DE126165C - - Google Patents
Info
- Publication number
- DE126165C DE126165C DENDAT126165D DE126165DA DE126165C DE 126165 C DE126165 C DE 126165C DE NDAT126165 D DENDAT126165 D DE NDAT126165D DE 126165D A DE126165D A DE 126165DA DE 126165 C DE126165 C DE 126165C
- Authority
- DE
- Germany
- Prior art keywords
- sulfur
- derivatives
- dyes
- melt
- dinitrobenzidine
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 4
- YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-N,N-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- BDZHBJPMMZFUJV-UHFFFAOYSA-N 4-[4-(diethylamino)phenyl]-N,N-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=CC=C(N(CC)CC)C=C1 BDZHBJPMMZFUJV-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N Potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000988 sulfur dye Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- -1 dinitro compound Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- C09B49/00—Sulfur dyes
- C09B49/02—Sulfur dyes from nitro compounds of the benzene, naphthalene or anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
M 126165 KLASSE 22 d. M 126165 CLASS 22 d.
Zusatz zum Patente 125699 vom 27. Mai 1900.Addendum to patent 125699 from May 27, 1900.
Patentirt im Deutschen Reiche vom 4. Dezember 1900 ab. Längste Dauer: 26. Mai 1915.Patented in the German Empire on December 4, 1900. Longest duration: May 26, 1915.
In der Patentschrift 125699 ist die Darstellung von Schwefelfarbstoffen aus o-Dinitrobenzidin und anderen Derivaten des 0-0'-Dinitrodiphenyls beschrieben. Es wurde nun gefunden, dafs auch in den Amidogruppen substituirte Benzidine, also z. B. das Tetramethylbenzidin und das Tetraäthylbenzidin sich in Nitroverbindungen überführen lassen, welche in hervorragender Weise zur Darstellung von Schwefelfarbstoffen geeignet sind.In the patent specification 125699 is the representation of sulfur dyes from o-dinitrobenzidine and other derivatives of 0-0'-dinitrodiphenyl. It has now been found that benzidines are also substituted in the amido groups, e.g. B. tetramethylbenzidine and the tetraethylbenzidine can be converted into nitro compounds, which are excellent for the preparation of Sulfur dyes are suitable.
Während das o-Dinitrobenzidin durch die Schwefelalkalischmelze in ein Schwarz übergeführt wird, ergeben die entsprechenden Nitroverbindungen der tertiären Benzidine braune Farbstoffe von grofser Reinheit der Nuance, grofser Färbekraft und vorzüglicher Echtheit.While the o-dinitrobenzidine is converted into a black by the sulfur-alkaline melt the corresponding nitro compounds of the tertiary benzidines give brown Dyes of great purity of shade, great tinting power and excellent fastness.
Wenn man z. B. eine Lösung von Tetramethylbenzidin in concentrirter Schwefelsäure in, der Weise, wie dies Täuber (Berichte 23, S. 795) für die Darstellung des o-Dinitrobenzidins beschrieben hat, durch allmähliches Eintragen einer 2 Molecülen entsprechenden Menge von Kalisalpeter nitrirt, so erhält man in theoretischer Ausbeute einen rothen Dinitrokörper, der, durch Umkrystallisiren gereinigt, bei 23 i° schmilzt.If you z. B. a solution of tetramethylbenzidine in concentrated sulfuric acid in, the way that Täuber (reports 23, p. 795) for the representation of the o-dinitrobenzidine by gradually adding an amount equal to 2 molecules nitrated by potassium nitrate, a red dinitro body is obtained in theoretical yield, which, purified by recrystallization, melts at 23 °.
