CH274720A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH274720A CH274720A CH274720DA CH274720A CH 274720 A CH274720 A CH 274720A CH 274720D A CH274720D A CH 274720DA CH 274720 A CH274720 A CH 274720A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- production
- vat
- carboxylic acid
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000001044 red dye Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- XVZJIUCKFLHADT-UHFFFAOYSA-N 1-amino-6-chloro-4-nitroanthracene-9,10-dione Chemical compound NC1=CC=C(C=2C(C3=CC(=CC=C3C(C12)=O)Cl)=O)[N+](=O)[O-] XVZJIUCKFLHADT-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IMBDOWRCAFRQFG-UHFFFAOYSA-N NC(C(C(C1=CC(Cl)=CC=C11)=O)=C2C1=O)=CC=C2NC(C(C=CC=C1)=C1F)=O Chemical compound NC(C(C(C1=CC(Cl)=CC=C11)=O)=C2C1=O)=CC=C2NC(C(C=CC=C1)=C1F)=O IMBDOWRCAFRQFG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man 1- (2'-Fluorbenzoylamino) -4-amino-6- cliloranthraehinon mit einem reaktionsfähigen funktionellen Derivat der 3-Methylsulfonben- zal-l-carbonsäure acyliert.
Der nette Farbstoff bildet rote Kristalle, die sich in konz. Schwefelsäure mit roter Farbe lösen, und färbt Baumwolle aus violet ter Küpe in sehr echten, blaustichigen Ross- tönen, Das als Ausgangsstoff für das vorliegende Verfahren verwendete 1- (2'-Fluorbenzoyl- amino)
-4-amino-6-chloranthrachinon kann bei spielsweise durch Acylierung von 1-Amino-4- nitro-6-chloranthrachinon mit 2-Fluor-l-ben- zoylchlorid und nachträgliche Reduktion der Nitrogruppe nach den üblichen Methoden her gestellt werden. Die Verbindung kristallisiert <B> < </B> itus o-Dichlorbenzol in violetten Kriställchen.
Als reaktionsfähige funktionelle Derivate der 3-Methylsulfonbenzoll-carbonsäure kön nen für das vorliegende Verfahren zweck mässig die Säurehalogenide, insbesondere das Säurechlorid, verwendet werden. Die Umset zung .der Aminoanthrachinonkomponente mit der Säurekoiriponente kann in an sich bekann ter Weise, zweckmässig in hochsiedenden Lösungsmitteln, wie Chlorbenzol, Dichlorben- zol, Nitrobenzol oder Naphthalin, bei erhöh ten Temperaturen durchgeführt werden.
Beispiel: 11 Teile. 3-Methylsulfonbenzol-l-carbon- säure werden in 324 Teilen trockenem Nitro- benzol suspendiert und nach Zufügen von F Teilen Thionylchlorid und 0,5 Teilen Pyri- din anderthalb Stunden bei 90 bis 1000 ver rührt. Hierauf werden 19,7 Teile 1-(2'-Fluor- benzoylamino) -4- amino- 6 - chloranthrachinon zugefügt.
Nachdem noch zwei Stunden bei 125 bis 1300 weitergerührt wurde, wird erkal- tengelassen und der in roten Kriställchen ausfallende Farbstoff abgesaugt, gut mit Nitrobenzol und kochendem Alkohol gewa schen und getrocknet,
Process for the production of a vat dye. It has been found that a valuable vat dye can be prepared if 1- (2'-fluorobenzoylamino) -4-amino-6-cliloranthraehinone is acylated with a reactive functional derivative of 3-methylsulfonbenzal-1-carboxylic acid.
The nice dye forms red crystals, which are in conc. Dissolve sulfuric acid with red color, and dyes cotton from a purple vat in very real, bluish shades of pink. The 1- (2'-fluorobenzoylamino) used as the starting material for the present process
-4-amino-6-chloroanthraquinone can for example be made by acylation of 1-amino-4-nitro-6-chloroanthraquinone with 2-fluoro-1-benzoyl chloride and subsequent reduction of the nitro group by the usual methods. The compound crystallizes <B> <</B> itus o-dichlorobenzene in purple crystals.
The acid halides, in particular the acid chloride, can advantageously be used as reactive functional derivatives of 3-methylsulfonbenzene carboxylic acid for the present process. The reaction of the aminoanthraquinone component with the acid component can be carried out in a manner known per se, expediently in high-boiling solvents such as chlorobenzene, dichlorobenzene, nitrobenzene or naphthalene, at elevated temperatures.
Example: 11 parts. 3-Methylsulfonbenzene-1-carboxylic acid are suspended in 324 parts of dry nitrobenzene and, after F parts of thionyl chloride and 0.5 part of pyridine have been added, the mixture is stirred at 90 to 1000 for one and a half hours. 19.7 parts of 1- (2'-fluoro-benzoylamino) -4-amino-6-chloroanthraquinone are then added.
After stirring for a further two hours at 125 to 1300, it is allowed to cool and the dye which precipitates out in red crystals is suctioned off, washed well with nitrobenzene and boiling alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH272571T | 1947-07-17 | ||
| CH274720T | 1948-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH274720A true CH274720A (en) | 1951-04-15 |
Family
ID=25731389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH274720D CH274720A (en) | 1947-07-17 | 1948-05-13 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH274720A (en) |
-
1948
- 1948-05-13 CH CH274720D patent/CH274720A/en unknown
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