DE127438C - - Google Patents
Info
- Publication number
- DE127438C DE127438C DENDAT127438D DE127438DA DE127438C DE 127438 C DE127438 C DE 127438C DE NDAT127438 D DENDAT127438 D DE NDAT127438D DE 127438D A DE127438D A DE 127438DA DE 127438 C DE127438 C DE 127438C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- acid
- green
- water
- color
- 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
- 238000000034 method Methods 0.000 claims description 4
- IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical class OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- -1 4-Nitrooxyanthraquinonesulfonic acid Chemical compound 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HSIAJOAGTDCDCO-UHFFFAOYSA-N [N+](=O)([O-])OC1=C(C=2C(C3=CC=CC=C3C(C2C=C1)=O)=O)S(=O)(=O)O Chemical compound [N+](=O)([O-])OC1=C(C=2C(C3=CC=CC=C3C(C2C=C1)=O)=O)S(=O)(=O)O HSIAJOAGTDCDCO-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N Solvent Violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product 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
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/52—Amino-hydroxy-anthraquinones; Ethers and esters thereof sulfonated
- C09B1/523—N-substituted amino and hydroxy anthraquinone
- C09B1/525—N-aryl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
M 127438 KLASSE 22 b. M 127438 CLASS 22 b.
Zusatz zum Patente 101805 vom 3. September 1897.Addendum to patent 101805 of September 3, 1897.
Patentirt im Deutschen Reiche vom 5. November 189g ab. Längste Dauer: 13. Oktober 1909.Patented in the German Empire on November 5, 189g. Longest duration: October 13, 1909.
Es wurde gefunden, dafs, wenn man die ι · 4-Nitrooxyanthrachinonsulfosäure mit Aminen behandelt, man zu den Sulfosäuren des Alphylido-a-oxyanthrachinons (Chinizarinblau) gelangt. Die Reaction verläuft sehr glatt, ohne dafs die Sulfogruppe angegriffen wird.It has been found that if the ι · 4-Nitrooxyanthraquinonesulfonic acid with amines treated, one to the sulfonic acids of Alphylido-a-oxyanthraquinone (quinizarin blue) got. The reaction proceeds very smoothly without attacking the sulfo group.
Das Verfahren und auch der Reactionsverlauf (Ersatz von Nitrogruppen durch Aminreste) ist also analog demjenigen der Patentschrift 101805, hat aber den Vorzug, im Gegensatz zu diesem einheitlichere Producte zu liefern.The process and also the course of the reaction (replacement of nitro groups by amine residues) is therefore analogous to that of patent specification 101805, but has the advantage of im In contrast to this, to deliver more uniform products.
Eine für das Verfahren geeignete Nitrooxyanthrachinonsulfosäure kann z. B. erhalten werden durch successives Sulfiren und Nitriren von Erythrooxyanthrachinon. Man erhitzt z. B. 10 kg Erythrooxyanthrachinon mit 5 Th. Oleum von 20 pCt. auf 90 bis ioo° bis zur Wasserlöslichkeit. Nach dem Erkalten giefst man in 300 kg Wasser und salzt mit Sulfat aus. Man nitrirt nun das Natronsalz in bekannter Weise in cöncentrirter schwefelsaurer Lösung mit der berechneten Menge Nitrirsäure, giefst die Schmelze in Wasser und fällt mit Kochsalz aus. Die so erhaltene Nitrosulfosäure bildet feine gelbe Nädelchen, welche sich in cöncentrirter Schwefelsäure mit hellgelber Farbe lösen, die auf Zusatz von Borsäure in Gelbbraun übergeht; in verdünnter Natronlauge löst sich die Nitrosulfosäure mit rother Farbe. Sie besitzt folgende Constitution:A nitrooxyanthraquinone sulfonic acid suitable for the process can e.g. B. received are obtained by successive sulphuring and nitriding of erythrooxyanthraquinone. One heated z. B. 10 kg of erythrooxyanthraquinone with 5 parts of oleum of 20 pCt. to 90 to 100 ° up to water solubility. After cooling, it is poured into 300 kg of water and salted out with sulfate. The sodium salt is then nitrated in the known manner in concentrated sulfuric acid solution with the calculated amount of nitric acid, pour the Melt in water and precipitate with table salt. The nitrosulfonic acid thus obtained forms fine yellow needles, which dissolve in concentrated sulfuric acid with a light yellow color, which changes to yellow-brown on addition of boric acid; dissolves in dilute sodium hydroxide solution the nitrosulfonic acid with a red color. It has the following constitution:
OHOH
COCO
NO..NO ..
