927A (en) | Process for the preparation of N.N'-monomethoxyethyl-monoethoxyethyl-2.2'-dipyrazolanthrone. | |
| CH187928A (en) | Process for the preparation of N.N'-monoethyl-monomethoxyethyl-2.2'-dipyrazolanthrons. | |
| DE751345C (en) | Process for the production of acidic dyes of the anthraquinone series | |
| CH201961A (en) | Process for the preparation of a vat dye of the 4,5,9,10-dibenzopyrene-3,8-quinone series. | |
| CH232890A (en) | Process for the preparation of a new dye of the dioxazine series. | |
| CH186171A (en) | Process for the production of a vat dye. | |
| CH176243A (en) | Process for the separation of mixtures of isomeric vat dyes. | |
| CH196353A (en) | Process for the preparation of a pyrene derivative. | |
| CH175908A (en) | Process for the preparation of a nitrogen-containing condensation product. | |
| CH171232A (en) | Process for the production of a new azo dye. | |
| CH187926A (en) | Process for the preparation of the N.N'-diethoxyethyl-2.2'-dipyrazolanthrone. | |
| CH120172A (en) | Process for the production of a new dye. | |
| CH229128A (en) | Process for the preparation of a dye of the dioxazine series. | |
| CH174543A (en) | Process for the preparation of a whackfast dye of the anthraquinone series. | |
| CH174541A (en) | Process for the preparation of a whackfast dye of the anthraquinone series. | |
| CH217980A (en) | Process for the preparation of a new anthraquinone dye. | |
| CH182402A (en) | Process for the preparation of N, N'-dimethoxyaethyl-2,2'-dipyrazolanthrone. |