CH261053A - Process for the preparation of a polyazo dye. - Google Patents
Process for the preparation of a polyazo dye.Info
- Publication number
- CH261053A CH261053A CH261053DA CH261053A CH 261053 A CH261053 A CH 261053A CH 261053D A CH261053D A CH 261053DA CH 261053 A CH261053 A CH 261053A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- black
- parts
- preparation
- moles
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- -1 polyazo Polymers 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
- C09B35/52—Tetrazo dyes of the type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Polyazofarbstoffes. Es wurde gefunden, dass ein Polyazofarb- stoff hergestellt werden kann, wenn man 2 Mol 2,6-Dioxynaphtlialin einerseits mit 1 Mol tetrazotiertem 3,3'-Dioxy-4,4'-diamino- diphenyl und anderseits mit 2 Mol dianotier ter 4-Chlor-2-amino-l-oxybenzol-6-sulfonsäure kuppelt.
Der neue Farbstoff stellt ein grauschwar zes Pulver dar, das sich in Wasser und in 10%iger Natronlauge mit violettschwarzer, in 10%iger Natrium.carbonatlösung mit grün schwarzer und in konzentrierter Schwefel säure mit blauer Farbe löst. Er erzeugt auf Baumwolle nach dein ein- oder zweibadigen Nachkupferungsverfahren graue Töne von hervorragenden Echtheitseigenschaften.
3,3'-1)ioxy-4,4'-diaininodiphenyl kann bei spielsweise durch Verseifen von Dianisidin mit Aluininiiimchlorid erhalten werden und wird in üblicher Weise tetrazotiert.
Die Kupplung des 2,6-Dioxynaphthalins mit dein tetrazotierten 3,3'-Dioxy-4,4'-diamino- diphenyl wird vorzugsweise zuerst durchge führt und kann vorteilhaft in ätzalkalischer Lösung, z. B. in relativ konzentrierter Ka- liumhydroxydlösung vorgenommen werden.
Die Kupplung des so erhaltenen Disazofarb- stoffes mit 2 Mol dianotierter 4-Chlor-2-amino- 1-phenol-6-sulfonsäure wird in alkalischem, beispielsweise phenolphthaleinalkalischem Me dium, durchgeführt.
<I>Beispiel:</I> 21.,6 Teile 3,3'-Dioxy-4,4'-diaminodiphenyl in Form des Dichlorhydrates werden in 100 Teilen Wasser und 12 Volinnteilen konzen trierter Salzsäure suspendiert und bei 5 bis 8 mit einer wässerigen, 13,8 Teile Natriumnitrit enthaltenden Lösung tetrazotiert. Nach been deter Reaktion neutralisiert man durch Bei gabe von 6,4 Teilen wasserfreiem Natriumcar- bonat und filtriert die ausgefallene Tetrazo- verbindung ab.
33,6 Teile 2,6-Dioxynaphthalin werden in 80 Raumteilen Kalilauge von 45 Volumenpro zent gelöst. Man kühlt auf<B>30</B> ab und trägt die Tetrazoverbindung ein. Man kuppelt wäh rend 4 Stunden bei 4 bis 60, während 16 Stun den bei 6 bis<B>100</B> und bis zur Beendigung der Kupplung bei 10 bis 15a. Hierauf verdünnt man die Kupplungsmasse mit 500 Teilen Wasser, setzt 30 Teile Natriumchlorid hinzu, scheidet den Farbstoff durch Zutropfen von 170 Raumteilen 5 % iger Salzsäure ab und fil triert.
Die Disazofarbstoffpaste wird in 1000 Tei len Wasser und 20 Raumteilen Natronlauge von 40 Volumenprozent bei<B>300</B> gelöst. Man kühlt auf<B>30</B> ab und setzt eine auf übliche Weise hergestellte und neutralisierte Diazo- verbindung aus 44,7 Teilen 4-Chlor-2-amino-l- oxybenzol-6-sulfonsäure hinzu. Man kuppelt während 4 Stunden bei 4 bis<B>80</B> und bis zur Beendigung der Reaktion bei 8 bis<B>150.</B> Der neue Tetrakisazofarbstoff ist vollständig aus gefallen.
Man filtriert ab und reinigt den Farbstoff durch Lösen in verdünnter Soda lösung und Aussalzen.
Process for the preparation of a polyazo dye. It has been found that a polyazo dye can be prepared if 2 moles of 2,6-dioxynaphthlialin are dianotized with 1 mole of tetrazotized 3,3'-dioxy-4,4'-diamino-diphenyl on the one hand and 2 moles of dianotized 4 on the other -Chlor-2-amino-1-oxybenzene-6-sulfonic acid couples.
The new dye is a gray-black powder that dissolves in water and in 10% sodium hydroxide solution with violet-black, in 10% sodium carbonate solution with green-black and in concentrated sulfuric acid with blue. It produces gray tones with excellent fastness properties on cotton using your one- or two-bath re-coppering process.
3,3'-1) ioxy-4,4'-diaininodiphenyl can be obtained, for example, by saponifying dianisidine with aluminum chloride and is tetrazotized in the usual way.
The coupling of the 2,6-dioxynaphthalene with your tetrazotized 3,3'-dioxy-4,4'-diamino-diphenyl is preferably carried out first and can advantageously be carried out in a caustic solution, eg. B. be made in relatively concentrated potassium hydroxide solution.
The coupling of the disazo dye thus obtained with 2 mol of dianotized 4-chloro-2-amino-1-phenol-6-sulfonic acid is carried out in an alkaline medium, for example phenolphthalein-alkaline.
<I> Example: </I> 21. 6 parts of 3,3'-dioxy-4,4'-diaminodiphenyl in the form of dichlorohydrate are suspended in 100 parts of water and 12 parts by volume of concentrated hydrochloric acid and at 5 to 8 with a aqueous solution containing 13.8 parts of sodium nitrite tetrazotized. After the reaction has ended, the mixture is neutralized by adding 6.4 parts of anhydrous sodium carbonate and the precipitated tetrazo compound is filtered off.
33.6 parts of 2,6-dioxynaphthalene are dissolved in 80 parts by volume of 45 percent by volume of potassium hydroxide solution. It is cooled to <B> 30 </B> and the tetrazo compound is introduced. The coupling is carried out for 4 hours at 4 to 60, for 16 hours at 6 to 100 and until the coupling is complete at 10 to 15a. The coupling compound is then diluted with 500 parts of water, 30 parts of sodium chloride are added, the dye is separated off by the dropwise addition of 170 parts by volume of 5% hydrochloric acid and filtered.
The disazo dye paste is dissolved in 1000 parts of water and 20 parts by volume of 40 percent by volume sodium hydroxide solution at <B> 300 </B>. The mixture is cooled to <B> 30 </B> and a diazo compound prepared and neutralized in a customary manner from 44.7 parts of 4-chloro-2-amino-l-oxybenzene-6-sulfonic acid is added. Coupling is carried out for 4 hours at 4 to 80 and until the reaction has ended at 8 to 150. The new tetrakisazo dye has completely precipitated.
It is filtered off and the dye is purified by dissolving it in dilute soda solution and salting out.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH257110T | 1942-02-05 | ||
| CH261053T | 1942-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261053A true CH261053A (en) | 1949-04-15 |
Family
ID=25730019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261053D CH261053A (en) | 1942-02-05 | 1942-02-05 | Process for the preparation of a polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261053A (en) |
-
1942
- 1942-02-05 CH CH261053D patent/CH261053A/en unknown
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