DE97395C - - Google Patents
Info
- Publication number
- DE97395C DE97395C DENDAT97395D DE97395DA DE97395C DE 97395 C DE97395 C DE 97395C DE NDAT97395 D DENDAT97395 D DE NDAT97395D DE 97395D A DE97395D A DE 97395DA DE 97395 C DE97395 C DE 97395C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dyes
- blue
- alcohol
- soluble
- 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.)
- Active
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- 239000000975 dye Substances 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 4
- 150000001251 acridines Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000004961 triphenylmethanes Chemical class 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000001264 neutralization Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NIKFYOSELWJIOF-UHFFFAOYSA-O Fuchsine Chemical compound Cl.C1=C(N)C(C)=CC(C(=C2C=CC(=[NH2+])C=C2)C=2C=CC(N)=CC=2)=C1 NIKFYOSELWJIOF-UHFFFAOYSA-O 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 240000000358 Viola adunca Species 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- UCMYJOPIPDLTRT-UHFFFAOYSA-N N,N-diethyl-2-nitrosoaniline Chemical compound CCN(CC)C1=CC=CC=C1N=O UCMYJOPIPDLTRT-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N Safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
- XOSXWYQMOYSSKB-UHFFFAOYSA-L water blue Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=C(N)C(C)=CC(C(=C2C=CC(C=C2)=NC=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S(O)(=O)=O)=CC=2)=C1 XOSXWYQMOYSSKB-UHFFFAOYSA-L 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
- C09B56/00—Azo dyes containing other chromophoric systems
-
- 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
- C09B17/00—Azine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift Nr. 97118 ist ein Verfahren zur Darstellung von Safraninen beschrieben, welches darin besteht, dafs man auf Isorosinduline bei Gegenwart von Sauerstoff oder Sauerstoff abgebenden Mitteln Ammoniak oder primäre Amine bezw. Diamine einwirken läfst.In U.S. Patent No. 97118, there is one method for the preparation of saffranines, which consists in using isorosinduline in the presence of oxygen or oxygen-releasing agents ammonia or primary amines respectively. Act diamines running.
Bei weiterer Ausbildung dieses Verfahrens hat sich nun ergeben,-dafs man an Stelle der Amine auch freie Amidogruppen enthaltende Farbstoffe, wie z. B. Amidoazokörper, Farbstoffe-der Triphenylmethanreihe, Acridine, Induline etc., verwenden kann. Das Verfahren zur Herstellung von Safraninen bleibt in diesen Fällen im wesentlichen das gleiche; man verfährt am zweckmä'fsigsten so, dafs man moleculare Mengen des Isorosindulins und des Amidokörpers in Alkohol löst und die Oxydation bei Gegenwart überschüssiger Natronlauge durch ,den Luftsauerstoff oder durch Zugabe eines Oxydationsmittels bewirkt.With further development of this process it has now emerged that, instead of the Amines also contain dyes containing free amido groups, such as. B. amidoazo bodies, dyes-der Triphenylmethane series, acridines, indulins, etc., can use. The process of making saffronines remains in these Cases essentially the same; It is most expedient to proceed in such a way that molecular Quantities of isorosindulin and amido body in alcohol dissolve and oxidize in the presence of excess sodium hydroxide solution, the atmospheric oxygen or by adding of an oxidizing agent.
I. 2 Theile Neutralblau, 1,2 Theile salzsaures Amidoazobenzol werden in 30 Theilen Alkohol gelöst, mit einer cone, wässerigen Lösung von Ί Theil Potasche etwa 12 Stunden am Rückflufskühler gekocht. Der neue Farbstoff ist fast vollständig auskrystallisirt. Er ist in verdünnten mineralischen Säuren unlöslich, in cone. Schwefelsäure löslich mit gelbgrüner Farbe; in starker Essigsäure und in Alkohol löst er sich mit grüner Farbe.I. 2 parts of neutral blue and 1.2 parts of hydrochloric acid amidoazobenzene in 30 parts of alcohol dissolved, with a cone, aqueous solution of Ί Theil Potasche for about 12 hours on the reflux condenser cooked. The new dye is almost completely crystallized. He's in dilute mineral acids insoluble, in cone. Sulfuric acid soluble with yellow-green Colour; in strong acetic acid and in alcohol it dissolves with a green color.
