DE97211C - - Google Patents
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- Publication number
- DE97211C DE97211C DENDAT97211D DE97211DA DE97211C DE 97211 C DE97211 C DE 97211C DE NDAT97211 D DENDAT97211 D DE NDAT97211D DE 97211D A DE97211D A DE 97211DA DE 97211 C DE97211 C DE 97211C
- Authority
- DE
- Germany
- Prior art keywords
- color
- dyes
- red
- oxygen
- alcohol
- 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- 230000001476 alcoholic Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 102100013068 CDCA4 Human genes 0.000 description 1
- 101700022879 CDCA4 Proteins 0.000 description 1
- 240000000218 Cannabis sativa Species 0.000 description 1
- MCPLVIGCWWTHFH-UHFFFAOYSA-L Methyl blue Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)[O-])=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[NH+]C=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S([O-])(=O)=O)=CC=2)C=C1 MCPLVIGCWWTHFH-UHFFFAOYSA-L 0.000 description 1
- JSFZIJCJVIGLSX-UHFFFAOYSA-N N(=O)CN(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N(=O)CN(C1=CC=CC=C1)C1=CC=CC=C1 JSFZIJCJVIGLSX-UHFFFAOYSA-N 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
- LGDPTPLJZGPOJL-UHFFFAOYSA-N N,N-dimethyl-2-nitrosoaniline Chemical compound CN(C)C1=CC=CC=C1N=O LGDPTPLJZGPOJL-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
- 206010039587 Scarlet fever Diseases 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- -1 p-tolyl- Chemical group 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
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002966 varnish Substances 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
- C09B17/00—Azine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
in BERLIN.in Berlin.
Verfahren zur Darstellung von Rosindonfarbstoffen.Process for the preparation of rosin dyes.
Patentirt im Deutschen Reiche vom 30. April 1897 ab.Patented in the German Empire on April 30, 1897.
©urch die Abhandlungen von O. Fischer und E. Hepp (Berl. Ber. 1896, 29, S. 2752) ist bekannt geworden, dafs Isorosindon durch Einwirkung von alkoholischem Kali, in ein© by the essays of O. Fischer and E. Hepp (Berl. Ber. 1896, 29, p. 2752) it has become known that isorosindone, by the action of alcoholic potash, is converted into a
Es wurde nun die Beobachtung gemacht, dafs die mittels tertiärer Amine erhältlichen Isorosinduline folgender Constitution sich wesentlich abweichend verhalten.The observation has now been made that those obtainable by means of tertiary amines Isorosindulins of the following constitution behave significantly differently.
In der Formel bedeutet R R1 bezw. R2 gleiche oder verschiedene aromatische oder fette Radicale.In the formula, RR means 1 respectively. R 2 are identical or different aromatic or fatty radicals.
Setzt man diese Verbindungen in Lösung oder feiner Suspension bei Gegenwart von Aetzalkali der Luft aus, oder fügt ein in alkalischer Lösung Sauerstoff abgebendes Mittel hinzu, so nehmen diese vorgenannten Körper leicht ein Atom Sauerstoff auf. Hierbei greift aber die Hydroxyl-Gruppe nicht, wie 1. c. angegeben, in den Benzolkern, sondern in den Orthosubstitutionsproduct, nämlich Oxyisorosindon übergeführt wird. Der Vorgang wird durch folgendes Formelbild veranschaulicht:If you put these compounds in solution or fine suspension in the presence of Caustic alkali from the air, or adds an oxygen-releasing agent in an alkaline solution in addition, these aforementioned bodies easily take up an atom of oxygen. This takes effect but not the hydroxyl group, as 1. c. indicated in the benzene nucleus, but in the Orthosubstitution product, namely Oxyisorosindon is transferred. The process will illustrated by the following equation:
Naphtalinkern ein. Es entstehen Rosindone von folgender typischer Form:Naphthalene core. Rosindones are produced in the following typical form:
Während die von O. Fischer und E; Hepp beschriebenen Verbindungen durch den Eintritt der Hydroxyl-Gruppe in ihrem Farbcharakter nicht geändert werden, unterscheiden sich diese neuen Farbstoffe wesentlich von ihren Ausgangskörpern. While that of O. Fischer and E; Hepp compounds described by the entry of the hydroxyl group in their color character are not changed, these new dyes differ significantly from their original substances.
Die letzteren färben tannirte Baumwolle blau bis blau violett, die neuen'Farbstoffe roth bis Scharlach. Die Isorosinduline lösen sich als einfache Benzolinduline roth bis violett in cone. Schwefelsäure, die neuen Producte mit derThe latter dye tannin cotton blue to blue-violet, the new dyes red to Scarlet fever. The isorosinduline dissolve as simple benzolinduline red to purple in cones. Sulfuric acid, the new products with the
typischen charakteristischen Rosindonfarbe: schmutzig-grün mit rothem Dichroismus.typical characteristic rosin color: dirty green with red dichroism.
