CH261976A - Process for the production of a new dye. - Google Patents
Process for the production of a new dye.Info
- Publication number
- CH261976A CH261976A CH261976DA CH261976A CH 261976 A CH261976 A CH 261976A CH 261976D A CH261976D A CH 261976DA CH 261976 A CH261976 A CH 261976A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- new dye
- production
- acid ester
- sulfuric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- -1 sulfuric acid ester Chemical class 0.000 claims description 2
- 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 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- KNVLCWQKYHCADB-UHFFFAOYSA-N chlorosulfonyloxymethane Chemical compound COS(Cl)(=O)=O KNVLCWQKYHCADB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 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
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 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
- 230000004523 agglutinating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 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
- 238000002360 preparation method Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 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
- 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)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Farbstoffes. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines neuen Farbstoffes, welches dadurch gekennzeichnet ist, dass 4,5'-Dibenzoylamino-1,1'-dianthrimid- 2,2'-carbazol in Gegenwart eines von einem sekundären Amin abgeleiteten organischen Amids mit einem Metall reduziert und zur Bildung des entsprechenden Leukoschwefel- säureesters mit einem Sulfatierungsmittel be handelt wird.
Der neue Farbstoff ist ein braunes Pulver, welches sich in Wasser unter Bildung einer gelben Lösung löst.
Als Beispiele von Amiden, die sich 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 Verdünnungsmittel, wie z. B.
Aceton und Acetonitril, zusetzen. <I>Beispiel 1:</I> <B>15,5</B> Teile Methy lehlorsulfonat werden unter Rühren und Kühlen in ein Gemisch von 20 Teilen Dimethylformamid und 16 Teilen Aceton eingetragen.
Die auf diese Weise ge bildete Lösung von Dimethylformamid-Schwe- feltrioxyd wird mit 6,65 Teilen 4,5'-Dibenzoyl- amino-1,1'-dianthrimid-2,2'-carbazol (welches durch Ringschluss aus 4,5' - Dibenzoylamino- 1,1'-dianthrimid erhalten werden kann) in fein verteilter Form und hierauf mit 2,7 Tei len fein verteiltem Eisenpulver versetzt.
Das Gemisch wird während 21/2 Stunden bei 15-20 C gerührt und hierauf in 260 Teile einer 5 % igen Natriumcarbonatlösung einge tragen. Die Metallrückstände werden durch Filtration abgetrennt und die Filtrate im Va kuum destilliert, um Dimethylformamid zu entfernen und die wässrige Lösung zu konzen trieren.
Der Leukoschwefelsäureester wird mit Natriumchlorid ausgesalzen und kann in Ge genwart von Natriumcarbonat und eines dis pergierenden Mittels oder eines agglutinieren- den Mittels getrocknet werden. Er löst sich leicht in Wasser unter Bildung einer gelben Lösung. Beim Färben, Aufklotzen oder Auf drucken auf Stoffe in der üblichen Weise er zeugt der Leukoschwefelsäureester braune Farbtöne mit guten Echtheitseigenschaften.
<I>Beispiel 2:</I> 11,2 Teile a-Picolin werden dem Reaktions produkt aus 60 Teilen Dimethylformamid und 15,5 Teilen Methylchlorsulfonat zugesetzt. Dieses Gemisch wird mit 6,65 Teilen des in Beispiel 1 verwendeten Farbstoffes und 4 Tei len Eisenpulver versetzt. Das Gemisch wird innert 1/2 Stunde auf 50 C erhitzt und wäh rend 4 Stunden bei 50 C gerührt. Das Reak tionsgemisch wird in 300 Teile eines Gemi sches aus Eis und Wasser, welches 16 Teile Natriumcarbonat enthält, eingetragen und der Leukoschwefelsäureester in der in Beispiel 1 beschriebenen Weise isoliert.
Process for the production of a new dye. The present invention relates to a process for the preparation of a new dye which is characterized in that 4,5'-dibenzoylamino-1,1'-dianthrimide-2,2'-carbazole in the presence of an organic amide derived from a secondary amine with a metal and treated with a sulfating agent to form the corresponding leuco-sulfuric acid ester.
The new dye is a brown powder that dissolves in water to form a yellow solution.
Examples of amides which are suitable for the above reaction are the amides derived from carboxylic acids, for example dimethylformamide, diethylformamide, dimethylacetamide and tetramethylurea, and the amides derived from sulfonic acids, for example N, N-diethyl p-toluenesulfonamide, called. You can add diluents to the reaction mixture, such as. B.
Add acetone and acetonitrile. <I> Example 1: </I> <B> 15.5 </B> parts of methyl chlorosulfonate are introduced into a mixture of 20 parts of dimethylformamide and 16 parts of acetone with stirring and cooling.
The solution of dimethylformamide-sulfur trioxide formed in this way is mixed with 6.65 parts of 4,5'-dibenzoylamino-1,1'-dianthrimide-2,2'-carbazole (which by ring closure from 4,5 ' - Dibenzoylamino-1,1'-dianthrimide can be obtained) in finely divided form and then treated with 2.7 parts of finely divided iron powder.
The mixture is stirred for 21/2 hours at 15-20 ° C. and then added to 260 parts of a 5% sodium carbonate solution. The metal residues are separated off by filtration and the filtrates are distilled in vacuo in order to remove dimethylformamide and to concentrate the aqueous solution.
The leuco sulfuric acid ester is salted out with sodium chloride and can be dried in the presence of sodium carbonate and a dispersing agent or an agglutinating agent. It dissolves easily in water to form a yellow solution. When dyeing, padding or printing on fabrics in the usual way, the leuco-sulfuric acid ester produces brown shades with good fastness properties.
Example 2: 11.2 parts of a-picoline are added to the reaction product composed of 60 parts of dimethylformamide and 15.5 parts of methylchlorosulfonate. This mixture is mixed with 6.65 parts of the dye used in Example 1 and 4 Tei len iron powder. The mixture is heated to 50 ° C. within 1/2 hour and stirred at 50 ° C. for 4 hours. The reaction mixture is added to 300 parts of a Gemi cal of ice and water which contains 16 parts of sodium carbonate, and the leuco-sulfuric acid ester is isolated in the manner described in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB261976X | 1946-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261976A true CH261976A (en) | 1949-06-15 |
Family
ID=10239877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261976D CH261976A (en) | 1946-11-22 | 1947-11-21 | Process for the production of a new dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261976A (en) |
-
1947
- 1947-11-21 CH CH261976D patent/CH261976A/en unknown
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