Die durch Einwirkung von Aminen erhaltenen Farbstoffe sind mithin nach folgendem Schema zusammengesetzt:The dyes obtained by the action of amines are therefore according to the following Composed scheme:
OHOH
COCO
NHRNHR
Das Verfahren zu ihrer Darstellung wird durch folgendes Beispiel erläutert:The procedure for their representation is explained by the following example:
Ein Gemenge von 10 kg Nitrooxyanthrachinonsulfosäure (Kalisalz), 200 kg 50 proc. Essigsäure und 100 kg p-Toluidin wird auf Wasserbadtemperatur längere Zeit (2 bis 3 Tage) erhitzt, bis die Schmelze eine dunkel grünblaue Färbung angenommen hat. Die Reac- A mixture of 10 kg of nitrooxyanthraquinone sulfonic acid (Potash salt), 200 kg 50 proc. Acetic acid and 100 kg of p-toluidine is added Water bath temperature heated for a long time (2 to 3 days) until the melt has taken on a dark green-blue color. The reac-
tionsmischung wird hierauf in verdünnte Salzsäure gegossen, der abgeschiedene Farbstoff abfiltrirt und nach bekannter Methode gereinigt. tion mixture is then poured into dilute hydrochloric acid, the deposited dye filtered off and purified by a known method.
Er ist in Wasser mit blauer Farbe schwer löslich, ebenfalls schwer löslich in verdünnter Natronlauge mit blaugrüner Farbe.It is sparingly soluble in water with a blue color, also sparingly soluble in diluted water Caustic soda with a blue-green color.
Die Lösung in concentrirter Schwefelsäure ist grün und wird auf Zusatz von Borsäure blau.The solution in concentrated sulfuric acid is green, and turns blue on the addition of boric acid.
Ungeheizte Wolle wird in röthlich blauen, chromgebeizte in grünblauen Nuancen angefärbt. Unheated wool is dyed in reddish blue, chrome-stained in green-blue shades.
In gleicher Weise werden, unter Zuhülfenahme anderer Amine, die analogen Farbstoffe dargestellt.In the same way, with the aid of other amines, the analogous dyes shown.
Die charakteristischen Eigenschaften einiger Vertreter dieser Gruppe sind in folgender Tabelle zusammengestellt:The characteristic properties of some representatives of this group are as follows Table compiled:
chinonsulfosäure -fNitrqerythrooxyanthra-
quinonsulfonic acid -f
Schwefelsäuremore concentrated
sulfuric acid
Schwefelsäure -+-
Borsäuremore concentrated
Sulfuric acid - + -
Boric acid
lich blauer Farbepoorly soluble with red
Lich blue color
blauer Farbepoorly soluble with
blue color
blauer Farbepoorly soluble with
blue color
Claims (1)
Weitere Ausbildung des Verfahrens des Patentes 101805 (Zusatz zu Patent 86150), darin bestehend, dafs man die daselbst verwendeten Nitrosulfosäuren hier, durch 1 · 4-Nitrooxyanthrachinonsulfosäure ersetzt.Patent Claim:.
Further development of the process of patent 101805 (addendum to patent 86150), which consists in replacing the nitrosulphonic acids used there with 1x4-nitrooxyanthraquinone sulphonic acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE127438C true DE127438C (en) |
Family
ID=396024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT127438D Active DE127438C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE127438C (en) |
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0
- DE DENDAT127438D patent/DE127438C/de active Active
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