CH236528A - Process for the preparation of a polyazo dye. - Google Patents
Process for the preparation of a polyazo dye.Info
- Publication number
- CH236528A CH236528A CH236528DA CH236528A CH 236528 A CH236528 A CH 236528A CH 236528D A CH236528D A CH 236528DA CH 236528 A CH236528 A CH 236528A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- amino
- diaminostilbene
- azobenzene
- oxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 polyazo Polymers 0.000 title description 4
- 239000000975 dye Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- REJHVSOVQBJEBF-UHFFFAOYSA-N 5-azaniumyl-2-[2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 claims description 2
- 229920002955 Art silk Polymers 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 2338,45. Verfahren zur Herstellung eines Polyazofarbstoffes: Es wurde gefunden, dass man einen neuen Polyazofarbstoff erhält, wenn man 1 Mol 4.4'-Diaminostilben-2.2'-disulfonsäure,
2 Mol Cyanurchlorid und 4 Mol 2-Methyl-4-amino- 5 - methoxy - 4'- oxy - 1.1i - azobenzol-3'-carbon- säure derart aufeinander einwirken lässt,
dass je 2 Halogenatome der beiden CyanurcIllorid- moleküle sich mit der Aminogruppe der 2- Methyl - 4 - amino -j5 - methoxy-4'-oxy-1.1'-azo- benzol-3(-carbonsäure umsetzen, und dass je weils das dritte Halogenatom der beiden Cyanurchloridmoleküle sich jeweils mit einer Aminogruppe der 4.4'-Diaminostilben-2.2'-di- sulfonsäure umsetzt.
Der neue Farbstoff stellt getrocknet ein bräunliches Pulver dar, welches sich in ver dünnter Natriumhydroxydlösung mit gelb brauner, in konzentrierter Schwefelsäure mit tiefbrauner Farbe löst und welches die vege- tabile Faser sowie Kunstseide aus regenerier ter Cellulose in gelben Tönen anfärbt, welche durch Nachbehandeln mit kupferabgebenden Mitteln im Färbebad hervorragend waschecht werden. <I>Beispiel:</I> Man stellt in an sich bekannter Weise eine feine Suspension von 36,8 Teilen Cyanurchlo- rid in 400- Teilen Eiswasser dar.
Zu dieser Suspension gibt man eine Lösung von 37 Tei len 4.4'-Diaminostilben-2.2'-disulfonsäure (als Dinatriumsalz) in 600 Teilen Wasser zu. Das Kondensationsprodukt aus 1 Äquivalent Di- aminostilbendisulfonsäure und 2 Äquivalen ten Cyanurchlorid fällt in Form blassgelber gallertiger Suspension zum grossen Teil aus. Man rührt noch zirka eine Stunde bei 0-5 unter gleichzeitigem Zutropfen einer Lösung von 15 Teilen Natriumcarbonat in 150 Teilen Wasser.
Alsdann gibt man eine warme Lö sung des Natriumsalzes von 120,4 Teilen 2- Methyl -,4 - amino -'5 - inethoxy-4'-oxy-1.1'-azo- benzol-3'-carbonsäure in zirka 1500 Teilen Wasser zu.
Man erwärmt das Gemisch auf etwa 40-45 , hält diese Temperatur 2 Stun den, stumpft die freiwerdende Säure wäh rend ihrer Entstehung mit Natriumcarbonat- lösung ab, steigert alsdann die Temperatur auf zirka 95 und hält diese Temperatur 2 Stunden unter weiterer Zugabe von 22 Teilen Natriumcarbonat. Man lässt erkal- ten und salzt den Farbstoff der mutmasslichen ao Formel
EMI0002.0004
durch Zugabe von 50 Teilen Kochsalz aus, lä.sst auf zirka 50 erkalten und nutscht den Farbstoff ab.
Additional patent to main patent no. 2338.45. Process for the preparation of a polyazo dye: It has been found that a new polyazo dye is obtained if 1 mole of 4,4'-diaminostilbene-2.2'-disulfonic acid,
2 moles of cyanuric chloride and 4 moles of 2-methyl-4-amino-5-methoxy-4'-oxy-1.1i-azobenzene-3'-carboxylic acid can act on one another in such a way that
that every 2 halogen atoms of the two cyanuric chloride molecules react with the amino group of the 2-methyl-4-amino-j5-methoxy-4'-oxy-1.1'-azobenzene-3 (-carboxylic acid, and that in each case the third Halogen atom of the two cyanuric chloride molecules each reacts with an amino group of 4.4'-diaminostilbene-2.2'-disulfonic acid.
The new dye is a brownish powder when dried, which dissolves in dilute sodium hydroxide solution with yellow-brown, in concentrated sulfuric acid with a deep brown color and which dyes the vegetable fibers and artificial silk made of regenerated cellulose in yellow tones, which are colored by post-treatment with copper-releasing substances Agents in the dye bath are extremely washable. <I> Example: </I> A fine suspension of 36.8 parts of cyanuric chloride in 400 parts of ice water is prepared in a manner known per se.
A solution of 37 parts of 4.4'-diaminostilbene-2.2'-disulfonic acid (as disodium salt) in 600 parts of water is added to this suspension. The condensation product of 1 equivalent of diaminostilbene disulfonic acid and 2 equivalents of cyanuric chloride precipitates for the most part in the form of pale yellow gelatinous suspension. The mixture is stirred for about an hour at 0-5 with simultaneous dropwise addition of a solution of 15 parts of sodium carbonate in 150 parts of water.
A warm solution of the sodium salt of 120.4 parts of 2-methyl-, 4-amino -'5-ynethoxy-4'-oxy-1.1'-azobenzene-3'-carboxylic acid in about 1500 parts of water is then added .
The mixture is heated to about 40-45, this temperature is maintained for 2 hours, the acid released is blunted with sodium carbonate solution as it is formed, the temperature is then increased to about 95 and this temperature is maintained for 2 hours with further addition of 22 parts Sodium. Let it cool down and salt the dye of the presumed ao formula
EMI0002.0004
by adding 50 parts of table salt, lets it cool to about 50 and sucks off the dye.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH236528T | 1942-09-29 | ||
| CH233845T | 1942-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH236528A true CH236528A (en) | 1945-02-15 |
Family
ID=25727816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236528D CH236528A (en) | 1942-09-29 | 1942-09-29 | Process for the preparation of a polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH236528A (en) |
-
1942
- 1942-09-29 CH CH236528D patent/CH236528A/en unknown
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