CH219585A - Process for the production of a vat dye of the anthraquinone series. - Google Patents
Process for the production of a vat dye of the anthraquinone series.Info
- Publication number
- CH219585A CH219585A CH219585DA CH219585A CH 219585 A CH219585 A CH 219585A CH 219585D A CH219585D A CH 219585DA CH 219585 A CH219585 A CH 219585A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone
- dye
- production
- vat
- weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 239000000984 vat dye Substances 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- NWFOTILLJRKQQH-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(Cl)=O)=C2[N+](=O)[O-] NWFOTILLJRKQQH-UHFFFAOYSA-N 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WBMPYOXBHLVYMK-UHFFFAOYSA-N 1-amino-10h-acridin-9-one Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N WBMPYOXBHLVYMK-UHFFFAOYSA-N 0.000 description 1
- -1 1-nitroanthraquinone-2-carboxylic acid halide Chemical class 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Nüpenfarbstoffes der Anthrachinonreihe. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines in blaustichigen Bordotönen färbenden Küpen- farbstoffes. Das Verfahren ist dadurch ge kennzeichnet,
dass man Anthrachino@n-2. 1-N- 1'. 2'-N-3'-chlor-6'-amiuobenzolakridon mit einem 1- Nitroanthrachinon - 2 - carbonsäure- halogenid umsetzt und die Nitrogruppe an schliessend durch Reduktion in die Amino- gruppe überführt. Die Umsetzung nimmt man vorteilhafterweise bei erhöhten Tempe raturen in Gegenwart eines inerten
Lösungs- mittels, wie zum Beispiel Nitrobenzol, vor. Die Reduktion des die Nitrogruppe enthal tenden Zwischenproduktes kann durch schwa che Reduktion beispielsweise durch Umküpen oder durch Reduktion in saurer, zum Beispiel in eiskalter schwefelsaurer Lösung mit einem Metallpulver ausgeführt werden.
Der gebil dete Farbstoff ist identisch mit demjenigen des Hauptpatentes. Er scheidet sich in vio letten Nadeln ab, die in organischen Lösungs- mitteln wenig löslich sind und aus' der stumpfvioletten Hydrosulfitküpe die Faser in chlor-, koch- und lichtechten, klaren blau stichigen Bordotönen anfärben. Im Rongalit- Pottaschedruck gibt .der feinverteilte Farb stoff auf Baumwolle und Kunstseide tiefe, klare Bordotöne von sehr guter Echtheit.
Beispiel: 80 Gewichtsteile Anthrachinon-2.1-N- 1' . 2'-N-3'. 6'-dichlorakridon, 70 Gewichts teile p-Toluolsulfamid, 20 Gewichtsteile ent wässertes Kaliumacetat, 700 Gewichtsteile Nitrobenzol und 2 Gewichtsteile Kupferacetat werden unter gutem Rühren 3 Stunden auf 205' erhitzt unter Abdestillieren der .gebildeten Es sigsäure. Man saugt die abgeschiedenen Kri stalle bei 55 C ab, wäscht mit Chlorbenzol, Al kohol und Wasser und trocknet.
Das Sulfamid bildet violette Nadeln. Zur Verseifung des selben werden 100 Gewichtsteile in 600 Ge wichtsteilen konzentrierter Schwefelsäure ge- löst und 1j2 Stunde auf 60 bis 70 C erhitzt; dann wird in Wasser ausgegossen, eine Stunde verrührt, abgesaugt, gewaschen und getrock net. Das Anthrachinon-2. 1-N-1' . 2'-N -3'- chlor-6'-aminobenzolakridon bildet blaue Na deln.
35 Gewichtsteile dieses Aminoakridons, 30 Gewichtsteile 1-Nitro-anthrachinon-2-car- bonsäurechlorid und 800 Gewichtsteile Nitro benzol werden eine Stunde unter Rühren auf 160 bis 170 C erhitzt. Das in vorzüglicher Ausbeute gebildete Zwischenprodukt wird noch heiss abgesaugt, mit warmem Chlorben zol und mit Alkohol gewaschen und getrock net.
