DE1050472B - Process for the preparation of highly soluble dyes of the auramm series in alcohols - Google Patents
Process for the preparation of highly soluble dyes of the auramm series in alcoholsInfo
- Publication number
- DE1050472B DE1050472B DENDAT1050472D DE1050472DA DE1050472B DE 1050472 B DE1050472 B DE 1050472B DE NDAT1050472 D DENDAT1050472 D DE NDAT1050472D DE 1050472D A DE1050472D A DE 1050472DA DE 1050472 B DE1050472 B DE 1050472B
- Authority
- DE
- Germany
- Prior art keywords
- alcohols
- auramine
- series
- water
- parts
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 21
- 150000001298 alcohols Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical class C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 150000002823 nitrates Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical class ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 150000002826 nitrites Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KSCQDDRPFHTIRL-UHFFFAOYSA-N auramine O Chemical compound [H+].[Cl-].C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 KSCQDDRPFHTIRL-UHFFFAOYSA-N 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal nitrites Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical class [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- DTJAPYHTDACJJX-UHFFFAOYSA-N bis[3-methyl-4-(methylamino)phenyl]methylideneazanium;chloride Chemical compound Cl.C1=C(C)C(NC)=CC=C1C(=N)C1=CC=C(NC)C(C)=C1 DTJAPYHTDACJJX-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Die Farbstoffe der Auraminreihe kommen allgemein als Hydrochloride in den Handel. Sie sind in dieser Form leicht wasserlöslich, aber in Alkoholen und Lacken nur mäßig löslich. Sie eignen sich daher z. B. nicht für die Herstellung von Gummidruckfarben. The dyes of the auramine series are generally marketed as hydrochlorides. You are in this Form slightly soluble in water, but only moderately soluble in alcohols and paints. They are therefore suitable z. B. not for the production of rubber printing inks.
Es wurde nun gefunden, daß man in Alkoholen gut lösliche Farbstoffe der Auraminreihe, die sich hervorragend zum Färben von Lacken und für die Herstellung von Gummidruckfarben eignen, in einfacher Weise erhält, wenn man wasserlösliche Salze von Auraminfarbstoffen mit wasserlöslichen Salzen der Salpetersäure oder der salpetrigen Säure, insbesondere mit Alkalinitriten und -nitraten, umsetzt. Es bilden sich dabei die bisher unbekannten, gut kristallisierenden Nitrite bzw. Nitrate der Auraminfarbstoffe.It has now been found that dyes of the auramine series which are readily soluble in alcohols and which are excellent suitable for coloring lacquers and for the production of rubber printing inks, in a simple way Way, if you get water-soluble salts of auramine dyes with water-soluble salts of the Nitric acid or nitrous acid, especially with alkali metal nitrites and nitrates. It The previously unknown, well-crystallizing nitrites or nitrates of the auramine dyes are formed in the process.
Man arbeitet zweckmäßig so, daß man das wasserlösliche Auraminsalz, z. B. das Hydrochlorid, bei etwa 50 bis 70° C in der erforderlichen Menge Wasser oder einem kleinen Überschuß an Wasser löst und ao dann die zur möglichst vollständigen Fällung des Farbstoffnitrits bzw. -nitrats erforderliche Menge eines wasserlöslichen Nitrits bzw. Nitrats, z. B. Natriumnitrit oder Kaliumnitrat, hinzufügt. Die erforderliche Menge läßt sich durch Vorversuche leicht ermitteln.It is expedient to work so that the water-soluble auramine salt, for. B. the hydrochloride about 50 to 70 ° C in the required amount of water or a small excess of water dissolves and ao then the amount required for the most complete possible precipitation of the dye nitrite or nitrate a water-soluble nitrite or nitrate, e.g. B. sodium nitrite or potassium nitrate, adds. The required The amount can easily be determined by preliminary tests.
