AT55220B - Process for the preparation of trisazo dyes. - Google Patents
Process for the preparation of trisazo dyes.Info
- Publication number
- AT55220B AT55220B AT55220DA AT55220B AT 55220 B AT55220 B AT 55220B AT 55220D A AT55220D A AT 55220DA AT 55220 B AT55220 B AT 55220B
- Authority
- AT
- Austria
- Prior art keywords
- sulfonic acid
- preparation
- aminonaphthol
- dyes
- trisazo dyes
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Landscapes
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Trisazofarbstoffen.
Wenn man die Tetrazoverbindung aus p-Aminobenzolazo-2.8-aminonaphtol-6-sulfosäure oder 2. 5-Aminonaphtol-7-sulfosäure mit je 1 Mol. 1.8-Naphtylendiamin-4-sulfosäure und 1 Mol. eines m-Diamins, Phenols, Aminophenols oder eines ihrer Derivate vereinigt, so werden, wie gefunden wurde, Farbstoffe erhalten, die sich vorzüglich zum Färben von Baumwolle eignen und die wertvolle Eigenschaft besitzen, auf der Faser mit diazotiertem p-Nitranilin gekuppelt, ausserordentlich farbkräftige blauschwarze bis tiefschwarze Töne von guter Echtheit zu liefern.
Diese Eigenschaft der neuen Produkte war nicht vorauszusehen, da die bekannten analogen Farbstoffe, in denen die 1. 8-Naphtylendiamin-4-sulfosäure durch andere Kom-
EMI1.1
behandlung mit diazotiertem p-Nitranilin nur braune bis braunschwarze Töne liefern.
Beispiel.
15 Teile Azetyl-p-phenylendiamin werden mit 7 Teilen Natriumnitrit in salzsaurer Lösung in bekannter Weise diazotiert und in eine sodaalkalische Lösung von 24 Teilen 2. 8-Aminouaphtol-G-sulfosäure einfliessen gelassen. Der Mouoazofarbstoff bildet sich sofort und wird durch Kochen mit Natronlauge in bekannter Weise verseift. Nach dem Ansäuern
EMI1.2
säure. Durch allmähliches Abstumpfen der sauren Mischung wird die Bildung des Zwtf"'hcn- prodtrktes beendigt. Hierauf fügt man eine Lösung von 11 Teilen m-Phenylendiamin der Reaktionsmasse zu, macht sodaalkalisch und rührt noch kurze Zeit. Alsdann wird der
Farbstoff abfiltriert und getrocknet.
Er färbt ungebeizte Baumwolle blauschwarz. Beim Nachbehandeln mit diazotiertem p-Nitranilin auf der Faser wird ein tiefes Schwarz von guter Lichtechtheit und hervorragender Waschechtheit erhalten, das sich vorzüglich ätzen lässt.
Im obigen Beispiel kann man m-Phenylendiamin durch andere Diamine oder ihre Derivate, durch Phenole, wie Resorzin, Aminophenol und ihre Derivate oder Homologe, die 2. 8-Aminonaphtol-6-sulfosäure durch 2.5-Aminenaphtol-7-sulfosäure ersetzen. Auch kann man die Tatrazoverbindung zuerst mit einem der Diamine, Phenole usw. und dann mit der 1. 8-Naphtylendiamin-4-sulfosäure zu Farbstoffen vereinigen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of trisazo dyes.
If the tetrazo compound of p-aminobenzolazo-2.8-aminonaphthol-6-sulfonic acid or 2.5-aminonaphthol-7-sulfonic acid is used with 1 mole of 1,8-naphthylenediamine-4-sulfonic acid and 1 mole of a m-diamine, phenol, aminophenol or one of their derivatives is combined, as has been found, dyes are obtained which are eminently suitable for dyeing cotton and which have the valuable property of being coupled with diazotized p-nitroaniline on the fiber to produce extraordinarily strong blue-black to deep black shades of good fastness deliver.
This property of the new products could not be foreseen, since the known analogous dyes, in which the 1. 8-naphthylenediamine-4-sulfonic acid is replaced by other compo-
EMI1.1
treatment with diazotized p-nitroaniline only delivers brown to brown-black tones.
Example.
15 parts of acetyl-p-phenylenediamine are diazotized in a known manner with 7 parts of sodium nitrite in a hydrochloric acid solution and allowed to flow into an alkaline soda solution of 24 parts of 2, 8-aminouaphthol-G-sulfonic acid. The mouoazo dye forms immediately and is saponified in a known manner by boiling with sodium hydroxide solution. After acidification
EMI1.2
acid. By gradually dulling the acidic mixture, the formation of the intermediate product is terminated. A solution of 11 parts of m-phenylenediamine is then added to the reaction mass, it is made alkaline and stirred for a short time
Dye filtered off and dried.
It dyes unstained cotton blue-black. When the fibers are aftertreated with diazotized p-nitroaniline, a deep black of good lightfastness and excellent washfastness is obtained, which is excellent for etching.
In the above example, m-phenylenediamine can be replaced by other diamines or their derivatives, by phenols such as resorcinol, aminophenol and their derivatives or homologues, and the 2. 8-aminonaphthol-6-sulfonic acid by 2.5-aminenaphthol-7-sulfonic acid. The Tatrazo compound can also be combined first with one of the diamines, phenols, etc. and then with the 1,8-naphthylenediamine-4-sulfonic acid to form dyes.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE55220X | 1910-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT55220B true AT55220B (en) | 1912-09-10 |
Family
ID=5628305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT55220D AT55220B (en) | 1910-06-23 | 1911-05-15 | Process for the preparation of trisazo dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT55220B (en) |
-
1911
- 1911-05-15 AT AT55220D patent/AT55220B/en active
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