CH268432A - Process for the production of a new dye. - Google Patents
Process for the production of a new dye.Info
- Publication number
- CH268432A CH268432A CH268432DA CH268432A CH 268432 A CH268432 A CH 268432A CH 268432D A CH268432D A CH 268432DA CH 268432 A CH268432 A CH 268432A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- new dye
- production
- dianthrimide
- benzoylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 2
- 229940080299 sodium 2-naphthalenesulfonate Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- YWPOLRBWRRKLMW-UHFFFAOYSA-M sodium;naphthalene-2-sulfonate Chemical compound [Na+].C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 YWPOLRBWRRKLMW-UHFFFAOYSA-M 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- -1 sulfuric acid ester Chemical class 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KNVLCWQKYHCADB-UHFFFAOYSA-N chlorosulfonyloxymethane Chemical compound COS(Cl)(=O)=O KNVLCWQKYHCADB-UHFFFAOYSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- AOJBACHWNDMRQP-UHFFFAOYSA-N n,n-diethyl-4-methylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(C)C=C1 AOJBACHWNDMRQP-UHFFFAOYSA-N 0.000 description 1
- AFDQGRURHDVABZ-UHFFFAOYSA-N n,n-dimethylformamide;sulfur trioxide Chemical compound O=S(=O)=O.CN(C)C=O AFDQGRURHDVABZ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 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
- C09B9/00—Esters or ester-salts of leuco compounds of vat dyestuffs
- C09B9/02—Esters or ester-salts of leuco compounds of vat dyestuffs of anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 261976. Verfahren zur Herstellung eines neuen Farbstoffes. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines neuen Farbstoffes, welches dadurch gekennzeichnet ist, dass 5-Benzoylamino-1,1'-dianthrimid-2,2'- carbazol in Gegenwart eines von einem sekun dären Amin abgeleiteten organischen Amids mit einem Metall reduziert und zur Bildung des entsprechenden Leukoschwefelsäureesters mit einem Sulfatierungsmittel behandelt wird.
Der neue Farbstoff ist ein gelbbraunes Pulver, welches sich in Wasser unter Bildung einer gelbbraunen Lösung löst.
Als Beispiele von Amiden, die sieh für die obige Reaktion eignen, seien die von Carbon- säuren abgeleiteten Amide, beispielsweise Di- methylformamid, Diäthylformamid, Dimethyl- acetamid und Tetramethylharnstoff, und die von Sulfonsäuren abgeleiteten Amide, bei spielsweise N,N-Diäthyl-p-toluolsulfonamid, genannt. Man kann dem Reaktionsgemisch auch Verdünnungsmittel, wie z. B.
Aceton und Acetonitril, zusetzen. <I>Beispiel 1:</I> 5,4 Teile 5-Benzoylamino-1,1'-dianthrimid- 2,2'-rarbazol (welches durch Ringschluss aus 5-Benzoylamino-1,1'-dianthrimid erhalten wer den kann), 4 Teile Zinkpulver, 1 Teil Na- trium-2-naphthalinsulfonat und 40 Teile Di- methylformamid werden in einer inerten Atmosphäre während einer Stunde bei<B>170</B> C zusammengerührt.
Das durch Umsetzung von 21 Teilen Methylehlorsulfonat und 40 Teilen Dimethylformamid erhaltene Produkt wird zugesetzt und das Gemisch während 30 Minu ten bei 00 C gerührt. Es wird eine braune Lö sung erhalten, die eine grüne Fluoreszenz auf weist. Diese Lösung wird hierauf in 400 Teile einer wässerigen 10 o/oigen Natriumearbonat- lösung eingetragen. Das Gemisch wird filtriert und das Filtrat im Vakuum destilliert, bis sich im Destillierkolben Natriumsulfat. abzuschei den beginnt.
Hierauf versetzt man nach und nach mit Wasser, um das Volumen der Be- sehickung des Destillierkolbens konstant zu halten, und setzt die Destillation fort, bis etwa 500 Teile Wasser zugesetzt worden sind. Der Leukoschwefelsäureester wird hierauf ausge- salzt, abfiltriert, mit einer 10 o/oigen wässeri gen Natriumcarbonatlösung gewaschen, mit Dextrin vermischt und im Vakuum getrocknet.
<I>Beispiel 2:</I> 5,4 Teile 5-Benzoylamino-1,1'-dianthrimid- 2,2'-carbazol, 4 Teile Zinkstaub, 1 Teil Na- trium-2-naphthalinsulfonat und 40 Teile Di- methylformamid werden in einer inerten Atmosphäre während einer Stunde bei 170 C zusammengerührt.