Man kann die bei der technischen Herstellung von Auraminhydrochlorid durch Lösen der Schmelzen in Wasser erhaltenen Lösungen unmittelbar als Ausgangsmaterial verwenden. Man kann aus den Lösungen aber auch zunächst in üblicher Weise durch Zusatz von Natriumchlorid das Auraminhydrochlorid ausfällen und den abgesaugten Farbstoff vor oder nach dem Trocknen in Wasser lösen.The industrial production of auramine hydrochloride can be achieved by dissolving the melt in Use the solutions obtained in water immediately as starting material. One can from the Solutions, however, also initially in the usual way by adding sodium chloride to the auramine hydrochloride precipitate and dissolve the extracted dye in water before or after drying.
Die aus den Lösungen der Auraminhydrochloride durch Fällen mit wasserlöslichen Salzen von Stickstoffsauerstoffsäuren erhaltenen Salze sind wohl kristallisiert. Sie lösen sich überraschenderweise schon bei gewöhnlicher Temperatur sehr gut in Alkoholen, z. B. Methanol, Äthanol, Glykolen, Diäthylenglykol *° oder Diäthylenglykolmonoäthyläther, und in Lacken und eignen sich deshalb unter anderem vorzüglich zur Herstellung von Gummidruckfarben.The from the solutions of the auramine hydrochloride by precipitation with water-soluble salts of nitrogen oxygen acids salts obtained are probably crystallized. Surprisingly, they are already dissolving at ordinary temperature very well in alcohols, e.g. B. methanol, ethanol, glycols, diethylene glycol * ° or diethylene glycol monoethyl ether, and in paints and are therefore particularly suitable, among other things for the production of rubber printing inks.
Es war nicht ohne weiteres zu erwarten, daß die Salze der Auraminfarbstoffe, mit Stickstoffsäuren beständig sind und daß keine gegenseitige Oxydation und Reduktion zwischen Kation und Anion eintritt.It was not to be expected without further ado that the salts of the auramine dyes with nitric acids are stable and that there is no mutual oxidation and reduction between cation and anion.
Die neuen Auraminsalze enthalten praktisch keinen durch Metalle zu Schwefelwasserstoff reduzierbaren Schwefel, der den technischen Auraminhydrochloriden im allgemeinen von ihrer Herstellung her anhaftet. Anscheinend wird er durch die Anionen der Stickstoffsauerstoffsäuren oxydiert. Man kann daher Lacke, die mit den neuen Auraminsalzen gefärbt sind, z. B.The new auramine salts contain practically none that can be reducible to hydrogen sulfide by metals Sulfur, which generally adheres to technical auramine hydrochlorides from their manufacture. Apparently it is oxidized by the anions of the nitrogen oxygen acids. You can therefore paint, which are colored with the new auramine salts, e.g. B.
Verfahren zur HerstellungMethod of manufacture
von in Alkoholen gut löslichenof readily soluble in alcohols
Farbstoffen der AuraminreiheDyes of the auramine series
Anmelder:Applicant:
Badische Anilin- & Soda-FabrikAniline & Soda Factory in Baden
Aktiengesellschaft,Corporation,
Ludwigshafen/RheinLudwigshafen / Rhine
Dr. Fritz Schubert und Dr. Emil Kern,Dr. Fritz Schubert and Dr. Emil Kern,
Ludwigshafen/Rhein,
sind als Erfinder genannt wordenLudwigshafen / Rhine,
have been named as inventors
in verzinkten Kannen aufbewahren, ohne daß sie Schwefelwasserstoff entwickeln oder gleichzeitig anwesende, leicht reduzierbare Farbstoffe angreifen.keep in galvanized cans without evolving hydrogen sulphide or without being present at the same time attack easily reducible dyes.
Die in den Beispielen angegebenen Teile sind Gewichtsteile. The parts given in the examples are parts by weight.
5000 Teile einer gesättigten wäßrigen Lösung von AuramioiO (s·. Schultz, Farbstofftabelkm 1931, Nr. 752) werden bei 65° C unter Rühren mit 70 Teilen Natriumnitrat versetzt. Der neue Farbstoff fällt alsbald feinkristallin aus. Er wird nach dem Abkühlen auf 35° C abgesaugt und bei etwa 80° C getrocknet. Die Ausbeute beträgt 139 Teile. Der Farbstoff löst sich bereits in der Kälte im zehnfachen Gewicht Äthanol.5000 parts of a saturated aqueous solution of AuramioiO (see Schultz, Farbstofftabelkm 1931, no. 752) 70 parts of sodium nitrate are added at 65 ° C. with stirring. The new dye falls immediately finely crystalline. After cooling to 35 ° C, it is filtered off with suction and dried at about 80 ° C. The yield is 139 parts. The dye dissolves ten times its weight in the cold Ethanol.
