DE230454C - - Google Patents
Info
- Publication number
- DE230454C DE230454C DENDAT230454D DE230454DA DE230454C DE 230454 C DE230454 C DE 230454C DE NDAT230454 D DENDAT230454 D DE NDAT230454D DE 230454D A DE230454D A DE 230454DA DE 230454 C DE230454 C DE 230454C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- yellow
- anthraquinone
- carboxylic acid
- acid
- 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
Links
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- -1 nitrogen containing anthraquinone derivatives Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 Acetic Acid Drugs 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- IOMZCWUHFGMSEJ-UHFFFAOYSA-N 4-(azaniumylamino)benzenesulfonate Chemical compound NNC1=CC=C(S(O)(=O)=O)C=C1 IOMZCWUHFGMSEJ-UHFFFAOYSA-N 0.000 description 1
- LLSVGXGSYBLMNY-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)Cl LLSVGXGSYBLMNY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C09B5/16—Benz-diazabenzanthrones, e.g. anthrapyrimidones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paints Or Removers (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde die Beobachtung gemacht, daß Anthrachinon-a-carbonsäure sowie ihre Derivate sehr leicht mit Hydrazinen reagieren.It was observed that anthraquinone-α-carboxylic acid and its derivatives react very easily with hydrazines.
Unter Verwendung von Phenylhydrazin z. B. verläuft die Reaktion nach folgender Gleichung :Using phenylhydrazine e.g. B. the reaction proceeds according to the following equation :
N-C6H5 NC 6 H 5
CO2HCO 2 H
NH,-NH.C6H, = NH, -NH.C 6 H, =
4040
4545
2H2O.2H 2 O.
An Stelle von Phenylhydrazin können andere Hydrazine benutzt werden.Other hydrazines can be used in place of phenylhydrazine.
5 Teile Anthrachinoncarbonsäurechlorid werden in 30 Teilen Pyridin gelöst, 2,4 Teile einer5 parts of anthraquinone carboxylic acid chloride are dissolved in 30 parts of pyridine, 2.4 parts of one
ao 50 prozentigen Hydrazinhydratlösung hinzugefügt und unter Schütteln einige Zeit erwärmt. Durch Hinzugabe von verdünnter Natronlauge (2,5 Teile Ätznatron enthaltend) erhält man eine klare gelbe Lösung, aus der das neue Kondensationsprodukt durch verdünnte Essigsäure in fast farblosen Blättchen abgeschieden wird. Es ist unlöslich in Wasser, Alkohol, Äther und wird in der Siedehitze von Anilin und Pyridin mit gelblicher Farbe gelöst.ao 50 percent hydrazine hydrate solution added and warmed for some time while shaking. The addition of dilute sodium hydroxide solution (containing 2.5 parts of caustic soda) is obtained a clear yellow solution from which the new condensation product by dilute acetic acid is deposited in almost colorless leaflets. It is insoluble in water, alcohol, Ether and is dissolved in the boiling heat of aniline and pyridine with a yellowish color.
Konzentrierte Schwefelsäure löst mit gelber Farbe und grüner Fluoreszenz und verdünnte Natronlauge mit gelber Farbe.Concentrated sulfuric acid dissolves with yellow color and green fluorescence and dilutes Caustic soda with yellow color.
25 Teile Anthrachinon-a-carbonsäure, 250 Teile Eisessig, 32 Teile Phenylhydrazin werden rückfließend zum Sieden erwärmt. Die Säure löst sich hierbei erst auf und nach einiger Zeit scheidet sich das Kondensationsprodukt in gelben Nadeln aus; es wird filtriert, mit Alkohol gewaschen und dann mit Soda ausgekocht. Es bildet gelbe, in Wasser, Lauge, Alkohol und Äther unlösliche Nadeln, die bei 286° unkorrigiert schmelzen. Sie lösen sich gut in der Hitze in Pyridin und Anilin mit gelber Farbe. Konzentrierte Schwefelsäure wird orange gefärbt und fluoresziert schwach grün.25 parts of anthraquinone-a-carboxylic acid, 250 parts of glacial acetic acid, 32 parts of phenylhydrazine are used refluxed to the boil. The acid only dissolves here and after a while After a while, the condensation product separates out in yellow needles; it is filtered, with Alcohol washed and then boiled with soda. It forms yellow, in water, lye, Alcohol and ether insoluble needles that melt uncorrected at 286 °. They are breaking up good in the heat in pyridine and aniline with yellow color. Concentrated sulfuric acid turns orange and fluoresces weakly green.
10 Teile Anthrachinon-a-carbonsäure, 8 Teile Phenylhydrazin-p-sulfosäure, 17 Teile Natriumacetat und 150 Teile Wasser werden rückfließend zum Sieden erhitzt, wobei nach kurzer Zeit völlige Lösung eingetreten ist. Die Flüssigkeit färbt sich beim Kochen allmählich dunkelgelb und erstarrt plötzlich zu einem Kristall- brei. Das ausgeschiedene gelbe Natriumsalz wird abfiltriert und mit etwas Wasser ge-10 parts of anthraquinone-a-carboxylic acid, 8 parts of phenylhydrazine-p-sulfonic acid, 17 parts of sodium acetate and 150 parts of water are refluxed to the boil, after a short time Time complete solution has occurred. The liquid gradually turns dark yellow when boiled and suddenly solidifies into a crystal porridge. The precipitated yellow sodium salt is filtered off and mixed with a little water
Wäschen; eine kleine Menge läßt sich noch aus der Lauge durch Kochsalz abscheiden. Das Salz bildet gelbe Blättchen, die gut in Wasser mit gelber Farbe löslich sind, während sie von organischen Lösungsmitteln nicht aufgenommen werden. Die Lösung in konzentrierter Schwefelsäure ist orange und erscheint im auffallenden Licht schön rot.Washes; a small amount can still be used Separate from the lye with table salt. The salt forms yellow leaflets that fit well in Water with yellow color are soluble, while they are not absorbed by organic solvents will. The solution in concentrated sulfuric acid is orange and appears nice red in the light.
Die nach dem Verfahren der vorliegenden ίο Erfindung erhältlichen Produkte sollen als Farbstoffe bzw. als Rohmaterialien zur Herstellung von· Farbstoffen Verwendung finden.The products obtainable by the process of the present invention are intended as Find dyes or as raw materials for the production of dyes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE230454C true DE230454C (en) |
Family
ID=490663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT230454D Active DE230454C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE230454C (en) |
-
0
- DE DENDAT230454D patent/DE230454C/de active Active
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