DE68004C - Process for the preparation of a yellow basic dye of the auramine group from symmetrical diaethyldiamidodi - o - tolylmethane. (1 - Google Patents
Process for the preparation of a yellow basic dye of the auramine group from symmetrical diaethyldiamidodi - o - tolylmethane. (1Info
- Publication number
- DE68004C DE68004C DENDAT68004D DE68004DA DE68004C DE 68004 C DE68004 C DE 68004C DE NDAT68004 D DENDAT68004 D DE NDAT68004D DE 68004D A DE68004D A DE 68004DA DE 68004 C DE68004 C DE 68004C
- Authority
- DE
- Germany
- Prior art keywords
- symmetrical
- tolylmethane
- auramine
- preparation
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 3
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical group C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 title claims 2
- 239000000981 basic dye Substances 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001043 yellow dye Substances 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- -1 ethyl compound Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical group C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N N,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- MWOUGPLLVVEUMM-UHFFFAOYSA-N N-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 1
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 description 1
- KDFQYGBJUYYWDJ-UHFFFAOYSA-N azane;sodium Chemical compound N.[Na] KDFQYGBJUYYWDJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
PATENTAMPATENTAM
. Wird an Stelle des symmetrischen Dimethyldiamidodi-o-tolylmethans im Patent Nr. 67478 die entsprechende Aethylverbindung, nämlich symmetrisches Diäthyldiamidodi-o-tolylmethan, der gleichzeitigen Einwirkung von Schwefel und Ammoniak unterworfen, so entsteht ein neuer gelber Farbstoff, der in seinen Eigenschaften dem dort beschriebenen ähnlich ist, jedoch die Baumwolle noch grünstichiger färbt.. Used in place of the symmetrical dimethyldiamidodi-o-tolylmethane in patent no. 67478 the corresponding ethyl compound, namely symmetrical diethyldiamidodi-o-tolylmethane, when subjected to the simultaneous action of sulfur and ammonia, a new yellow dye, which is similar in its properties to the one described there, however, the cotton has an even greener tint.
Die Darstellung des Diäthyldiamidodi-otolylmethans kann nach dem im Patent Nr. 67478 für die Methylverbindung angegebenen Verfahren geschehen, indem man das Monomethyl-o-toluidin bei der Condensation mit Formaldehyd durch die äquivalente Menge Monoäthyl-o-toluidin ersetzt.The representation of diethyldiamidodi-otolylmethane can be according to that given in Patent No. 67478 for the methyl compound The process is done by using the monomethyl-o-toluidine in the condensation replaced with formaldehyde by the equivalent amount of monoethyl-o-toluidine.
Die neue Methanbase bildet schwach gelbliche Tafeln, die in heifsem Alkohol oder Ligroin leicht, in kaltem aber schwer löslich sind und bei 92 bis 93° schmelzen.The new methane base forms pale yellowish plates, which in hot alcohol or Ligroin are easily soluble in cold but sparingly soluble and melt at 92 to 93 °.
Beispiel: In einem geschlossenen, mit Rührwerk versehenen und im Oelbad befindlichen emaillirten Kessel werden 28,2 kg symmetrisches Diäthyldiamidoditolylmethan (Schmelzpunkt 92 bis 930 C.) mit 6,4 kg Schwefel geschmolzen und mit einem Verdünnungsmittel, beispielsweise einer Mischung von 240 kg Kochsalz und 14 kg Salmiak, vermischt. Man leitet hierauf während 7 bis 8 Stunden unter geringem Ueberdruck einen trockenen Strom von Ammoniakgas durch den Kessel, dessen OeIb ad temp era tür auf ca. 175 ° constant erhalten wird. Nach Verlauf dieser Zeit ist..die Reaction beendet.For example, in a closed, equipped with a stirrer and situated in an oil bath enamelled boiler be 28.2 kg symmetrical Diäthyldiamidoditolylmethan (melting point 92-93 0 C.) with 6.4 kg of sulfur and melted kg with a diluent, for example a mixture of 240 saline and 14 kg of ammonia, mixed. A dry stream of ammonia gas is then passed through the kettle for 7 to 8 hours under slight excess pressure, the oil of which is kept constant at about 175 ° ad temperature. After this time has elapsed, the reaction is ended.
Die erkaltete braune krystallinische Schmelze wird durch Ausziehen mit kaltem Wasser vom Kochsalz und Salmiak befreit, der Rückstand in Wasser von 80° C. gelöst und. aus der filtrirten Lösung der Farbstoff durch Zusatz von Kochsalz niedergeschlagen. Er krystallisirt aus Alkohol in Blättchen, ist leicht löslich in Wasser und Alkohol und färbt mit Tannin und Brechweinstein gebeizte Baumwolle reingelb mit grünem Stich. The cooled, brown crystalline melt is removed by pulling it out with cold water Freed sodium chloride and ammonia, the residue dissolved in water at 80 ° C. and. from the filtered solution of the dye precipitated by the addition of common salt. He crystallizes from alcohol in flakes, is easily soluble in water and alcohol and colors with tannin and tartar-stained cotton pure yellow with a green tinge.
Bei längerem Kochen der Farbstofflösung mit Mineralsäuren tritt Entfärbung unter Ammoniakabspaltung ein.If the dye solution is boiled with mineral acids for a long time, discoloration occurs with elimination of ammonia a.
Wird die wässerige Farbstofflösung mit Zinkstaub oder Natriumamalgam behandelt, so ■ tritt ebenfalls Entfärbung unter Bildung einer farblosen Leukoverbindung ein, welch letztere beim Erwärmen mit verdünnten Säuren in Ammoniak und das Diäthyldiamidotolylhydrol zerfällt.If the aqueous dye solution is treated with zinc dust or sodium amalgam, then ■ discoloration also occurs with the formation of a colorless leuco compound, the latter when heated with dilute acids in ammonia and the diethyldiamidotolylhydrol disintegrates.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE68004C true DE68004C (en) |
Family
ID=341579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT68004D Expired - Lifetime DE68004C (en) | Process for the preparation of a yellow basic dye of the auramine group from symmetrical diaethyldiamidodi - o - tolylmethane. (1 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE68004C (en) |
-
0
- DE DENDAT68004D patent/DE68004C/en not_active Expired - Lifetime
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