CH210203A - Process for the preparation of an anthraquinone vat dye. - Google Patents
Process for the preparation of an anthraquinone vat dye.Info
- Publication number
- CH210203A CH210203A CH210203DA CH210203A CH 210203 A CH210203 A CH 210203A CH 210203D A CH210203D A CH 210203DA CH 210203 A CH210203 A CH 210203A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- brown
- vat dye
- anthraquinone vat
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 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 description 3
- 150000004056 anthraquinones Chemical class 0.000 title description 3
- 239000000984 vat dye Substances 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- -1 for example Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CEVURKAAFJXMHE-UHFFFAOYSA-N n-(8-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=12C(=O)C=3C(Cl)=CC=CC=3C(=O)C2=CC=CC=1NC(=O)C1=CC=CC=C1 CEVURKAAFJXMHE-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 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
- C09B5/26—Carbazoles of the anthracene series
- C09B5/28—Anthrimide carbazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonküpenfarbstoffes. Es wurde gefunden, dass ein wertvoller Anthrachinonküpenfarbs@toff hergestellt wer den kann, wenn man auf das Triantbrimid der Formel
EMI0001.0005
kondensierende Mittel einwirken lässt. Der neue Farbstoff ist ein braunes Pulver, das sich in Schwefelsäure mit gelboliver Farbe löst und Baumwolle aus brauner güpe in sehr echten, insbesondere sehr lichtechten Tönen rotbraun färbt.
Das als Ausgangsmaterial dienende Trianthrimid,der obigen Formel kann durch Erhitzen von 1 Mol 1,4-Diaminoanthrachinon mit 2 Mol 1-Chlor-8-benzoylaminoanthrachi- non in. Lösungs- oder Verdünnungsmitteln, wie zum Beispiel Nitrobenzol, Naphthalin oder Tetrahydronaphthalin, offen oder unter Druck, und zweckmässig in Anwesenheit von Katalysatoren,
wie Kupfer oder Kupferver- bindungen, sowie von säurebindenden Mit teln, wie zum Beispiel Alkalikarbonate und/oder entwässertem Natriumacetat, erhal ten werden.
Als kondensierende Mittel, die auf das Trianthrimid der obigen Formel einwirken gelassen werden, können die allgemein be kannten kondensierenden Mittel, die aus An- thrimiden Karbazolringe zu bilden vermögen, verwendet werden.
Solche kondensierende Mittel sind bekanntlich Schwefelsäure und deren Derivate, sowie besonders Aluminium- halogenide, wie zum Beispiel Aluminium chlorid, gegebenenfalls in Verbindung oder in Gegenwart von Alkalichloriden, wie zum Beispiel Natriumehlorid, von Schwefeldi oxyd, von Ammoniak, von organischen Ba sen wie zum Beispiel Pyridin, von Nitroben- zol, von Säurechloriden, wie zum Beispiel Benzoylehlorid, oder von Säurecyaniden, wie zum Beispiel Benzylcyanid.
Der erhaltene Farbstoff kann dadurch gereinigt werden, dass er mit oxydierenden Mitteln, wie zum Beispiel Alkalinitritlösung, in saurem Medium, A1li:alihypochloritlösi:iiic, oder Perboratlösung behandelt wird. Er lässt sich ferner nach bekannten Methoden in Leu koderivate, wie zum Beispiel in die Leuko- schwefelsäureester, überführen.
<I>Beispiel:</I> In eine Schmelze aus 120 Teilen Pyridin und 40 Teilen wasserfreiem Aluminiumchlo rid werden bei<B>100-150'</B> 20 Teile des Trian- thrimides der Formel
EMI0002.0020
eingetragen und eine Stunde auf 150-l60 erwärmt. Die Schmelze wird dann etwas ab kühlen gelassen und auf eine alkalische, 5() bis<B>60'</B> warme Hydrosulfitlösung, hergestellt aus 2000 Teilen Wasser, 250 Teilen 30 % ige Natronlauge und 50 Teilen Natriumhydro- sulfit, ausgetragen. Bei<B>50-60'</B> wird eine Viertelstunde gerührt und hierauf filtriert.
Die Leukoverbindung des Farbstoffes wird aus dem Filtrat durch Behandlung mit Luft, oxydiert und hierauf der erhaltene Farbstoff durch Filtration abgeschieden.
Process for the preparation of an anthraquinone vat dye. It has been found that a valuable anthraquinone vat dye can be produced using the triant brimide of the formula
EMI0001.0005
allows condensing agents to act. The new dye is a brown powder that dissolves in sulfuric acid with a yellow-olive color and dyes cotton from brown güpe in very real, especially very lightfast shades, red-brown.
The trianthrimide, of the above formula, which is used as starting material, can be prepared by heating 1 mole of 1,4-diaminoanthraquinone with 2 moles of 1-chloro-8-benzoylaminoanthraquinone in solvents or diluents, such as, for example, nitrobenzene, naphthalene or tetrahydronaphthalene, open or under pressure, and suitably in the presence of catalysts,
such as copper or copper compounds, as well as acid-binding agents such as alkali carbonates and / or dehydrated sodium acetate, can be obtained.
As condensing agents which are allowed to act on the trianthrimide of the above formula, the generally known condensing agents which are able to form carbazole rings from anthrimides can be used.
Such condensing agents are known to be sulfuric acid and its derivatives, and especially aluminum halides, such as aluminum chloride, optionally in combination or in the presence of alkali chlorides, such as sodium chloride, sulfur dioxide, ammonia, organic bases such as Pyridine, nitrobenzene, acid chlorides, such as benzyl chloride, or acid cyanides, such as benzyl cyanide.
The dye obtained can be purified by treating it with oxidizing agents, such as, for example, alkali metal nitrite solution, in an acidic medium, A1li: alihypochloritlösi: iiic, or perborate solution. It can also be converted into leuco derivatives, such as leuco sulfuric acid esters, using known methods.
<I> Example: </I> In a melt of 120 parts of pyridine and 40 parts of anhydrous aluminum chloride, at <B> 100-150 '</B>, 20 parts of the tranthhrimide of the formula
EMI0002.0020
entered and heated to 150-160 for one hour. The melt is then allowed to cool slightly and poured onto an alkaline, 5 () to <B> 60 '</B> warm hydrosulfite solution, prepared from 2000 parts of water, 250 parts of 30% strength sodium hydroxide solution and 50 parts of sodium hydrosulfite. At <B> 50-60 '</B> the mixture is stirred for a quarter of an hour and then filtered.
The leuco compound of the dye is oxidized from the filtrate by treatment with air and the dye obtained is then deposited by filtration.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH210203T | 1938-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210203A true CH210203A (en) | 1940-06-30 |
Family
ID=4446872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210203D CH210203A (en) | 1938-11-30 | 1938-11-30 | Process for the preparation of an anthraquinone vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210203A (en) |
-
1938
- 1938-11-30 CH CH210203D patent/CH210203A/en unknown
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