CH100190A - Process for the preparation of a sulfur-containing cotton dye. - Google Patents
Process for the preparation of a sulfur-containing cotton dye.Info
- Publication number
- CH100190A CH100190A CH100190DA CH100190A CH 100190 A CH100190 A CH 100190A CH 100190D A CH100190D A CH 100190DA CH 100190 A CH100190 A CH 100190A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfur
- preparation
- dye
- containing cotton
- solution
- Prior art date
Links
- 229920000742 Cotton Polymers 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000011593 sulfur Substances 0.000 title claims description 4
- 229910052717 sulfur Inorganic materials 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 11
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 4
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000004057 1,4-benzoquinones Chemical class 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- -1 Aminoaryl mercaptans Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- DVSIMTIVFCIAIP-UHFFFAOYSA-N 2-aminobenzenethiol;zinc Chemical compound [Zn].NC1=CC=CC=C1S DVSIMTIVFCIAIP-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NGDNCZPCIZNCQS-UHFFFAOYSA-N ctk3j8699 Chemical compound Cl=S NGDNCZPCIZNCQS-UHFFFAOYSA-N 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-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
- C09B49/00—Sulfur dyes
- C09B49/10—Sulfur dyes from diphenylamines, indamines, or indophenols, e.g. p-aminophenols or leucoindophenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Baumwollfarbstoffes. Die Erfindung beruht auf der Beobach tung, dass Arylchinone, insbesondere haloge- nierte Benzochinone, sich mit o . Aminoaryl- merkaptanen kondensieren und dass die so gewonnenen Kondensationsprodukte beim Be handeln mit den üblichen Schwefelungsmit- teln in höher geschwefelte Körper übergehen.
welche Baumwolle im Schwefelnatriumbade oder in der Hydrosulfitküpe echt anfärben. Das o. Aminoarylmerkaptan kann als solches oder in Form einer äquivalenten Verbindung verwandt werden, welche im' Laufe der Re aktion ein o. Aminoarylmerkaptan erzeugt, zum Beispiel also in Form eines o . o . Dini- tro- oder o . o . Diaminodiaryldisulfids, einer o. Aminoarylthiosulfosäure, eines Einwir kungsproduktes von Chlorschwefel auf einen aromatischen Aminokörper (siehe Schweizer Patent Nr.
71331 und Zusätze) oder einer der Verbindungen, welche aus diesen Ein wirkungsprodukten durch die Einwirkung von Wasser und iXlkalien (siehe Schweizer Patent Nr. 72277 und Zusätze) entstehen.
Das vorliegende Patent hat nun ein Ver fahren zur Darstellung eines solchen schwe- felhaltigen Baumwollfarbstoffes zum Gegen stand. Das Verfahren beruht darauf, dass ein halogeniertes Benzochinon mit o. Amino- thiophenol kondensiert und das so gebildete Kondensationsprodukt mit den üblichen Schwefelungsmitteln weiter geschwefelt wird. Es kann auch ein solcher Ausgangsstoff ver wendet werden, aus welchem o . Aminothio- phenol intermediär entsteht. Der neue Farb stoff färbt Baumwolle im Schwefelnatrium bade oder aus der Küpe direkt rotbraun.
Die Färbungen sind durch gute Echtheiten, ins besondere durch eine bemerkenswerte Chlor echtheit, ausgezeichnet.
<I>Beispiel:</I> 25 kg Chloranil (oder die äquivalente Menge Di- oder Trichlorchinon) und 12,5 kg o . Aminothiophenol (oder die äquivalente Menge o. Aminothiophenolchlorhydrat, oder o. Aminothiophenolzinkmerkaptid) werden mit der ungefähr zwanzigfachen Menge Was ser, Alkohol oder Eisessig angerührt und im geeigneten Gefäss mehrere Stunden unter gutem Rühren gekocht. Es ist vorteilhaft, eine der freiwerdenden Salzsäure entsprechende Menge Natrium acetat zuzufügen.
Nach beendeter Reaktion ist das kronden- sationsprodukt in Form eines violettblauen, kristallinischen Pulvers fast ausgeschieden; dasselbe wird abfiltriert.
