CH172731A - Process for the preparation of a dye of the anthraquinone series. - Google Patents
Process for the preparation of a dye of the anthraquinone series.Info
- Publication number
- CH172731A CH172731A CH172731DA CH172731A CH 172731 A CH172731 A CH 172731A CH 172731D A CH172731D A CH 172731DA CH 172731 A CH172731 A CH 172731A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- anthraquinone
- anthraquinone series
- group
- 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
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 11
- 210000002268 wool Anatomy 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- SULNLNVYOGZGNK-UHFFFAOYSA-N 4-methylsulfinylaniline Chemical compound CS(=O)C1=CC=C(N)C=C1 SULNLNVYOGZGNK-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- 125000003375 sulfoxide group Chemical group 0.000 description 4
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XMHURZUZMXPHPS-UHFFFAOYSA-N 4-[(4-aminophenyl)methylsulfinylmethyl]aniline Chemical compound C1=CC(N)=CC=C1CS(=O)CC1=CC=C(N)C=C1 XMHURZUZMXPHPS-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 hydrocarbon radical Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000101 thioether group Chemical group 0.000 description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Farbstoffes der Anthrachinonreihe. Es wurde gefunden, dass sich neue An thrachinonderivate dadurch erhalten lassen, dass man in Anthrachinon oder :seine Sub- stitutionspradukte ein- oder mehrmals .die Gruppe NH. R. SO. R, und ausserdem Sulfo- gruppen einführt.
In obiger Formel bedeutet R einen unsubstituierten oder substituierten Arylrest, R, einen Kohlenwasserstoffrest, wie Alkyl, Aryl, Aralkyl oder Hydroaryl, welcher ebenfalls substituiert sein kann.
Die neuen Produkte sind wertvolle Woll farbstoffe von guten Echtheitseigenschaften und insbesondere gutem Egalisierungsver- mögen.
Die Einführung der genannten Gruppen kann in der verschiedensten Weise erfolgen. Zum Beispiel kann man zunächst Anthra- chinonsulfosäuren herstellen, welche Reste enthalten, die sich durch Aminreste ersetzen lassen, wie zum Beispiel Halogenatome, Oxy- gruppen etc. Diese substituierten Anthrachinonsulfo- säuren werden .dann entweder mit Körpern der Formel HZN . R .
SO. R,. in für .derartige Aminkondensationen üblicher Weise umge setzt, .oder aber man setzt .die eben genann ten Anthrachinonsulfosäuren mit" Körpern der Formel HY. R. S. R, um und führt die Sulfidgruppe gleichzeitig oder nachträglich durch Oxydation in die Sulfoxydgruppe über.
Eine andere Darstellungsweise der neuen Produkte ist die, dass man in Anthrachinon oder seine Substitutionsprodukte zunächst die Gruppe -NH-R-S-R, einführt, die Reaktions produkte sulfiert und gleichzeitig oder nach träglich zu den Sulfoxyden oxydiert. Weiter hin kann man zum Beispiel die Einführung der Sulfogruppe derart .durchführen, dass man im Molekül befindliches Halogen mittelst neutraler .Sulfite durch die Sulfogruppe er setzt.
Dieses Verfahren ist insbesondere für die Herstellung von Körpern der Formel
EMI0002.0001
von Wert, wobei es gleichgültig ist, ob die Suföxydgruppe vor oder nach .der Einfüh rung der Sulfogxuppen gebildet wird.
Man kann zum Beispiel folgende Reaktionen durchführen:
EMI0002.0006
EMI0002.0007
Die Oxydation der Sulfidgruppe zu der Sulf- oxydgruppe kann bei Körpern die noch keine Sulfogruppen enthalten, zum Beispiel mit- telst H=O, oder Bleitetraaoetat in Gegenwart eines organischen Lösungsmittels wie Eis essig,durchgeführt werden.
Bei sulfogruppen- haltigen Körpern verwendet man zweck mässig Wasser als Lösungsmittel oder An- schlämmittel und Wasserstoffsuperoxyd als Oxydationsmittel. Die neuen Produkte sind in Wasser sehr leicht löslich und lassen sich aus .diesen Lösungen durch Aussalzen isolie ren. Sie sind durchweg wertvolle Wollfarb- stoffe, die Wolle aus saurem Bade je nach ihrer Konstitution in den verschiedensten Nuancen anfärben.
Sie zeichnen sich vor analog gebauten Anthrachinon-Amin-Kon- densationsprodukten insbesondere durch leichtere Löslichkeit und besseres Egalisie- rungsvermögen aus.
