CH268430A - Process for the production of a new dye. - Google Patents
Process for the production of a new dye.Info
- Publication number
- CH268430A CH268430A CH268430DA CH268430A CH 268430 A CH268430 A CH 268430A CH 268430D A CH268430D A CH 268430DA CH 268430 A CH268430 A CH 268430A
- Authority
- CH
- Switzerland
- Prior art keywords
- new dye
- production
- parts
- brown
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 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
- 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 238000004043 dyeing Methods 0.000 description 1
- 239000000463 material 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
- WBGWGHYJIFOATF-UHFFFAOYSA-M potassium;methyl sulfate Chemical compound [K+].COS([O-])(=O)=O WBGWGHYJIFOATF-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004753 textile 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
- 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
Zusatzpatent 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 4,4',4"-Tribeiizoylamino-1,1',g,1"-tri- anthrimid-2,2',7,2"-dicarbazol in Gegenwart eines von einem sekundären Amin abgeleiteten organischen Amids mit einem Metall reduziert und zur Bildung des entsprechenden Leuko- schwefelsäureesters mit einem Sulfatierungs- mittel. behandelt wird.
Der neue Farbstoff ist ein braunes Pulver, welches sich in Wasser unter Bildung einer braunen Lösung löst.
Als Beispiele von Amiden, die sich für die obige Reaktion eignen, seien die von Carbon- säuren abgeleiteten Amide, beispielsweise Di- metliylformamid, 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:</I> 70 Teile Dimethylformamid werden mit 5 Teilen 4,4',4"-Tribenzoylamino-1,1',8,1"-tri- azithrimid-2,2',7,2"-dicarbazol (welches durch Ringschluss aus 4,4',4"-Tribenzoylamino-1,1', 8,1"-trianthrimid erhalten werden kann), 3 Teilen Zinkstaub und 1 Teil Kaliummethyl- sulfat versetzt.
Das Reaktionsgemisch wird in einer inerten Atmosphäre während 30 Minuten bei 600 C gerührt und darin auf 00 C abge- kühlt. 60 Teile einer Lösung von Dimethyl- formamid-Schwefeltrioxyd in Dimethylform- ainid, die 10 Teilen Schwefeltrioxyd entspre- ehen, werden hierauf zugesetzt, worauf das Gemisch während 30 Minuten in einem Eisbad gerührt und gekühlt wird.
Das Gemisch wird hierauf in eine Lösung von 15 Teilen Na- triumcarbonat in 300 Teilen Wasser eingetra gen, und die Metallrückstände werden durch Filtrieren. entfernt. Der Leukoschwefelsäure- ester wird durch Destillation im Vakuum und durch Aussalzen isoliert. Das Produkt wird abfiltriert und im Vakuum getrocknet.
Das Produkt löst sich in Wasser unter Bildung einer braunen Lösung und kann naciz den üblichen Verfahren des Färbens, Aufklot- zens und Druckens auf Textilmaterialien auf getragen werden, wobei echte braune Farbtöne entstehen.
Additional patent to main patent No. 261976. Process for the production of a new dye. The present invention relates to a process for the production of a new dye, which is characterized in that 4,4 ', 4 "-tribeiizoylamino-1,1', g, 1" -tri-anthrimide-2,2 ', 7, 2 "-dicarbazole is reduced with a metal in the presence of an organic amide derived from a secondary amine 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 brown solution.
Examples of amides that 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: </I> 70 parts of dimethylformamide are mixed with 5 parts of 4,4 ', 4 "-tribenzoylamino-1,1', 8,1" -tri- azithrimid-2,2 ', 7,2 "- dicarbazole (which can be obtained by ring closure from 4,4 ', 4 "-tribenzoylamino-1,1', 8.1" -trianthrimide), 3 parts of zinc dust and 1 part of potassium methyl sulfate are added.
The reaction mixture is stirred in an inert atmosphere for 30 minutes at 600.degree. C. and then cooled to 00.degree. 60 parts of a solution of dimethylformamide sulfur trioxide in dimethylformamide, which corresponds to 10 parts of sulfur trioxide, are then added, whereupon the mixture is stirred and cooled in an ice bath for 30 minutes.
The mixture is then introduced into a solution of 15 parts of sodium carbonate in 300 parts of water, and the metal residues are filtered off. away. The leuco sulfuric acid ester is isolated by distillation in vacuo and by salting out. The product is filtered off and dried in vacuo.
The product dissolves in water to form a brown solution and can be applied to textile materials using the usual methods of dyeing, padding and printing, producing real brown shades.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB268430X | 1946-11-22 | ||
| CH261976T | 1947-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH268430A true CH268430A (en) | 1950-05-15 |
Family
ID=25730520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH268430D CH268430A (en) | 1946-11-22 | 1947-11-21 | Process for the production of a new dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH268430A (en) |
-
1947
- 1947-11-21 CH CH268430D patent/CH268430A/en unknown
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