CH311501A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH311501A CH311501A CH311501DA CH311501A CH 311501 A CH311501 A CH 311501A CH 311501D A CH311501D A CH 311501DA CH 311501 A CH311501 A CH 311501A
- Authority
- CH
- Switzerland
- Prior art keywords
- aluminum chloride
- production
- carbazolating
- vat dye
- vat
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 5
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- -1 aluminum chloride-sodium chloride Chemical compound 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HYRQMUZVNDSZMA-UHFFFAOYSA-K [Al+3].[Cl-].[Cl-].[Cl-].O=S=O Chemical compound [Al+3].[Cl-].[Cl-].[Cl-].O=S=O HYRQMUZVNDSZMA-UHFFFAOYSA-K 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000002529 flux (metallurgy) Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C09B5/38—Compounds containing acridone and carbazole rings
-
- 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
- C09B5/26—Carbazoles of the anthracene series
- C09B5/28—Anthrimide carbazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 300336. Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Küpenfarbstoff gelangt, wenn man das Anthrimid der Formel
EMI0001.0005
mit carbazolierenden Mitteln behandelt.
Der neue Farbstoff färbt Baumwolle aus brauner Küpe in grünoliven Tönen.
Als carbazolierende Mittel kommen bei spielsweise Titantetrachlorid und insbesondere Aluminiumchlorid in Betracht. Die Reaktion kann in an sich bekannter Weise in Gegenwart passender Lösungs- bzw. Verdünnungs- oder Flussmittel durchgeführt werden, z.
B. in Ge genwart tertiärer Basen wie Chinolin oder 1'y ridin, von Nitrobenzol, mit Hilfe der be kannten Schwefeldioxyd-Aluminiumchlorid- Additionsprodukte. Als besonders zweckmässig erweist sich die Carbazolierung mit Alumi- niumchlorid-1Vatriumchlorid oder mit Alumi niumchlorid in technischen ss,y-Picolingemisch. Gute Ergebnisse werden in der Regel dann erzielt, wenn man die Carbazolierung bei ver hältnismässig hohen Temperaturen, z.
B. bei <B>1.60</B> bis 180 , ausführt, was mit den beiden zuletzt erwähnten Carbazolierungsmitteln ohne weiteres möglich ist. <I>Beispiel:</I> 2,5 Teile 4,4'-Dibrom-1,1'-dianthrimid, 3,2 Teile 5'-Chlor-4-amino-1(N),2,2'(N),1'- anthrachinonbenzolacridon, 0,8 Teile Natrium acetat, 0,3 Teile Kupfer(II)acetat und 300 Teile Nitrobenzol werden 7 Stunden zum Sieden erhitzt. Nach dem Erkalten wird ab gesaugt, mit Nitrobenzol, dann Alkohol aus gewaschen und in üblicher Weise gereinigt. Man erhält das Anthrimid in Form eines dunkel gefärbten Pulvers.
1 Teil desselben wird in einer Schmelze von 30 Teilen Aluminiumchlorid und 6 Teilen Natriumchlorid 1 Stunde auf 160 bis 1650 er hitzt. Man giesst sodann auf Eis aus und fil triert. Der Rückstand wird ausgewaschen und in stark verdünnter Schwefelsäure suspen diert. Nach Zusatz von 0,3 Teilen Natrium- bichromat lässt man 5 bis 6 Stunden bei Zim mertemperatur rühren, filtriert hierauf wie der und wäscht gründlich mit Wasser aus. Der so erhaltene Farbstoff kann in Pulver- oder Pastenform zur Verwendung gelangen.
Additional patent to main patent no. 300336. Process for the production of a vat dye. It has been found that a valuable vat dye is obtained by using the anthrimide of the formula
EMI0001.0005
treated with carbazolating agents.
The new dye dyes cotton from a brown vat in green-olive tones.
Suitable carbazolating agents are, for example, titanium tetrachloride and, in particular, aluminum chloride. The reaction can be carried out in a manner known per se in the presence of suitable solvents, diluents or fluxes, eg.
B. in Ge present tertiary bases such as quinoline or 1'y ridin, from nitrobenzene, with the help of the known sulfur dioxide-aluminum chloride addition products. Carbazolation with aluminum chloride-1-sodium chloride or with aluminum chloride in a technical γ-picolin mixture has proven to be particularly useful. Good results are usually achieved if the carbazolation is carried out at relatively high temperatures, e.g.
B. at <B> 1.60 </B> to 180, which is easily possible with the two last-mentioned carbazolating agents. <I> Example: </I> 2.5 parts 4,4'-dibromo-1,1'-dianthrimide, 3.2 parts 5'-chloro-4-amino-1 (N), 2.2 '( N), 1'-anthraquinone benzene acridone, 0.8 part of sodium acetate, 0.3 part of copper (II) acetate and 300 parts of nitrobenzene are heated to the boil for 7 hours. After cooling, it is filtered off with suction, washed off with nitrobenzene and then with alcohol and cleaned in the usual way. The anthrimide is obtained in the form of a dark-colored powder.
1 part of the same is heated in a melt of 30 parts of aluminum chloride and 6 parts of sodium chloride for 1 hour to 160 to 1650. It is then poured onto ice and filtered. The residue is washed out and suspended in very dilute sulfuric acid. After adding 0.3 part of sodium bichromate, the mixture is stirred for 5 to 6 hours at room temperature, then filtered again and washed thoroughly with water. The dye thus obtained can be used in powder or paste form.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311501T | 1952-10-21 | ||
| CH300336T | 1952-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311501A true CH311501A (en) | 1955-11-30 |
Family
ID=25734248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311501D CH311501A (en) | 1952-10-21 | 1952-10-21 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311501A (en) |
-
1952
- 1952-10-21 CH CH311501D patent/CH311501A/en unknown
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