AT30641B - Process for the preparation of o-oxyazo dyes from 1,5-aminonaphtol. - Google Patents
Process for the preparation of o-oxyazo dyes from 1,5-aminonaphtol.Info
- Publication number
- AT30641B AT30641B AT30641DA AT30641B AT 30641 B AT30641 B AT 30641B AT 30641D A AT30641D A AT 30641DA AT 30641 B AT30641 B AT 30641B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- aminonaphtol
- preparation
- dyes
- oxyazo
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N ortho-hydroxyaniline Natural products NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 4
- 238000004040 coloring Methods 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- -1 o-aminophenol sulfonic acids Chemical class 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XJPRTTVYHDTSAT-UHFFFAOYSA-N 3-amino-4-hydroxy-2-methylbenzenesulfonic acid Chemical compound OC1=C(C(=C(C=C1)S(=O)(=O)O)C)N XJPRTTVYHDTSAT-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- JIXWSQQKJPQJGV-UHFFFAOYSA-N CC(C1)(C(O)=CC=C1S(O)(=O)=O)N Chemical compound CC(C1)(C(O)=CC=C1S(O)(=O)=O)N JIXWSQQKJPQJGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Investigating Or Analysing Biological Materials (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von o-Oxyazofarbstoffen aus 1. 5-Amlnonaphtol.
In der Stamm-Patentschrift Nr. 28707 sind o-Oxymonoazofarbstoffe beschrieben, die durch Vereinigung von diazotierten o-Aminophenolsulfosäuron und deren Derivaten mit l. H-Aminonaphtol in alk alischer Lösung erhalten werden.
Diese Farbstoffe zeichnen sich besonders durch hohe Pottingechtheit aus.
Es wurde nun weiter gefunden, dass diejenigen o-Oxymonoazofarbstoffe, die sich von denselben Komponenten, also einerseits von o-Aminophenolsulfosäuren und deren Derivaten und andererseits von 1. 5-Aminonaphtol ableiten, bei denen aber die Kupplung in saurer Lösung vorgenommen worden ist, analoge Echtheitseigenschafton besitzen.
Zur Darstellung dieser Farbstoffe verfährt man z. 11. folgendermassen : 1H kg o-Aminophenolsulfosäure werden in üblicher Weise diazotiert und zu einer wässerigen Lösung von 20 ]0 1. 5-AminonaphtolchIorhydrat unter Rühren zugegeben. Die vorhandene freie Mineralsäure wird durch Zugabe von essigsaurem Natron so weit abgestumpft, dass Kongopapier nicht mehr gebläut wird. Nach längerem Rühren ist die Farbstoffbildung nahezu beendet und wird durch gelindes Erwärmen vollständig zu Ende geführt. Es wird mit Sodalösung schwach alkalisch gemacht, der Farbstoff ausgesalzen, gepresst und getrocknet.
Er färbt Wolle in saurem Bade rotviolett an, beim Nacbchromieren wird ein sattes Schwarz erhalten.
EMI1.1
der o-Aminophonolsulfosäuro und 1. 5-Aminonaphto1.
In folgender Tabelle sind die Eigenschaften einer Anzahl typischer Vertreter dieser
EMI1.2
EMI1.3
<tb>
<tb> Farbstoff <SEP> aus <SEP> Direkte <SEP> Färbung <SEP> Nachchromierte <SEP> Färbung
<tb> o-Aminophenol-p-sulfosäure
<tb> (Beilstein <SEP> II, <SEP> 8. <SEP> 838) <SEP> retvielett <SEP> schwarz
<tb> + <SEP> 1.5-Aminonaphtel
<tb> o-Aminophenol-p-chlor-o-sulfosäure
<tb> (Französische <SEP> Patentschrift <SEP> Nr. <SEP> 301530) <SEP> violett <SEP> schwarz
<tb> + <SEP> 1.5-Aminonaphtol
<tb> o-Amino-o-kresol-p-sulfosäure
<tb> (Deutsche <SEP> Patentschrift <SEP> Nr. <SEP> 45994) <SEP> rotviolett <SEP> schwarz
<tb> + <SEP> 1.5-Aminonaphtol
<tb> o-Amino-m-kresol-p-sulfosäure
<tb> (analog <SEP> wie <SEP> Nr. <SEP> 3 <SEP> hergestellt) <SEP> rotviolett <SEP> schwarz
<tb> + <SEP> 1.5-Aminonaphtol
<tb>
<Desc / Clms Page number 1>
Process for the preparation of o-oxyazo dyes from 1. 5-aminonaphtol.
In the parent patent specification No. 28707 o-Oxymonoazo dyes are described, which by combining diazotized o-aminophenol sulfonic acid and its derivatives with l. H-aminonaphtol can be obtained in alkaline solution.
These dyes are particularly notable for their high potting resistance.
It has now also been found that those o-oxymonoazo dyes which are derived from the same components, i.e. on the one hand from o-aminophenol sulfonic acids and their derivatives and on the other hand from 1,5-aminonaphthol, but in which the coupling has been carried out in acidic solution, are analogous Have authenticity properties.
To represent these dyes one proceeds z. 11. As follows: 1H kg of o-aminophenolsulphonic acid are diazotized in the usual way and added to an aqueous solution of 20] 0.15-aminonaphthol chloride with stirring. The free mineral acid that is present is blunted by adding sodium acetate to such an extent that Congo paper is no longer blued. After prolonged stirring, the dye formation is almost complete and is brought to an end by gentle warming. It is made weakly alkaline with a soda solution, the dye is salted out, pressed and dried.
It stains wool in an acidic bath red-violet; when it is chromed, a deep black is obtained.
EMI1.1
der o-aminophonolsulfosäuro and 1. 5-aminonaphto1.
The following table shows the properties of a number of typical representatives of these
EMI1.2
EMI1.3
<tb>
<tb> Dye <SEP> from <SEP> Direct <SEP> coloring <SEP> Chromed <SEP> coloring
<tb> o-aminophenol-p-sulfonic acid
<tb> (Beilstein <SEP> II, <SEP> 8. <SEP> 838) <SEP> retvielett <SEP> black
<tb> + <SEP> 1.5-aminonaphtel
<tb> o-aminophenol-p-chloro-o-sulfonic acid
<tb> (French <SEP> patent specification <SEP> No. <SEP> 301530) <SEP> violet <SEP> black
<tb> + <SEP> 1,5-aminonaphtol
<tb> o-amino-o-cresol-p-sulfonic acid
<tb> (German <SEP> patent specification <SEP> no. <SEP> 45994) <SEP> red-violet <SEP> black
<tb> + <SEP> 1,5-aminonaphtol
<tb> o-amino-m-cresol-p-sulfonic acid
<tb> (similar to <SEP> like <SEP> No. <SEP> 3 <SEP> manufactured) <SEP> red-violet <SEP> black
<tb> + <SEP> 1,5-aminonaphtol
<tb>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1903180481D DE180481C (en) | 1903-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT30641B true AT30641B (en) | 1907-11-11 |
Family
ID=5711327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT30641D AT30641B (en) | 1903-02-16 | 1906-10-27 | Process for the preparation of o-oxyazo dyes from 1,5-aminonaphtol. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT30641B (en) |
-
1906
- 1906-10-27 AT AT30641D patent/AT30641B/en active
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