Durch Umküpen führt. man die Nitro- gruppe in die Aminogruppe über und gelangt so zu einem Farbstoff, der violette Nadeln bildet, die in organischen Lösungsmitteln wenig löslich sind und aus der stumpfviolet ten Hydrosulfitküpe die Faser in chlor-, koch und lichtechten, klaren, blaustichigen Bordo- tönen anfärben. Im Rongalit-Pottaschedruck gibt der feinverteilte Farbstoff auf Baum- wolle und Kunstseide tiefe, klare Bordotöne von sehr guter Echtheit.
Die Reduktion kann auch in saurer, zum Beispiel in eiskalter, schwefelsaurer Lösung mit einem Metallpulver ausgeführt werden.
Process for the production of a nub dye of the anthraquinone series. The present invention relates to a process for the production of a vat dye which dyes in bluish drone shades. The procedure is characterized by
that one anthrachino @ n-2. 1-N- 1 '. 2'-N-3'-chloro-6'-amiuobenzolakridon is reacted with a 1-nitroanthraquinone-2-carboxylic acid halide and the nitro group is subsequently converted into the amino group by reduction. The reaction is advantageously carried out at elevated temperatures in the presence of an inert one
Solvent, such as nitrobenzene, before. The reduction of the intermediate product containing the nitro group can be carried out by weak reduction, for example by transferring or by reduction in acidic, for example in ice-cold, sulfuric acid solution with a metal powder.
The formed dye is identical to that of the main patent. It is deposited in violet needles that are sparingly soluble in organic solvents and dye the fibers from the dull violet hydrosulfite vat in clear blue-tinged bordo shades that are chlorine-, boil- and lightfast. In the Rongalit potash print, the finely distributed dye on cotton and rayon gives deep, clear bordo tones of very good fastness.
Example: 80 parts by weight of anthraquinone-2.1-N-1 '. 2'-N-3 '. 6'-dichloroacridone, 70 parts by weight of p-toluenesulfamide, 20 parts by weight of ent aqueous potassium acetate, 700 parts by weight of nitrobenzene and 2 parts by weight of copper acetate are heated to 205 'for 3 hours with thorough stirring while distilling off the acetic acid formed. The crystals which have separated out are filtered off with suction at 55 ° C., washed with chlorobenzene, alcohol and water and dried.
The sulfamide forms purple needles. To saponify the same, 100 parts by weight are dissolved in 600 parts by weight of concentrated sulfuric acid and heated to 60 to 70 ° C. for 1/2 hour; then it is poured into water, stirred for an hour, filtered off with suction, washed and dried. The anthraquinone-2. 1-N-1 '. 2'-N -3'-chloro-6'-aminobenzolakridon forms blue needles.
35 parts by weight of this aminoacridone, 30 parts by weight of 1-nitro-anthraquinone-2-carboxylic acid chloride and 800 parts by weight of nitrobenzene are heated to 160 to 170 ° C. for one hour with stirring. The intermediate product formed in excellent yield is filtered off with suction while it is still hot, washed with warm chlorobenzene and with alcohol and dried.
Leads through Umküpen. the nitro group is converted into the amino group and this leads to a dye that forms violet needles that are sparingly soluble in organic solvents and from the dull violet hydrosulphite vat the fibers in chlorine, boil and lightfast, clear, bluish Bordo tones stain. In Rongalit potash printing, the finely distributed dye gives the cotton and artificial silk deep, clear bordo tones of very good fastness.
The reduction can also be carried out in an acidic, for example in an ice-cold, sulfuric acid solution with a metal powder.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE219585X | 1937-09-04 | ||
| CH214907T | 1938-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH219585A true CH219585A (en) | 1942-02-15 |
Family
ID=25725657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH219585D CH219585A (en) | 1937-09-04 | 1938-08-29 | Process for the production of a vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH219585A (en) |
-
1938
- 1938-08-29 CH CH219585D patent/CH219585A/en unknown
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