An Stelle von Natriumnitrat kann man auch die äquivalente Menge Kalium-, Calcium- oder Ammoniumnitrat verwenden.Instead of sodium nitrate, you can also use the equivalent amount of potassium, calcium or ammonium nitrate use.
100 Teile Auramin G (Schultz, Farbstofftabellen 1931, Nr. 753) werden bei 25 bis 40° C in 8000 Teile Wasser eingerührt. Man erwärmt auf 70° C bis alles gelöst ist, und fügt dann 175 T2^ile--^atriumnitrat hinzu, wobei der neue Farbstoff caisbadii ausfällt. Man erhält 80 Teile eines in All^hol^ s4ljr gut löslichen Farbstoffes.100 parts of Auramin G (Schultz, Dye Tables 1931, No. 753) are converted into 8000 parts at 25 to 40 ° C Stir in water. The mixture is heated to 70 ° C. until everything has dissolved, and then 175 t 2 ^ ile - ^ atrium nitrate is added added, whereby the new dye caisbadii precipitates. 80 parts of one which is readily soluble in all-hol-s4ljr are obtained Dye.
Zu 5000 Teilen der im Beispiel 1 genannten Lösung von Auramin 0 gibt man bei 70° C unter Rühren 140 Teile Natriumnitrit. Der neue Farbstoff fällt als-5000 parts of the solution of auramine 0 mentioned in Example 1 are added at 70 ° C. with stirring 140 parts of sodium nitrite. The new dye falls as-
809 749i'328809 749i'328
bald in langen Nadeln aus. Er wird nach dem Abkühlen auf etwa 30° C abgesaugt und bei 80° C getrocknet. Die Ausbeute beträgt 141 Teile. Der Farbstoff löst sich sehr gut in Alkoholen.soon in long needles. He will after cooling Sucked off to about 30 ° C and dried at 80 ° C. The yield is 141 parts. The dye dissolves very well in alcohol.
50 Teile des im Beispiel 2 genannten Auramin G werden unter Rühren in 4000 Teilen Wasser bei 50 bis 60° C rasch gelöst und gegebenenfalls nitriert. Zu der Lösung gibt man sofort 40 Teile Natriumnitrit, wobei der neue Farbstoff kristallin ausfällt. Man läßt das Umsetzungsgemisch unter Rühren erkalten, saugt den Farbstoff ab und trocknet ihn. In guter Ausbeute erhält man einen Farbstoff, der in Alkoholen sehr gut löslich ist.50 parts of the auramine G mentioned in Example 2 are dissolved in 4000 parts of water at 50 with stirring Dissolved quickly up to 60 ° C and nitrated if necessary. to 40 parts of sodium nitrite are immediately added to the solution, the new dye precipitating in crystalline form. Man lets the reaction mixture cool with stirring, sucks off the dye and dries it. In good The yield is a dye which is very soluble in alcohols.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1050472B true DE1050472B (en) | 1959-02-12 |
Family
ID=590867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1050472D Pending DE1050472B (en) | Process for the preparation of highly soluble dyes of the auramm series in alcohols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1050472B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1109291B (en) | 1959-05-09 | 1961-06-22 | Basf Ag | Process for the production of dyes of the auramine series that are readily soluble in alcohols and alcohol-water mixtures |
| DE1127018B (en) | 1959-12-15 | 1962-04-05 | Basf Ag | Process for the production of dyes of the auramine series that are readily soluble in alcohols and alcohol-water mixtures |
-
0
- DE DENDAT1050472D patent/DE1050472B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1109291B (en) | 1959-05-09 | 1961-06-22 | Basf Ag | Process for the production of dyes of the auramine series that are readily soluble in alcohols and alcohol-water mixtures |
| DE1127018B (en) | 1959-12-15 | 1962-04-05 | Basf Ag | Process for the production of dyes of the auramine series that are readily soluble in alcohols and alcohol-water mixtures |
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