CH254809A - Process for the production of a lively acidic milled dye of the anthraquinone series. - Google Patents
Process for the production of a lively acidic milled dye of the anthraquinone series.Info
- Publication number
- CH254809A CH254809A CH254809DA CH254809A CH 254809 A CH254809 A CH 254809A CH 254809D A CH254809D A CH 254809DA CH 254809 A CH254809 A CH 254809A
- Authority
- CH
- Switzerland
- Prior art keywords
- blue
- dye
- production
- anthraquinone
- acidic
- Prior art date
Links
- 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 6
- 150000004056 anthraquinones Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 230000002378 acidificating effect Effects 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- 239000000975 dye Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- 238000009963 fulling Methods 0.000 claims description 2
- 229920002866 paraformaldehyde Polymers 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- -1 iodine, iron salts Chemical class 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines lebhaften sauren Walkfarbstoffes der Anthrachinonreihe. Es ist aus dem Schweizerischen Patent Nr. 242,846 bekannt, da.ss, wenn man Anthra- cbinonfa.rbstoffe der allgemeinen Formel
EMI0001.0009
worin x und y Alkylreste bedeuten und wo bei der Arylaminorest noch weiter substi tuiert sein kann, mit ha.logenierenden Mitteln behandelt,
Farbstoffe von ausgezeichneten Wasch-, Walk- und Lichtechtheiten und sehr gutem Ziehvermögen aus neutralem Bade erhalten werden.
Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung von sau- ren Farbstoffen der Anthrachinonreihe, die sich ebenfalls durch besonders gute Wasch-, Walle- und Lichtechtheiten auszeichnen, da bei aber erst richtig im schwefelsauren Bade < iuf Wolle aufziehen. Sie zeichnen sieh ferner durch grosse Lebhaftigkeit des Farbtones aus.
-Das Verfahren zur Herstellung dieser neuen Farbstoffe ist dadurch gekennzeichnet, da,ss znan auf Anthrachinonabkömmlinge der all gemeinen Formel
EMI0001.0030
-worin x Halogen oder :eine Sulfogruppe, y Alkylreste, wobei der Arylaminorest noch -weiter durch Alkyl oder Halogen substituiert sein kann, und ein z eine Sulfogruppe, die andern z Wasserstoffatome bedeuten, halo- genfierende Mittel, z. B.
Chlor, Brom, :Sul- furylchlorid und -bromid, einwirken lässt. Die Halogenierung. wird vorzugsweise in Schwefelsäure verschiedener Konzentration, Schwefelsäuremonohydrat oder verdünntem Oleum und in An- oder Abwesenheit von Halogenüberträgern, wie Jod, Eisensalzen usw., bei Temperaturen von 0 bis 40 , wobei die Temperatur am Schluss auf 40 bis 80 gesteigert werden kann, durchgeführt.
In den Fällen, wo x in der allgemeinen Formel Chlor oder Brom bedeutet, -wird ausserdem dieses zweiständige Halogenatom noch mittels Alkalisulfit auf übliche Weise durch die Sulfogruppe ersetzt.
Zur Halogenierung geeignete Ausgangs- produkte sind zum Beispiel: 1-Amino-4- (2',6' - dimethyl - anilido) - anthrachinon- 2,5-, 2,6-, 2,7- und 2,8-disulfosäure, 1-Amino-4- (2', 4', 6' - trimethyl-anilido)-anthrachirion-2, 5-, 2,6-, 2,7- und 2,8-disulfosäure, 1-Amino-4- (2',3',6'-trimethyl-anilido)-anthrachinon-2,5-,
2,6-, 2,7- und 2,8-disulfosäure, 1-Amino-4- (2',6' - dimethyl\- 3'(4')- chlor-anilido) -anthra- ehinon-2,5-, 2,6-, 2,7- und 2,8-disulfosäure; an Stelle der Methylgruppen können homo loge Gruppen, z: B. Athyl, treten.
Statt der freien Sulfosäuren können auch ihre Alkali salze als Ausgangsstoffe verwendet werden.
Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines neuen sauren Walkfarhstoffes der Anthrachinonreihe, wel ches dadurch gekennzeichnet ist, dass man auf 1-Amino-4-(2',6'-dimethylanilido)-anthra- chinon-2,6-disulfonsäure Brom einwirken lässt.
Beispiel: 5,8 Teile 1- amino - 4 - (2';6'-dimethylani- lido)-anthrachinon-2,6-disulfosaures Kalium werden bei Raumtemperatur unter Rühren durch Eintragen in 50 Teile Schwefelsäure 90% gelöst. Hierauf lässt man 1,8 Teile Brom zutropfen, rührt über Nacht bei 20 bis 30 ; erhöht gegebenenfalls die Temperatur noch während 3 Stunden auf 60 .
