CH306273A - Process for the preparation of a substantive azo dye. - Google Patents
Process for the preparation of a substantive azo dye.Info
- Publication number
- CH306273A CH306273A CH306273DA CH306273A CH 306273 A CH306273 A CH 306273A CH 306273D A CH306273D A CH 306273DA CH 306273 A CH306273 A CH 306273A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- preparation
- azo dye
- blue
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
- -1 aminomonoazo Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- JCOOFZSBYJRINH-UHFFFAOYSA-N 5-amino-2-[2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=CC=C1S(O)(=O)=O JCOOFZSBYJRINH-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 150000004699 copper complex Chemical class 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- GHBWBMDGBCKAQU-OWOJBTEDSA-N 5-amino-2-[(e)-2-(4-nitro-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O GHBWBMDGBCKAQU-OWOJBTEDSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 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
- 239000013078 crystal Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum 13auptpatent Nr. 303281. Verfahren zur Herstellung eines direktziehenden Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen direktziehenden Azofarbstoff ge- langt, wenn man eine Diazoverbindung des Aminomonoazofarbstoffes der Formel
EMI0001.0007
mit 2-Phenylamino-5-oxynaphthalin-7-sulfon- säure-3'-carbonsä.ure kuppelt und den so er haltenen Disazofarbstoff in der Weise mit kupferabgebenden Mitteln behandelt,
dass un ter Aufspaltung der -0-Alkyl-Gruppe der o,o'-Dioxyazo-Kupferkomplex entsteht. Der neue Farbstoff bildet ein dunkles Pul ver, das sich in Wasser mit blaugrüner Farbe löst und Baumwolle in blaugrünen Tönen von hervorragender Lichtechtheit färbt. Der Aminomonoazofarbstoff der obigen Formel wird zweckmässig durch Kupplung von dianotierter 4-Aminostilben-2,2'-disulfon- säure mit. 1-Amino-2-methoxynaphthalin-6-sul- fonsäure in saurem bis neutralem Medium erhalten.
Die Kupplung der Diazoazoverbin- dung mit der 2-Phenylamino-5-oxynaphthalin- 7-sulfonsäure-3'-carbonsäure erfolgt mit Vor teil in alkalischem Medium, und es empfiehlt sich, ein die Kupplung förderndes Mittel, z. B. Pyridin, zuzusetzen.
Die 4-Aminostilben-2,2'- disulfonsUux,e lä.sst sich aus 4-Nitro-4'-amino- stilben-2,2'-disulfonsäure durch Diazotieren, Ersatz der Diazogruppe durch ein Wasser stoffatom und Reduktion der Nitrogruppe nach an sich bekannten Methoden herstellen.
Die Kupferung erfolgt zweckmässig wäh rend mehrerer Stunden in der Nähe von 100 in wässerigem, beispielsweise schwach saurem, Medium.
<I>Beispiel:</I> 35,5 Teile 4-Aminostilben-2,2'-disulfonsäure werden in 150 Teilen Wasser und 11 Teilen wasserfreiem Natriumcarbonat gelöst, mit 25 Teilen 30 % iger Salzsäure angesäuert und mit 6,9 Teilen Natriumnitrit in 50 Teilen Wasser dianotiert.
Die mit Natriumbicarbonat schwach kongoviolett gestellte Diazolösung wird mit 25,3 Teilen 1-Amino-2-methoxynaphthalin-6- sulfonsäure, die als Natriumsalz mit 20 Tei len krist. Natriumacetat in 200 Teilen Wasser gelöst wurden, gekuppelt.
Nach beendeter Kupplung wird der Disazofarbstoff mit Na- triumcarbonat alkalisch gemacht, ausgesalzen und abfiltriert. Er wird in 1000 Teilen Wasser gelöst,
mit 7 Teilen Natriumnitrit versetzt und durch Zugabe von 40 Teilen 30 % iger Salzsäure diazotiert. Man rührt noch 2 Stun den bei 15 und trägt die Diazoverbindung in eine kalte Lösung aus<B>35,
9</B> Teilen 2-Phenyl- amino - 5 - oxy naphthalin - 7 -sulfonsäure-3'-car- bonsäure, 40 Teilen Natriumacetat und 100 Teilen Pyridin in 200 Teilen Wasser ein.