II. 4 Theile Neutralblau, 3,5 Theile Fuchsin werden in 80 Theilen Alkohol gelöst, bei 25 bis 300 unter Rühren und Durchleiten von kohlensäurefreier Luft allmälig mit 2,5 Theilen Natronlauge von 40 ° B. versetzt. Das Condensationsproduct scheidet sich aus und läfst sich durch Lösen in mit Salzsäure angesäuertem Wasser und Fällen mit Kochsalz reinigen; es färbt tannirte Baumwolle blauviolett.II. 4 parts neutral blue, 3.5 parts Fuchsin are dissolved in 80 parts of alcohol, gradually added at 25 to 30 0 with stirring and passing carbon dioxide-free air with 2.5 parts of sodium hydroxide of 40 ° for example. The condensation product is separated out and can be purified by dissolving it in water acidified with hydrochloric acid and precipitating it with table salt; it dyes tannin cotton blue-violet.
III. Ersetzt man in Beispiel II das Fuchsin durch Phosphin und arbeitet im Uebrigen in analoger Weise, so erhält man einen wasserlöslichen grauschwarzen Farbstoff.III. If the fuchsine is replaced by phosphine in Example II and the rest of the work is carried out in in an analogous manner, a water-soluble gray-black dye is obtained.
IV. 4 Theile Neutralblau, 5 Theile des Safranin, welches nach dem Verfahren des Haupt - Patentes durch Einwirkung von p-Phenylendiamin auf das Isorosindulin aus Nitrosodiäthylanilin und Phenyl-ß-naphtylamin entsteht, und 2 Theile Potasche werden mit 100 Theilen Alkohol am Rückflufskühler gekocht. Die rothviolette Farbe der Lösung geht in eine blauviolette über. Die Bildung des Condensationsproductes wird bei Gegenwart von 2 Theilen Kupferoxyd beschleunigt. Der so entstehende Farbstoff ist bei Gegenwart freier mineralischer Säuren unlöslich und kann durch Ausziehen mit verdünnten Säuren daher von event, anhaftendem unveränderten Ausgangsmaterial befreit werden. Das neutraleIV. 4 parts of neutral blue, 5 parts of Safranin, which is obtained by the method of Haupt - Patentes due to the action of p-phenylenediamine on the isorosindulin Nitrosodiethylaniline and phenyl-β-naphthylamine are formed, and two parts of the potash are added 100 parts of alcohol boiled on the reflux condenser. The red-violet color of the solution turns into a blue-violet. The formation of the condensation product occurs in the presence accelerated by 2 parts of copper oxide. The resulting dye is in the presence Free mineral acids are insoluble and can therefore be extracted with diluted acids be freed from any adhering unchanged starting material. The neutral one
Salz löst sich in heifsem Wasser mit reinblauer Farbe und färbt tannirte Baumwolle blau.Salt dissolves in hot water with a pure blue color, and stains tannin cotton blue.
In analoger Weise verfährt man bei·' Anwendung anderer freie Amidogruppen enthaltender Farbstoffe; insofern dabei Producte entstehen, welche in Wasser zu schwer l'öslich sind, lassen sich aus denselben durch Einwirkung der - bekannten und gebräuchlichen Sulfurirungsmittel löslichere Sulfosäuren darstellen. One proceeds in an analogous way with '' application other dyes containing free amido groups; insofar as products arise which are too sparingly soluble in water can be obtained from them through action the - known and common sulfurizing agents represent more soluble sulfonic acids.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE97395C true DE97395C (en) |
Family
ID=368449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT97395D Active DE97395C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE97395C (en) |
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