20 kg des so erhaltenen Kondensations produktes werden in eine PolSsulfidlösung- eingetragen, welche durch Erhitzen von 40 kg Schwefelnatrium krist., 25 kg Schwefel in etwa 100 Liter Wasser hergestellt ist. Man kocht das Ganze längere Zeit, etwa 60 Stunden, unter Rückfluss, verdünnt dann die Schmelze, fügt weiteres Schwefelnatrium zur Lösung des teilweise ausgeschiedenen Farbstoffes zu, filtriert heiss und gewinnt den Farbstoff aus dem Filtrat in üblicher Weise, zum Beispiel durch Ausblasen mit Luft oder Ausfällen mit verdünnten Säuren.
Der Farbstoff löst sich in verdünnter Schzvefelnatriumlösung mit olivgrüner Farbe und färbt Baumwolle aus solcher Lösung oder in der Hydrosulfitküpe rotbraun; die Färbungen sind wasch-, licht- und chlorecht.
In der ersten Phase der Reaktion, das ist bei der Kondensation, kann an Stelle des o . Aminothiophenols die äquivalente Menge o . o . Diaminodiphenyldisulfid oder Anilin- o. thiosulfosäure verwendet werden.
Process for the preparation of a cotton dye. The invention is based on the observation that arylquinones, in particular halogenated benzoquinones, interact with o. Aminoaryl mercaptans condense and the condensation products obtained in this way, when treated with the usual sulphurizing agents, are converted into higher sulphurised bodies.
which cotton in the sulfur sodium bath or in the hydrosulphite vat really stains. The o. Aminoaryl mercaptan can be used as such or in the form of an equivalent compound which, in the course of the reaction, generates an o. Aminoaryl mercaptan, for example in the form of an o. o. Dinitro or o. o. Diaminodiaryl disulfide, an o. Aminoarylthiosulfonic acid, a product of the action of chlorosulfur on an aromatic amino body (see Swiss patent no.
71331 and additives) or one of the compounds that result from these action products through the action of water and iXlkalien (see Swiss patent no. 72277 and additives).
The subject of the present patent is a method for the preparation of such a sulfur-containing cotton dye. The process is based on the fact that a halogenated benzoquinone is condensed with o. Amino thiophenol and the condensation product thus formed is further sulphurised with the usual sulphurizing agents. Such a starting material can also be used from which o. Aminothiophenol is formed as an intermediate. The new dye dyes cotton bathing in sodium sulphide or red-brown directly from the vat.
The dyeings are distinguished by good fastness properties, in particular by a remarkable fastness to chlorine.
<I> Example: </I> 25 kg of chloranil (or the equivalent amount of di- or trichloroquinone) and 12.5 kg or similar. Aminothiophenol (or the equivalent amount of o. Aminothiophenol chlorohydrate, or o. Aminothiophenol zinc mercaptide) are mixed with about twenty times the amount of water, alcohol or glacial acetic acid and cooked in a suitable vessel for several hours with thorough stirring. It is advantageous to add an amount of sodium acetate corresponding to the amount of hydrochloric acid released.
After the reaction has ended, the product of the condensation has almost been eliminated in the form of a violet-blue, crystalline powder; the same is filtered off.
20 kg of the condensation product obtained in this way are introduced into a PolSsulfidlösung which is produced by heating 40 kg of crystalline sodium sulfur and 25 kg of sulfur in about 100 liters of water. The whole thing is boiled for a long time, about 60 hours, under reflux, then the melt is diluted, more sodium sulphide is added to the solution of the partially precipitated dye, filtered hot and the dye is recovered from the filtrate in the usual way, for example by blowing out with air or Precipitation with dilute acids.
The dye dissolves in a dilute solution of Schzvefelnodium solution with an olive green color and dyes cotton from such a solution or in the hydrosulfite vat red-brown; the colors are wash, light and chlorinefast.
In the first phase of the reaction, that is during the condensation, instead of the o. Aminothiophenols the equivalent amount o. o. Diaminodiphenyl disulfide or aniline or thiosulfonic acid can be used.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH100190T | 1922-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH100190A true CH100190A (en) | 1923-11-01 |
Family
ID=4358463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100190D CH100190A (en) | 1922-10-03 | 1922-10-03 | Process for the preparation of a sulfur-containing cotton dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH100190A (en) |
-
1922
- 1922-10-03 CH CH100190D patent/CH100190A/en unknown
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