ι Theil dieses Dinitrotetramethylbenzidins, 2 Theile Schwefel und 6 Theile Schwefelnatrium werden mit wenig Wasser angerührt und allmählich bis etwa 2300 erhitzt. Die Schmelze wird alsdann nach dem Erkalten gepulvert, das Pulver, wie in der Patentschrift 125699 angegeben, unter Vermeidung von Luftzutritt weiter erhitzt bis auf 280 bis 290° und so lange bei dieser Temperatur gehalten, bis die gewünschte Farbintensität und Nuance erreicht ist. Der so erhaltene Farbstoff stellt ein graphitartig glänzendes Pulver dar, welches sich in Wasser klar mit gelbrother Farbe löst. Durch Säure werden aus der Lösung gelblich braune Flocken gefällt. Der Farbstoff färbt ungeheizte Baumwolle in kaltem oder kochendem Bade mit einem sehr reinen gelbstichigen Braun.ι Dinitrotetramethylbenzidins part of this, 2 parts of sulfur and 6 parts of sodium sulphide are dissolved in a little water and gradually heated to about 230 0th The melt is then powdered after cooling, the powder, as indicated in patent specification 125699, heated to 280 to 290 ° while avoiding the ingress of air and kept at this temperature until the desired color intensity and nuance is achieved. The dye obtained in this way is a graphite-like, glossy powder which dissolves in water to give a clear solution with a yellowish-red color. Yellowish brown flakes are precipitated from the solution by acid. The dye dyes unheated cotton in a cold or boiling bath with a very pure yellowish brown.
Wird das Mengenverhältnifs der Bestandtheile der Schmelze geändert, so ändert sich die Nuance des Brauns. Letzteres fällt um so dunkler aus, je grofser die Menge des Schwefelnatriums ist im Verhältnifs zur angewendeten Schwefelmenge. Auch durch längeres und höheres Erhitzen wird die Nuance dunkler.If the proportions of the constituents of the melt are changed, it changes the shade of brown. The latter turns out all the darker, the greater the amount of sulphurous sodium is in proportion to the amount of sulfur used. The shade also becomes darker through longer and higher heating.
Aehnliche Farbstoffe erhält man, wenn man statt vom Tetramethylbenzidin vom Tetraäthylbenzidin ausgeht. Die Dinitroverbindung des Tetraäthylbenzidins bildet schöne, der Chromsäure ähnliche Nädelchen, welche bei 1140 schmelzen.Similar dyes are obtained when starting from tetraethylbenzidine instead of tetramethylbenzidine. The dinitro compound of Tetraäthylbenzidins forms fine, like chromic acid needles, melting at 114 0th
Claims (1)
Abänderung des Verfahrens des Patentes 125699, darin bestehend, dafs man an Stelle der dort verwendeten Derivate des o-Dinitrodiphenyls die durch Einwirkung von 2 Molecülen Salpeter bezw. der äquivalenten Menge Salpetersäure auf die schwefelsaure Lösung von Tetraalkylbenzidinen erhältlichen Dinitroderivate der Schwefel-Schwefelalkalischmelze unterwirft.Patent claim:
Modification of the process of patent 125699, in that instead of the derivatives of o-dinitrodiphenyl used there, the or. subjecting the equivalent amount of nitric acid to the sulfuric acid solution of tetraalkylbenzidines available dinitro derivatives of the sulfur-alkali metal melt.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE126165C true DE126165C (en) |
Family
ID=394839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT126165D Active DE126165C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE126165C (en) |
-
0
- DE DENDAT126165D patent/DE126165C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE126165C (en) | ||
| DE580012C (en) | Process for the preparation of dyes for cellulose esters or ethers | |
| DE658781C (en) | Process for the production of phthalocyanines | |
| DE555609C (en) | Process for the production of sulfur dyes | |
| AT61469B (en) | Process for the preparation of sulfur-containing dyes of the anthraquinone series. | |
| DE202639C (en) | ||
| DE138858C (en) | ||
| DE264292C (en) | ||
| DE131874C (en) | ||
| DE125587C (en) | ||
| DE232711C (en) | ||
| DE600250C (en) | Process for the production of chromium-containing azo dyes | |
| DE688908C (en) | Process for the production of sulfur-containing dyes | |
| DE139989C (en) | ||
| DE138839C (en) | ||
| DE255823C (en) | ||
| DE553001C (en) | Process for the preparation of acidic wool dyes | |
| DE167769C (en) | ||
| DE256515C (en) | ||
| DE114529C (en) | ||
| DE199979C (en) | ||
| AT75175B (en) | Process for the preparation of yellow sulfur dyes. | |
| DE137784C (en) | ||
| DE436943C (en) | Process for the preparation of dyes containing at least two nitro groups in the molecule | |
| DE197083C (en) |