CH197285A - 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
- CH197285A CH197285A CH197285DA CH197285A CH 197285 A CH197285 A CH 197285A CH 197285D A CH197285D A CH 197285DA CH 197285 A CH197285 A CH 197285A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- blue
- anthraquinone series
- preparation
- mol
- 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 5
- 150000004056 anthraquinones Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 238000009963 fulling Methods 0.000 claims 1
- 238000003780 insertion Methods 0.000 claims 1
- 230000037431 insertion Effects 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 230000007096 poisonous effect Effects 0.000 claims 1
- 239000000975 dye Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 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 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Farbstoffes der Anthrachinonr eihe. Es wurde gefunden, dass wertvolle Farb stoffe der Anthrachinonreihe erhalten wer den, wenn man 1-Amino-4-halogenanthra- chinon-2-sulfosä@uren mit Diaminodiphenyl- methan- bezw. Diaminotriphenylmethanderi- vaten umsetzt.
Unter Diaminodiphenylme- tb.anderivaten sollen auch solche verstanden sein, bei denen das Brückenkohlenstoffatom Glied eines gohlenstoffringes, wie zum Bei spiel eines Cycloheganringes ist.
Die Um setzung wird in wässrig alkoholischem Me dium unter Zusatz eines säurebindenden Mit tels, wie Soda oder Bicarbonat, sowie even tuell eines Katalysators, wie zum Beispiel eines Cupri- oder Cuprosalzes bei erhöhter Temperatur durchgeführt, wobei 2 Mol der 1-Amino-4-halogenanthrachinon-2-sulfosäure mit einem Mol der Diaminoverbindung reagieren. Die erhältlichen Farbstoffe lösen sich in Wasser mit blauer bis blaugrüner Farbe und färben Wolle aus saurem Bade in blauen bis blaugrünen Tönen an.
Die Fär- bungen zeichnen sich durch besonders gute Wasch-, Walk- und Lichtechtheit aus.
Gegenstand vorliegenden Patentes ist nmi ein Verfahren zur Herstellung eines Farb stoffes der Anthrachinonreihe und besteht darin, dass! man auf 2 Mol 1-Amino-4- halogenanthrachinon-2-sulfosäure in wässrig alkoholischem Medium 1 Mol 4 . 4'-Diamino- diphenyl -1 .<B>l'-</B> cyclohegan einwirken lässt. Das Umsetzungsprodukt stellt blaue Nadeln dar, die sich in Wasser mit blaustichig grüner Farbe lösen.
Wolle wird aus schwach saurem oder neutralem Bade in blauen Tönen angefärbt. Die Färbungen zeigen eine gute Walk- und Sä'urekochechtheit. <I>Beispiel:</I> 20 Gewichtsteile 1-Amino-4-bromanthra- chinon-2-sulfosäure werden in 300 Gewichts teilen Wasser und 100 Gewichtsteilen Me thylalkohol unter Zusatz von 20 Gewichts teilen 4.4'Diaminodiphenyl-1.1'-cyclohegan, 2Ö Gewichtsteilen Soda., und 1 Gewichtsteil Kupfersulfat so lange zum Sieden erhitzt,
bis die anfangs gelbrote Lösung intensiv grün- stichi@--blau geworden ist. Schon -während der Reaktion scheidet sich der gebildete Farb stoff in blauen Nadeln ab. welche auf üb liche -Weise isoliert werden.
Process for the preparation of a dye of the anthraquinone series. It has been found that valuable dyes of the anthraquinone series are obtained when 1-amino-4-halogenanthraquinone-2-sulfonic acids with diaminodiphenyl methane or. Diaminotriphenylmethanderi- converts.
Diaminodiphenylmetb.anderivaten should also be understood to mean those in which the bridging carbon atom is a member of a carbon ring, such as a cyclohegan ring, for example.
The conversion is carried out in an aqueous alcoholic medium with the addition of an acid-binding agent, such as soda or bicarbonate, and possibly a catalyst, such as a cupric or cupro salt, at an elevated temperature, with 2 moles of the 1-amino-4- halogenanthraquinone-2-sulfonic acid react with one mole of the diamino compound. The available dyes dissolve in water with a blue to blue-green color and dye wool from an acid bath in blue to blue-green shades.
The dyeings are distinguished by particularly good wash, milled and lightfastness.
The subject of the present patent is nmi a process for the production of a dye of the anthraquinone series and consists in that! one mole of 4 to 2 moles of 1-amino-4-halogenanthraquinone-2-sulfonic acid in an aqueous alcoholic medium. 4'-Diaminodiphenyl -1. <B> l'- </B> cyclohegan can act. The reaction product is blue needles that dissolve in water with a bluish green color.
Wool is dyed in blue tones from weakly acidic or neutral baths. The dyeings show good fullness and acid boiling fastness. <I> Example: </I> 20 parts by weight of 1-amino-4-bromoanthraquinone-2-sulfonic acid are dissolved in 300 parts by weight of water and 100 parts by weight of methyl alcohol with the addition of 20 parts by weight of 4.4'diaminodiphenyl-1.1'-cyclohegan, 20 parts by weight of soda., And 1 part by weight of copper sulphate heated to the boil for
until the initially yellow-red solution has turned an intense green tinge @ - blue. Already -during the reaction, the dye formed is deposited in blue needles. which are isolated in the usual way.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE197285X | 1935-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH197285A true CH197285A (en) | 1938-04-30 |
Family
ID=5756280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH197285D CH197285A (en) | 1935-09-21 | 1936-09-18 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH197285A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1610322B1 (en) * | 1966-09-12 | 1970-08-27 | Herbert Alberts | Process for the production of a zipper |
-
1936
- 1936-09-18 CH CH197285D patent/CH197285A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1610322B1 (en) * | 1966-09-12 | 1970-08-27 | Herbert Alberts | Process for the production of a zipper |
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