Gegenstand vorliegenden Patentes ist nun ein Verfahren zur Herstellung eines Anthra- chinonderivates durch Umsetzung von 1- Ainino-4-bromanthraehinon-2-sulfosäure mit 4-Aminophenyl-methylsulfoxyd. Die Reak tion wird in alkalischer Lösung und zweck- mä.ssig in Gegenwart eines Cuprosalzes als Katalysator durchgeführt. Der neue Farb stoff färbt Wolle aua saurem Bade in blauen Tönen von guter Egalität an.
<I>Beispiel:</I> 10 Gewichtsteile 1-Amino-4-bromanthra- ehinon-2-sulfosäure, 10 Gewichtsteile 4-Ami- nophenyl-methylsulfoxyd, 12 Gewichtsteile Natriumbikarbonat, 0,5 Gewichtsteile Kup- ferchlorür, werden in 150 Gewichtsteilen Wasser eingetragen und bei 70 bis<B>100'</B> so. lange auf Temperatur gehalten, bis eine klare blaue Lösung entstanden ist. Aus dieser wird der gebildete Farbstoff, der folgende Konstitution besitzt
EMI0002.0046
durch Zusatz von $aliumchlorid kristallin abgeschieden.
Er färbt Wolle äus saurem Bade in blauen Tönen an; die Färbung zeich net sich durch gute Egalität aus.
Process for the preparation of a dye of the anthraquinone series. It has been found that new anthraquinone derivatives can be obtained by one or more times .the group NH in anthraquinone or: its substitution products. R. SO. R, and also introduces sulfo groups.
In the above formula, R denotes an unsubstituted or substituted aryl radical, R denotes a hydrocarbon radical, such as alkyl, aryl, aralkyl or hydroaryl, which can likewise be substituted.
The new products are valuable wool dyes with good fastness properties and, in particular, good leveling properties.
The groups mentioned can be introduced in the most varied of ways. For example, one can first prepare anthraquinone sulfonic acids which contain radicals that can be replaced by amine radicals, such as halogen atoms, oxy groups, etc. These substituted anthraquinone sulfonic acids are then either with bodies of the formula HZN. R.
SO. R ,. in the usual manner for such amine condensations, or else the above-mentioned anthraquinone sulfonic acids are converted with "bodies of the formula HY. R. S. R" and the sulfide group is converted into the sulfoxide group simultaneously or subsequently by oxidation.
Another way of presenting the new products is to first introduce the -NH-R-S-R group in anthraquinone or its substitution products, sulfate the reaction products and oxidize them to the sulfoxides at the same time or afterwards. Furthermore, for example, the sulfo group can be introduced in such a way that halogen in the molecule is replaced by the sulfo group by means of neutral sulfites.
This process is particularly useful for making bodies of the formula
EMI0002.0001
of value, regardless of whether the sulfoxide group is formed before or after the introduction of the sulfoxide groups.
For example, the following reactions can be carried out:
EMI0002.0006
EMI0002.0007
The oxidation of the sulfide group to the sulfoxide group can be carried out in the presence of an organic solvent such as glacial acetic acid in bodies which do not yet contain any sulfo groups, for example by means of H = O or lead tetraacetate.
In the case of bodies containing sulfo groups, it is expedient to use water as the solvent or slurry and hydrogen peroxide as the oxidizing agent. The new products are very easily soluble in water and can be isolated from these solutions by salting out. They are all valuable wool dyes that dye wool from an acid bath in various shades, depending on its constitution.
They are distinguished from analogously constructed anthraquinone-amine condensation products in particular by easier solubility and better leveling power.
The present patent now relates to a process for the preparation of an anthrachinone derivative by reacting 1-amino-4-bromoanthraehinone-2-sulfonic acid with 4-aminophenyl-methyl sulfoxide. The reaction is carried out in an alkaline solution and expediently in the presence of a cupro salt as a catalyst. The new dye dyes wool from an acidic bath in blue tones with good levelness.
<I> Example: </I> 10 parts by weight of 1-amino-4-bromoanthraquinone-2-sulfonic acid, 10 parts by weight of 4-aminophenyl-methylsulfoxide, 12 parts by weight of sodium bicarbonate, 0.5 part by weight of copper chloride are added to 150 Parts by weight of water entered and at 70 to <B> 100 '</B> so. kept at temperature for a long time until a clear blue solution has formed. This becomes the dye formed, which has the following constitution
EMI0002.0046
deposited in crystalline form by the addition of aluminum chloride.
He dyes wool from an acid bath in shades of blue; the coloring is characterized by good levelness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE172731X | 1932-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH172731A true CH172731A (en) | 1934-10-31 |
Family
ID=5690207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH172731D CH172731A (en) | 1932-10-21 | 1933-10-12 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH172731A (en) |
-
1933
- 1933-10-12 CH CH172731D patent/CH172731A/en unknown
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