Nach beendeter Kupplung wird der Disazofarbstoff ausgesalzen, abfiltriert und zwecks überfüh- rung in den Kupferkomplex 5 Stunden mit 25 Teilen krist. Kupfersulfat und 15 Teilen Natriumacetat in 2000 Teilen Wasser am Rückfluss gekocht. Der mit. Natriumehlorid abgeschiedene Kupferkomplex wird abfiltriert und nach bekannter Methode in das Natrium salz übergeführt.
<B> Additional patent </B> to 13th main patent No. 303281. Process for the production of a direct azo dye. It has been found that a valuable substantive azo dye is obtained if one uses a diazo compound of the aminomonoazo dye of the formula
EMI0001.0007
coupling with 2-phenylamino-5-oxynaphthalene-7-sulfonic acid-3'-carboxylic acid and treating the disazo dye obtained in this way with copper-donating agents,
that under splitting of the -0-alkyl group of the o, o'-dioxyazo copper complex is formed. The new dye forms a dark powder that dissolves in water with a blue-green color and dyes cotton in blue-green shades of excellent lightfastness. The amino monoazo dye of the above formula is expediently made by coupling dianotated 4-aminostilbene-2,2'-disulfonic acid with. 1-Amino-2-methoxynaphthalene-6-sulphonic acid obtained in an acidic to neutral medium.
The coupling of the diazoazo compound with the 2-phenylamino-5-oxynaphthalene-7-sulfonic acid-3'-carboxylic acid takes place in an alkaline medium with advantage, and it is advisable to use an agent promoting the coupling, eg. B. pyridine to add.
The 4-aminostilbene-2,2'-disulfonic acid can be obtained from 4-nitro-4'-aminostilbene-2,2'-disulfonic acid by diazotizing, replacing the diazo group with a hydrogen atom and reducing the nitro group produce known methods.
The coppering takes place expediently for several hours in the vicinity of 100 in an aqueous, for example weakly acidic medium.
<I> Example: </I> 35.5 parts of 4-aminostilbene-2,2'-disulfonic acid are dissolved in 150 parts of water and 11 parts of anhydrous sodium carbonate, acidified with 25 parts of 30% hydrochloric acid and 6.9 parts of sodium nitrite dianotized in 50 parts of water.
The weakly congoviolet with sodium bicarbonate diazo solution is with 25.3 parts of 1-amino-2-methoxynaphthalene-6-sulfonic acid, which is crystal as the sodium salt with 20 parts. Sodium acetate were dissolved in 200 parts of water, coupled.
After the coupling has ended, the disazo dye is made alkaline with sodium carbonate, salted out and filtered off. It is dissolved in 1000 parts of water,
7 parts of sodium nitrite are added and the mixture is diazotized by adding 40 parts of 30% strength hydrochloric acid. The mixture is stirred for a further 2 hours at 15 and the diazo compound is added to a cold solution of <B> 35,
9 parts of 2-phenylamino-5-oxy naphthalene-7-sulfonic acid-3'-carboxylic acid, 40 parts of sodium acetate and 100 parts of pyridine in 200 parts of water.
After coupling has ended, the disazo dye is salted out, filtered off and, for the purpose of transferring it into the copper complex, with 25 parts of crystalline for 5 hours. Copper sulfate and 15 parts of sodium acetate are refluxed in 2000 parts of water. The one with. The copper complex deposited with sodium chloride is filtered off and converted into the sodium salt by a known method.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH306273T | 1951-11-12 | ||
| CH303281T | 1951-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306273A true CH306273A (en) | 1955-03-31 |
Family
ID=25734623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306273D CH306273A (en) | 1951-11-12 | 1951-11-12 | Process for the preparation of a substantive azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306273A (en) |
-
1951
- 1951-11-12 CH CH306273D patent/CH306273A/en unknown
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