Den bro- mierten Farbstoff arbeitet man in üblicher Weise auf, sei es durch Giessen der Schwe- felsäureiösung in Eis und Wasser oder durch fraktionierte Fällung des sauren schwefel sauren Salzes aus der Schwefelsäurelösung mittels Zusatz von wenig Wasser.
Der Farbstoff wird in rotstickig blauen Nädelchen gewonnen, die sich in Wasser mit leuchtend grünstickig blauer Farbe leicht lösen. Die Farbe der Lösung in konz. Schwe- felsäure ist schmutzig rotstickig blau; beim Zusatz von wenig Paraformaldehyd schlägt sie nach leuchtend rots:tichig blau um.
Der Farbstoff färbt tierische Fasern, wie Wolle. ,Seide usw., sowie künstliche Fasern, z. B. Superpolyamidfasern, in leuchtend blauen Tönen von -ausgezeichneten Echtheitseigen schaften: Er besitzt die Formel
EMI0002.0070
Process for the production of a lively acidic milled dye of the anthraquinone series. It is known from Swiss patent no. 242,846 that when one uses anthracbinon fibers of the general formula
EMI0001.0009
where x and y mean alkyl radicals and where the arylamino radical can be further substituted, treated with ha.logging agents,
Dyes with excellent washing, fulling and light fastness properties and very good drawability can be obtained from neutral baths.
The present invention relates to a process for the production of acidic dyes of the anthraquinone series, which are also distinguished by particularly good wash, swell and light fastness properties, but only really get absorbed on wool in a sulfuric acid bath. They are also characterized by the great vividness of the hue.
-The process for the preparation of these new dyes is characterized in that, ss znan on anthraquinone derivatives of the general formula
EMI0001.0030
where x is halogen or: a sulfo group, y alkyl radicals, where the arylamino radical can still be substituted by alkyl or halogen, and a z is a sulfo group, the other z are hydrogen atoms, halogenating agents, eg. B.
Chlorine, bromine,: sulfuryl chloride and bromide, can act. The halogenation. is preferably carried out in sulfuric acid of various concentrations, sulfuric acid monohydrate or dilute oleum and in the presence or absence of halogen carriers such as iodine, iron salts, etc., at temperatures from 0 to 40, whereby the temperature can be increased to 40 to 80 at the end.
In cases where x in the general formula denotes chlorine or bromine, this two-position halogen atom is also replaced by the sulfo group in the customary manner by means of alkali metal sulfite.
Starting products suitable for halogenation are, for example: 1-amino-4- (2 ', 6' - dimethyl - anilido) - anthraquinone-2,5-, 2,6-, 2,7- and 2,8-disulfonic acid , 1-Amino-4- (2 ', 4', 6 '- trimethyl-anilido) -anthraquinone-2, 5-, 2,6-, 2,7- and 2,8-disulfonic acid, 1-amino-4 - (2 ', 3', 6'-trimethyl-anilido) -anthraquinone-2,5-,
2,6-, 2,7- and 2,8-disulfonic acid, 1-amino-4- (2 ', 6' - dimethyl \ - 3 '(4') - chloro-anilido) -anthra- ehinon-2, 5-, 2,6-, 2,7- and 2,8-disulfonic acids; Homologous groups, e.g. ethyl, can take the place of methyl groups.
Instead of the free sulfonic acids, their alkali salts can also be used as starting materials.
The present patent relates to a process for the production of a new acidic milled fiber of the anthraquinone series, wel Ches is characterized in that 1-amino-4- (2 ', 6'-dimethylanilido) -anthraquinone-2,6-disulfonic acid Lets bromine act.
Example: 5.8 parts of 1-amino-4 - (2 '; 6'-dimethylanilido) -anthraquinone-2,6-disulphonic acid potassium are dissolved in 50 parts of 90% sulfuric acid at room temperature with stirring by adding 50 parts. 1.8 parts of bromine are then added dropwise, and the mixture is stirred overnight at 20 to 30; if necessary, increase the temperature to 60 for a further 3 hours.
The brominated dye is worked up in the usual way, be it by pouring the sulfuric acid solution into ice and water or by fractional precipitation of the acid sulfuric acid salt from the sulfuric acid solution by adding a little water.
The dye is obtained in red needle-like blue needles, which easily dissolve in water with a bright green blue color. The color of the solution in conc. Sulfuric acid is dirty, red and blue; with the addition of a little paraformaldehyde, it turns bright red: tinged blue.
The dye dyes animal fibers such as wool. , Silk, etc., as well as artificial fibers, e.g. B. Superpolyamide fibers, in bright blue tones of excellent authenticity properties: It has the formula
EMI0002.0070
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH254809T | 1946-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH254809A true CH254809A (en) | 1948-05-31 |
Family
ID=4470767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH254809D CH254809A (en) | 1946-07-26 | 1946-07-26 | Process for the production of a lively acidic milled dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH254809A (en) |
-
1946
- 1946-07-26 CH CH254809D patent/CH254809A/en unknown
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