DE659592C - Process for the preparation of dyes of the fluorindine series - Google Patents
Process for the preparation of dyes of the fluorindine seriesInfo
- Publication number
- DE659592C DE659592C DEI47741D DEI0047741D DE659592C DE 659592 C DE659592 C DE 659592C DE I47741 D DEI47741 D DE I47741D DE I0047741 D DEI0047741 D DE I0047741D DE 659592 C DE659592 C DE 659592C
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- fluorindine
- series
- preparation
- weight
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- IDDYUZBZSSUAGK-UHFFFAOYSA-N 1-n,4-n-diphenyl-3,6-bis(phenylimino)cyclohexa-1,4-diene-1,4-diamine Chemical class C=1C=CC=CC=1NC(C(C=C1NC=2C=CC=CC=2)=NC=2C=CC=CC=2)=CC1=NC1=CC=CC=C1 IDDYUZBZSSUAGK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims 1
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical class C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- -1 pyrene radical Chemical class 0.000 description 1
- 239000000725 suspension 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
- C09B17/06—Fluorindine or its derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Farbstoffen der Fluorindinreihe Es wurde gefunden, daß man Farbstoffe der Fluorindinreihe mit guten Echtheitsegenschaften, welche licht- und waschechte Färbungen von großer Intensität liefern, erhalten kann, wenn man Azopheninverbindungen, die aus Aminopyrenen und p-Chinondianilen nach bekannten Verfahren ierhältlich sind, mit oxydierenden Mitteln behandelt. Es war überraschend, daß sich Azopheninverbindungen, die ,als Arylradikale den Pyrenrest enthalten, überhaupt zu Fluorindinverbindungen kondensiert werden konnten. Die Farbstoffe können, falls gewünscht, halogeniert werden. Die neuen Verbindungen sollen entweder nach ihrer Sulfierung zum Anfärben von Fasern oder unsulfiert als Lackfarbstoffe Verwendung finden. Beispiele i. i,5 Gewichtsteile 3-Aminopyren (F. 117') werden in 2o Gewichtsteilen Eisessig suspendiert. Diese Suspension wird mit 3 Gewichtsteilen p-Cbinondianil versetzt und i Stunde lang auf i i o° erhitzt. Nach dem Abkühlen auf etwa 70° werden io Gewichtsbeile Alkohol hinzugegeben und das entstandene Riaktionsprodukt abfiltriert. Durch Auskochen mit Alkohol wird ihm das bei der Reaktion mitentstandene Diphenyl-p-phenylendiamin entzogen. Das Reaktionsprodukt bildet kleine schwarze Kristalle, die sich violett in konzentrierter Schwefelsäure lösen.Process for the preparation of dyes of the fluorindine series Es was found that dyes of the fluorine indine series with good fastness properties, which can provide and obtain lightfast and washfast colors of great intensity, when one azophenine compounds, which are made from aminopyrenes and p-quinondianils according to known Processes are available, treated with oxidizing agents. It was surprising that azophenine compounds, which contain the pyrene radical as aryl radicals, are at all could be condensed to fluoroindine compounds. The dyes can, if desired to be halogenated. The new connections should either be after their Sulphation for dyeing fibers or unsulphurised as lacquer dyes Find. Examples i. 1.5 parts by weight of 3-aminopyrene (F. 117 ') are used in 2o parts by weight Glacial acetic acid suspended. This suspension is made with 3 parts by weight of p-Cbinondianil added and heated to 10 ° for 1 hour. After cooling down to about 70 ° 10 parts by weight of alcohol are added and the reaction product formed is filtered off. By boiling with alcohol, the diphenyl-p-phenylenediamine, which was also formed during the reaction, is given to him withdrawn. The reaction product forms small black crystals that turn purple dissolve in concentrated sulfuric acid.
Ein Gewichtsteil des so erhaltenen Produktes wird in 15 Gewichtsteilen a-Chlornaphthalin ;gelöst und in der Hitze mit o,9 Gewichtsteilen Bleidioxyd versetzt und 30 Minuten gekocht. Die Lösung ist dann blau geworden, wird von den Bleioxyden abfiltriert und scheidet beim Erkalten das Fluorindin in kleinen Kristallen ab; die sich in konzentrierter Schwefelsäure grün lösen. Wird das Fluorindin in Monohydrat gelöst und so viel 2oprozentiges Oleum hinzuglegeben, daß der SO.-Gehalt etwa 5 % beträgt, so tritt leicht Sulfierung ein. Das sulfierte Fluorindin zieht mit grüner Farbe auf Baumwolle. Die Färbungen zeichnen sich durch große Lichtechtheit aus. Durch Zusatz von Brom zu der @obengenannten Sulfierungslösung findet sofort Bnomierung des Farbstoffes, statt.One part by weight of the product thus obtained is dissolved in 15 parts by weight of α-chloronaphthalene, 0.9 parts by weight of lead dioxide are added while hot and the mixture is boiled for 30 minutes. The solution has then turned blue, is filtered off from the lead oxides and, on cooling, separates the fluorine indine in small crystals; which dissolve green in concentrated sulfuric acid. If the fluorine indine is dissolved in monohydrate and so much 2% oleum is added that the SO content is about 5%, sulphonation occurs easily. The sulfated fluorine indine is green on cotton. The dyeings are characterized by great lightfastness. By adding bromine to the above-mentioned sulphonation solution, naming of the dye takes place immediately.
2. i Gewichtsbeil dies nach Beispiel i hergestellten Fluorindins wird in io Gewichtsteilen 2oprozentigeni Oleum gelöst und i/2 Stunde auf ioo° erhitzt. Man erhält eine Sulfosäure, die in grauen lichtechten Tönen auf die Baumwolle zieht.2. i part by weight of this fluorindine prepared according to example i dissolved in 10 parts by weight of 2% strength oleum and heated to 100 ° for 1/2 hour. A sulfonic acid is obtained which is absorbed in the cotton in gray, lightfast shades.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI47741D DE659592C (en) | 1933-08-12 | 1933-08-12 | Process for the preparation of dyes of the fluorindine series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI47741D DE659592C (en) | 1933-08-12 | 1933-08-12 | Process for the preparation of dyes of the fluorindine series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE659592C true DE659592C (en) | 1938-05-06 |
Family
ID=7192073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI47741D Expired DE659592C (en) | 1933-08-12 | 1933-08-12 | Process for the preparation of dyes of the fluorindine series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE659592C (en) |
-
1933
- 1933-08-12 DE DEI47741D patent/DE659592C/en not_active Expired
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