CH185584A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH185584A CH185584A CH185584DA CH185584A CH 185584 A CH185584 A CH 185584A CH 185584D A CH185584D A CH 185584DA CH 185584 A CH185584 A CH 185584A
- Authority
- CH
- Switzerland
- Prior art keywords
- leather
- preparation
- dyes
- dye
- azo dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000987 azo dye Substances 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 16
- 239000010985 leather Substances 0.000 claims description 9
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- -1 copper complex compound Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims 1
- 238000004043 dyeing Methods 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 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
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 150000002790 naphthalenes Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Azofarbstoffes. Es wurde gefunden, dass, man wertvolle Azofarbstoffe erhält, wenn man Monoazo- farbstoffe der allgemeinen Formel:
EMI0001.0006
worin x für Hydroxyl, Alkoxy, Halogen oder die Carboxylgruppe und y für Hydro- xyl, die Amino- oder eine substituierte Amidogruppe steht, ein z die gleichen Substituenten wie y bedeutet und das andere z für Wasserstoff oder einen beliebigen Substituenten steht,
worin R einen Benzol oder Naphthalinkern bedeutet und R und der Benzolkern R' noch weiterhin beliebig substituiert sein können, mit einer beliebi gen Diazotierungskomponente, ausschliesslich Aminoazokörpern, kombiniert, auf welche Farbstoffe noch eine dritte Diazotierungs- komponente gekuppelt werden kann,
und die so erhältlichen Farbstoffe vor oder nach der letzten Kupplung mit metallabgebenden Mitteln in die Sehwermetallkomplexverbin- dungen der entsprechenden o-Oxy- bezw. o-Carboxyazofarbstoffe nach an sich bekann ten Methoden überführt.
Gegenüber bekannten vergleichbaren Farbstoffen weisen die nach dem vorliegen den Verfahren erhältlichen den technischen Fortschritt auf, dass sie gegen Säure un empfindlicher sind.
Die so erhältlichen Farbstoffe eignen sich besonders zum Färben von Leder; sie liefern egale Färbungen, die eine sehr gute Lichtechtheit aufweisen.
Die Farbstoffe können sich in gleicher Weise für chrom- und vegetabilisch ge gerbte Leder, die Chromkomplexf arbstof f e auch für Glaceleder, eignen.
Ferner können die nach dem Verfahren darstellbaren Farbstoffe zum Färben von tierischen und pflanzlichen Fasern verwen det werden.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines neuen: Azofarbstoffes. Es ist dadurch ge kennzeichnet, dass man 2 Mol diazotierte 2:
-Anisidin-4-sulfonsäure mit 1 Mol Resorcin kuppelt und den erhaltenen Disazofarbstoff durch Behandlung mit einem Kupfer abge benden Mittel in die Kupferkomplexverbiu- dung überführt.
<I>Beispiel:</I> Der aus 40a6 Gewichtsteilen 2@A.nisidin- 4-sulfonsäure und 11 Gewichtsteilen Resorcin dargestellte Farbstoff wird zur Überführung in den doppelten Kupferlack mit einer Kupferammoniaklösung aus 49,8 Gewichts teilen Kupfersulfat einige Stunden auf<B>70'</B> erhitzt.
Der auf üblichem Wege isolierte Farbstoff färbt Chromleder, vegetabilisch gegerbtes Leder, sowie Glaceleder, Wolle und Seide in braunroten Tönen.
Process for the preparation of an azo dye. It has been found that valuable azo dyes are obtained if monoazo dyes of the general formula:
EMI0001.0006
where x is hydroxyl, alkoxy, halogen or the carboxyl group and y is hydroxyl, the amino or a substituted amido group, one z is the same substituent as y and the other z is hydrogen or any substituent,
where R is a benzene or naphthalene nucleus and R and the benzene nucleus R 'can still be substituted as desired, combined with any diazotization component, exclusively aminoazo bodies, to which dyes a third diazotization component can be coupled,
and the dyes obtainable in this way before or after the last coupling with metal donating agents in the Sehwermetallkomplexverbin- the corresponding o-oxy- respectively. Transferred o-carboxyazo dyes by methods known per se.
Compared to known, comparable dyes, those obtainable by the present process have the technical progress that they are insensitive to acid.
The dyes obtainable in this way are particularly suitable for dyeing leather; they provide level dyeings that have very good lightfastness.
The dyes can be used in the same way for chrome and vegetable tanned leather, and the chrome complex dyes can also be used for glass leather.
Furthermore, the dyes which can be produced by the method can be used for dyeing animal and vegetable fibers.
The subject of the present patent is a process for the preparation of a new: azo dye. It is characterized in that 2 moles of diazotized 2:
-Anisidine-4-sulfonic acid is coupled with 1 mol of resorcinol and the disazo dye obtained is converted into the copper complex compound by treatment with a copper-releasing agent.
<I> Example: </I> The dye made from 40a6 parts by weight of 2@A.nisidine- 4-sulfonic acid and 11 parts by weight of resorcinol is converted into double copper lacquer with a copper ammonia solution of 49.8 parts by weight of copper sulfate for a few hours > 70 '</B> heated.
The dye, isolated in the usual way, dyes chrome leather, vegetable-tanned leather, as well as glazed leather, wool and silk in brown-red tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE185584X | 1933-11-25 | ||
| CH182397T | 1934-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185584A true CH185584A (en) | 1936-07-31 |
Family
ID=25720705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185584D CH185584A (en) | 1933-11-25 | 1934-11-15 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185584A (en) |
-
1934
- 1934-11-15 CH CH185584D patent/CH185584A/en unknown
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