Das Reaktionsgemisch wird bei 00 C in einer inerten Atmosphäre in 60 Teile einer gerührten Suspension von Di- methylformamid-Sehwefeltrioxyd in Dimethy l- formamid (mit einem Gehalt von 40 % Schwe- feltrioxyd) eingetragen.
Das Gemisch wird während 30 Minuten gerührt und der Leuko- schwefelsäureester in der in Beispiel 1 be schriebenen Weise isoliert. <I>Beispiel 3:</I> 5,4 Teile 5-Benzoylamino-1,1'-dianthrimid- 2,2'-carbazol, 4 Teile Zinkstaub, 1 Teil Methyl- triäthylammoniumchlorid, 40 Teile N-Formo- morpholid und 10 Teile Aceton werden wäh rend 5 Minuten bei 250 C gerührt.
Hierauf wird das durch Umsetzung von 40 Teilen Me- thylchlorsulfonat und 60 Teilen N-Formomor- pholid erhaltene Produkt zugesetzt und das auf diese Weise erhaltene Gemisch während 10 Minuten bei 00 C gerührt. Es wird eine braune Lösung mit einer grünen Fluoreszenz erhalten, aus welcher der Leukoschwefelsäure- ester in der in Beispiel 1 beschriebenen Weise isoliert wird.
<B> Additional patent </B> to the main patent No. 261976. Process for the production of a new dye. The present invention relates to a process for producing a new dye, which is characterized in that 5-benzoylamino-1,1'-dianthrimide-2,2'-carbazole in the presence of an organic amide derived from a secondary amine with a metal is reduced and treated with a sulfating agent to form the corresponding leuco sulfuric acid ester.
The new dye is a yellow-brown powder that dissolves in water to form a yellow-brown solution.
Examples of amides which are suitable for the above reaction are the amides derived from carboxylic acids, for example dimethylformamide, diethylformamide, dimethyl acetamide and tetramethylurea, and the amides derived from sulfonic acids, for example N, N-diethyl p-toluenesulfonamide, called. You can also diluents, such as. B.
Add acetone and acetonitrile. <I> Example 1: </I> 5.4 parts of 5-benzoylamino-1,1'-dianthrimide-2,2'-rarbazole (which can be obtained by ring closure from 5-benzoylamino-1,1'-dianthrimide ), 4 parts of zinc powder, 1 part of sodium 2-naphthalenesulfonate and 40 parts of dimethylformamide are stirred together in an inert atmosphere at 170 ° C. for one hour.
The product obtained by reacting 21 parts of methylehlorsulfonate and 40 parts of dimethylformamide is added and the mixture is stirred at 00 ° C. for 30 minutes. A brown solution is obtained which has a green fluorescence. This solution is then added to 400 parts of an aqueous 10% sodium carbonate solution. The mixture is filtered and the filtrate is distilled in vacuo until sodium sulfate appears in the still. begins to part.
Water is then added gradually to keep the volume of the stills in the still constant, and the distillation is continued until about 500 parts of water have been added. The leuco sulfuric acid ester is then salted out, filtered off, washed with a 10% strength aqueous sodium carbonate solution, mixed with dextrin and dried in vacuo.
<I> Example 2: </I> 5.4 parts of 5-benzoylamino-1,1'-dianthrimide-2,2'-carbazole, 4 parts of zinc dust, 1 part of sodium 2-naphthalene sulfonate and 40 parts of di- methylformamide are stirred together at 170 ° C. for one hour in an inert atmosphere.
The reaction mixture is introduced into 60 parts of a stirred suspension of dimethylformamide-sulfur trioxide in dimethylformamide (with a content of 40% sulfur trioxide) at 00 ° C. in an inert atmosphere.
The mixture is stirred for 30 minutes and the leuco-sulfuric acid ester is isolated in the manner described in Example 1. <I> Example 3: </I> 5.4 parts of 5-benzoylamino-1,1'-dianthrimide-2,2'-carbazole, 4 parts of zinc dust, 1 part of methyltriethylammonium chloride, 40 parts of N-formomorpholide and 10 parts of acetone are stirred at 250 ° C. for 5 minutes.
The product obtained by reacting 40 parts of methylchlorosulfonate and 60 parts of N-formomorpholide is then added and the mixture obtained in this way is stirred at 00 ° C. for 10 minutes. A brown solution with a green fluorescence is obtained, from which the leuco-sulfuric acid ester is isolated in the manner described in Example 1.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB268432X | 1946-11-22 | ||
| CH261976T | 1947-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH268432A true CH268432A (en) | 1950-05-15 |
Family
ID=25730522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH268432D CH268432A (en) | 1946-11-22 | 1947-11-21 | Process for the production of a new dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH268432A (en) |
-
1947
- 1947-11-21 CH CH268432D patent/CH268432A/en unknown
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