CH188519A - Process for the preparation of a new monoazo dye. - Google Patents
Process for the preparation of a new monoazo dye.Info
- Publication number
- CH188519A CH188519A CH188519DA CH188519A CH 188519 A CH188519 A CH 188519A CH 188519D A CH188519D A CH 188519DA CH 188519 A CH188519 A CH 188519A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- pure
- dye
- bluish
- preparation
- Prior art date
Links
- 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 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- 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 claims description 3
- LHEPTIRLRDQRQR-UHFFFAOYSA-N 2,4-bis(2-methylphenoxy)aniline Chemical compound CC1=CC=CC=C1OC1=CC=C(N)C(OC=2C(=CC=CC=2)C)=C1 LHEPTIRLRDQRQR-UHFFFAOYSA-N 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000013535 sea water Substances 0.000 claims description 3
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines neuen mlonoazofarbstoffes. Es wurde gefunden, dass man einen neuen, wertvollen Monoazofarbstoff erhält, wenn man die Diazoverbindung von 4-Arnino-resorcin- di-o-tolyläther von der Formel
EMI0001.0006
mit 8-p-Toluolsulfoylamino-l-oxy-naphthalin- disulfonsäure-(3.6) kuppelt.
Der neue Farbstoff bildet ein bläulich rotes Pulver, welches in Wasser mit lebhaft blaustichig roter, in konzentrierter Schwefel säure mit reinblauer Farbe löslich ist. Er färbt Wolle, Seide und Zelluloseesterlacke in sehr schönen, reinen rotvioletten Tönen von sehr guter Lichtechtheit;
die Textil färbungen zeigen ausserdem noch eine gute Walkbeständigkeit und eine besonders gute Seewasserechtheit. Der reine und blaustichige Farbton des neuen Farbstoffes ist in seiner Lebhaftigkeit in der Azoreihe unübertroffen. <I>Beispiel:</I> 30,5 kg 4-Amino-resorcin-di-o-tolyläther, eine farblose, feste Substanz, welche erhalten wird, indem man 2.4-Dichlornitrobenzol mit o-Kresol in Gegenwart von Alkalihydroxyd bei Temperaturen von 130 -150 zur Um setzung bringt, reduziert und im Vakuum destilliert (258-259 bei 15-16 mm) wer den dianotiert.
Die Diazolösung lässt man unter gutem Rühren .bei 0 in eine wässerige Lösung von 47,5 kg 8-p-Toluolsulfoylamino- 1-oxy-naphthalin-disulfonsäure-(3.6) und über schüssigem Natriumacetat einlaufen. Durch allmähliche Zugabe von Sodalösung wird neutralisiert. Nach beendeter Kupplung wird aufgeheizt, ausgesalzen, filtriert und ge trocknet.
Der erhaltene Farbstoff bildet ein bläu lich-rotes Pulver, das in Wasser mit lebhaft blaustichig roter, in konzentrierter Schwefel säure mit reinblauer Farbe löslich ist. Er färbt Wolle und Seide in klaren, rotvioletten Tönen ton sehr guter Licht- und Walkecht- heit und vorzüglicher Seewasserechtheit. Die Lichtechtheit eines mit dem neuen Farbstoff gefärbten Zelluloseesterlackes ist hervor ragend.
Process for the preparation of a new mlonoazo dye. It has been found that a new, valuable monoazo dye is obtained if the diazo compound of 4-amino-resorcinol-di-o-tolyl ether of the formula
EMI0001.0006
with 8-p-toluenesulfoylamino-l-oxy-naphthalene-disulfonic acid- (3.6) couples.
The new dye forms a bluish red powder, which is soluble in water with a vivid bluish red color and in concentrated sulfuric acid with a pure blue color. It dyes wool, silk and cellulose ester lacquers in very beautiful, pure red-violet shades of very good lightfastness;
The textile dyeings also show good flexing resistance and particularly good seawater fastness. The pure and bluish hue of the new dye is unsurpassed in its liveliness in the azo range. <I> Example: </I> 30.5 kg of 4-amino-resorcinol-di-o-tolyl ether, a colorless, solid substance which is obtained by reacting 2,4-dichloronitrobenzene with o-cresol in the presence of alkali metal hydroxide at temperatures from 130-150 to implement, reduced and distilled in vacuo (258-259 at 15-16 mm) who dianotiert.
The diazo solution is allowed to run into an aqueous solution of 47.5 kg of 8-p-toluenesulfoylamino-1-oxynaphthalene-disulfonic acid (3.6) and excess sodium acetate with thorough stirring. Gradual addition of soda solution will neutralize. After the coupling has ended, the mixture is heated, salted out, filtered and dried.
The dye obtained forms a bluish-red powder which is soluble in water with a vivid bluish red, in concentrated sulfuric acid with a pure blue color. It dyes wool and silk in clear, red-violet shades with very good lightfastness and flexing fastness and excellent seawater fastness. The lightfastness of a cellulose ester varnish colored with the new dye is excellent.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH184014T | 1935-09-24 | ||
| CH188519T | 1935-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH188519A true CH188519A (en) | 1936-12-31 |
Family
ID=25720962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH188519D CH188519A (en) | 1935-09-24 | 1935-09-24 | Process for the preparation of a new monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH188519A (en) |
-
1935
- 1935-09-24 CH CH188519D patent/CH188519A/en unknown
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