CH214824A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH214824A CH214824A CH214824DA CH214824A CH 214824 A CH214824 A CH 214824A CH 214824D A CH214824D A CH 214824DA CH 214824 A CH214824 A CH 214824A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- amino
- trisazo
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 14
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 229920000297 Rayon Polymers 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001844 chromium Chemical class 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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
- 239000000243 solution Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- IZNPFDIKQHGNSK-UHFFFAOYSA-N 5-amino-6-ethoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OCC)=CC=C21 IZNPFDIKQHGNSK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B31/16—Trisazo dyes
- C09B31/22—Trisazo dyes from a coupling component "D" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 212422. Verfahren zur Herstellung eines Trisazofarbstoffes. Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung eines Trisazo-
EMI0001.0003
mit N-4'-Oxy-3'-earboxyphenyl-1'-sulfonyl- N - methyl-2-amino-5-oxynaphthalin-7-sulf on- säure kuppelt.
EMI0001.0009
farbstoffes, bei dem man .die Diazoverbin- dung des Aminodisazofarbstoffes der Formel Es wurde nun gefunden, dass man einen neuen, ebenfalls wertvollen Trisazofarbstoff erhält,
wenn man die Diazoverbindung des Aminodisazofarbstoffes der Formel mit N-4'-Oxy-3'-carboxyphenyl-1'-sulfonyl- N- methyl-2-amino-5-oxynaphtha.lin-7-sulf on- säure (entsprechend der Formel
EMI0002.0006
kuppelt.
Der neue Trisazofarbstoff färbt. in grü nen Tönen, zieht substantiv auf Baumwolle, Viskoseseide und Leinen und lässt sich im Gemisch mit Wollfarbstoffen zum Färben von Wolle-Baumwolle- oder Wolle-Viskose- kunstseidemischungen verwenden. Die Echt heit der Färbungen kann durch Nachbehan deln mit Kupfer- oder Chromsalzlösungen noch verbessert werden.
<I>Beispiel:</I> Man kuppelt die Diazoverbindung aus 352 Teilen 3'-Aminobenzoyl - 1 - amino - 3 - ca.rboxy-4-oxybenzol-5-sulfonsäure mit 189 Teigen i - (4'- Aminophenyl)-3-methyl-5-py r a.zolon unter Zugabe von Natriumacetat. Nach Beendigung der Farbstoffbildung löst man die ockergelbe Masse mit Natronlauge auf, setzt 69 Teile Natriumnitrit zu und lässt bei 15 C langsam bis zur schwach sauren Reaktion Salzsäure zulaufen.
Man rührt. die dicke ora.ngebraune Masse einige Stunden lang nach und setzt dann eine neutrale Lö sung von 267 Teilen 1-Amino-2-äthoxynaph- thalin-6-sulfonsäure hinzu. Die Kupplung wird unter Zusatz von Natriumacetat zu Ende geführt. Sodann löst man. die Farb säure mit Natronlauge, salzt aus und saugt den Disazofarbstoff ab. Darauf nimmt man mit Wasser auf, setzt 69 Teile Natrium nitrit hinzu und diazotiert bei etwa 8 C durch langsame Zugabe von Salzsäure.
Da nach kuppelt man mit 453 Teilen N-4'-Oxy- 3'- earboxyphenyl -1'- sulfonyl - N - methyl - 2- amino - 5 - oxynaphthalin - 7 - sulfonsä,ure in ammoniakalischer, pyridinhaltiger Lösung.
<B> Additional patent </B> to main patent no. 212422. Process for the production of a trisazo dye. The subject of the main patent is a process for the production of a trisazo
EMI0001.0003
with N-4'-oxy-3'-earboxyphenyl-1'-sulfonyl-N-methyl-2-amino-5-oxynaphthalene-7-sulfonic acid.
EMI0001.0009
dye in which one .die diazo compound of the amino disazo dye of the formula It has now been found that a new, likewise valuable trisazo dye is obtained,
if the diazo compound of the aminodisazo dye of the formula with N-4'-oxy-3'-carboxyphenyl-1'-sulfonyl-N-methyl-2-amino-5-oxynaphtha.lin-7-sulfonic acid (corresponding to the formula
EMI0002.0006
clutch.
The new trisazo dye stains. in green tones, draws substantive to cotton, viscose silk and linen and can be used in a mixture with wool dyes to dye wool-cotton or wool-viscose rayon blends. The authenticity of the colorations can be improved by post-treating with copper or chromium salt solutions.
<I> Example: </I> The diazo compound is coupled from 352 parts of 3'-aminobenzoyl - 1 - amino - 3 - about rboxy-4-oxybenzene-5-sulfonic acid with 189 doughs i - (4'-aminophenyl) - 3-methyl-5-py r a.zolon with addition of sodium acetate. When the dye formation has ended, the ocher-yellow mass is dissolved with sodium hydroxide solution, 69 parts of sodium nitrite are added and hydrochloric acid is slowly added at 15 ° C. until a weakly acidic reaction occurs.
One stirs. the thick orange-brown mass for a few hours and then adds a neutral solution of 267 parts of 1-amino-2-ethoxynaphthalene-6-sulfonic acid. The coupling is brought to an end with the addition of sodium acetate. Then you solve. the color acid with sodium hydroxide solution, salt out and sucks off the disazo dye. It is then taken up in water, 69 parts of sodium nitrite are added and the mixture is diazotized at about 8 ° C. by slowly adding hydrochloric acid.
Then coupling is carried out with 453 parts of N-4'-oxy-3'-earboxyphenyl -1'-sulfonyl-N-methyl-2-amino-5-oxynaphthalene-7-sulfonic acid in an ammoniacal, pyridine-containing solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE214824X | 1938-07-23 | ||
| CH212422T | 1939-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH214824A true CH214824A (en) | 1941-05-15 |
Family
ID=25725262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH214824D CH214824A (en) | 1938-07-23 | 1939-06-22 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH214824A (en) |
-
1939
- 1939-06-22 CH CH214824D patent/CH214824A/en unknown
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