Wie die Rosindone gehen die neuen Verbindungen bei der Reaction mit primären aromatischen Aminen und Diaminen in phenylirte Rosindulinderivate über, die sich mit der charakteristischen grasgrünen Farbe in cone. Schwefelsäure lösen. Es entstehen so Farbstoffe von blauer bis blauvioletter Nuance.Like the rosindones, the new compounds react with primary aromatic substances Amines and diamines are converted into phenylated rosindulin derivatives, which differ with the characteristic grass green color in cone. Dissolve sulfuric acid. This creates dyes from blue to blue-violet shade.
Das Isorosindulin aus p-Tolyl-ß-naphtylamin und Nitrosodiäthylanilin wird in 15 Theilen Alkohol gelöst und in der Kälte mit dem gleichen Gewicht cone. Natronlauge versetzt und offen stehen gelassen, bis die violette Farbe in eine rein-rothe von stark gelber Fluorescenz übergegangen ist. Bei Beendigung der Reaction ist ein grofser Theil des Rosindons in krystal-. !mischer Form ausgeschieden. Der Rest wird mit Wasser ausgefällt.The isorosindulin from p-tolyl-ß-naphthylamine and nitrosodiethylaniline is dissolved in 15 parts of alcohol and in the cold with the same weight cone. Sodium hydroxide solution added and left open until the purple color has passed into a pure red with a strong yellow fluorescence. At the end of the reaction a large part of the Rosindon is in crystal. ! mixed form excreted. The rest will precipitated with water.
Das Isorosindulin aus Nitrosodimethylanilin und Alkyl-ß-naphtylamin wird in 20 Theilen Wasser gelöst und mit 1 Theil cone. Natronlauge versetzt. Die Farbbase scheidet sich in violetten Flocken ab und verwandelt.sich beim Stehen an der Luft, schneller beim Schütteln mit Luft in gelbrothe Flocken des entsprechenden Rosindons. Die Reaction ist beendet, sobald eine abfi}trirte Probe-, sich in Alkohol mit scharlachrother Farbe und gelber Fluorescenz löst. Die neue Verbindung wird durch Filtration isolirt und läfst sich aus Alkohol oder anderen Lösungsmitteln in krystallisirfer Form erhalten.The isorosindulin from nitrosodimethylaniline and alkyl-β-naphthylamine is divided into 20 parts Dissolved water and with 1 part cone. Sodium hydroxide solution added. The color base separates into violet flakes and transforms. when standing in the air, faster when shaking with air in yellow-red flakes of the corresponding Rosindon. The reaction is over as soon as an abfi} trirte trial, get into alcohol with scarlet color and yellow fluorescence. The new compound is made by filtration isolates and dissolves in crystallized form from alcohol or other solvents obtain.
Selbstverständlich kann der Procefs auch in der Weise ausgeführt werden, dafs gewisse sauerstoffabgebende Mittel angewendet werden. Versetzt man bei Herstellung des in Beispiel I. beschriebenen Farbstoffes die alkalische, alkoholische Lösung mit 3 Theilen einer 4 proc. Wasserstoffsuperoxydlösung, so ist die beschriebene Reaction nach wenigen Minuten beendet. Of course, the process can also be carried out in such a way that certain oxygen-releasing agents are used. If one adds in the preparation of the example I. described dye the alkaline, alcoholic solution with 3 parts of a 4 per cent. Hydrogen peroxide solution, the reaction described is over after a few minutes.
Beispiel III.Example III.
3 Theile Isorosindulin aus Phenyl-ß-naphtylamin und Nit'rosomethyldiphenylamin werden in 150 Theilen Alkohol gelöst, mit 1 Theil Natronlauge versetzt. Beim Luftdurchleiten bildet sich das Rosindon, welches aus der Lösung mit Wasser gefällt wird.3 parts isorosindulin from phenyl-ß-naphthylamine and nitrosomethyldiphenylamine are dissolved in 150 parts of alcohol, with 1 part Sodium hydroxide solution added. When air is passed through, the Rosindon is formed, which from the Solution is precipitated with water.
Es löst sich in cone. Schwefelsäure grün, ist unlöslich in verdünnten Säuren, löslich in Alkohol und Eisessig mit rother Farbe.It dissolves in cone. Sulfuric acid green, is insoluble in dilute acids, soluble in Alcohol and glacial acetic acid with a red color.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE97211C true DE97211C (en) |
Family
ID=368277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT97211D Active DE97211C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE97211C (en) |
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0
- DE DENDAT97211D patent/DE97211C/de active Active
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