CH248706A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH248706A CH248706A CH248706DA CH248706A CH 248706 A CH248706 A CH 248706A CH 248706D A CH248706D A CH 248706DA CH 248706 A CH248706 A CH 248706A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- dye
- weight
- parts
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 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 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 239000000203 mixture Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 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
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 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 description 1
- 239000000047 product 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. 244053. Verfahren zur Herstellung eines Trisazofarbatoffes. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Herstellung eines Trisazofarbstoffes, dadurch gekenn- zeichnet, dass der dianotierte Disazofarbstoff der Formel .
EMI0001.0007
mit dem Lernären Triazinkondensationspro- dukt aus 1 Mol Cyanurchlorid, 1 Mol 2- Amino-5-oxynaphthalin-7-sulfonsäure, 1 Mol 1-Aminobenzol-3-sulfonsäure und 1 Mol 1- Aminobenzol in alkalischer Lösung vereinigt wird.
Der neue Farbstoff bildet ein dunkles Pulver, das Baumwolle in schwach alkali schem Bade bei Gegenwart von Kupfersulfat und weinsaurem Natrium in waschechten grauen Tönen färbt.
<I>Beispiel:</I> 15,3 Gew.-Teile 1-Amino-3-carboxy-4- oxybenzol werden in üblicher Weise diazo- tiert und bei Gegenwart von Natriumacetat mit 22,3 Gew.-Teilen 1-Naphthyla.min-7-sul- fonsäure, die als Natriumsalz in 200 Gew.- Teilen Wasser gelöst wurden, bei 0 gekup pelt.
Der sich abscheidende Monoazofarbstoff wird dann mit wässeriger Natronlauge in Lösung gebracht, mit 6,9 Gew.-Teilen Na triumnitrit in 25%iger wässeriger Lösung versetzt und das Gemisch zu einem Mischung von 200 Gew.-Teilen Eiswasser und 50 Gew.- Teilen konz. Salzsäure zulaufen gelassen.
Ist die Dianotierung, die bei 0-5 durchgeführt wird, beendet, so wird die mittels Kochsalz abgeschiedene Diazoverbindung abgesaugt und mit weiteren 22,3 Gew.-Teilen 1-Naph- thylamin-7-sulfonsäure, die als Natriumsalz in 200 Gew.-Teilen Wasser gelöst wurden, vereinigt.
Während der Kupplung werden 20 Gew.-Teile Natriumacetat eingestreut und das Produkt nach einiger Zeit mit Kochsalz abgeschieden. Es wird mit etwas Natronlauge in Lösung gebracht, mit 6,
9 Gew.-Teilen Natriumnitrit in 25%iger Lö sung versetzt und dieses Gemisch mit einer Mischung von 200 Gew.-Teilen Eiswasser und 50 Gew.-Teilen konz. Salzsäure bei 1.5 weiter dianotiert. Die abgeschiedene Di- azoverbindung wird alsdann mit 58 Gew.- Teilen des in bekannter Weise hergestellten ternä,
ren Triazinkondensationsproduktes aus 1. Mol Cyanurchlorid, 1 Mol 2-Amino-5-oxy- naphthalin-7-sulfonsäure, 1 Mol 1-Aminoben- zol-3-sulfonsäure und 1 Mol 1-Aminobenzol in soloalkalischer Lösung vereinigt. Nach beendeter Kupplung wird der Farbstoff ab- geschieden und getrocknet.
Additional patent to main patent No. 244053. Process for the production of a trisazo carbate. The subject of the present additional patent is a process for the production of a trisazo dye, characterized in that the dianotated disazo dye of the formula.
EMI0001.0007
is combined with the learning triazine condensation product of 1 mol of cyanuric chloride, 1 mol of 2-amino-5-oxynaphthalene-7-sulfonic acid, 1 mol of 1-aminobenzene-3-sulfonic acid and 1 mol of 1-aminobenzene in an alkaline solution.
The new dye forms a dark powder that dyes cotton in a weakly alkaline bath in the presence of copper sulfate and tartrate of sodium in washfast gray tones.
<I> Example: </I> 15.3 parts by weight of 1-amino-3-carboxy-4-oxybenzene are diazotized in the customary manner and, in the presence of sodium acetate, with 22.3 parts by weight of 1-naphthyla .min-7-sulphonic acid, which was dissolved as the sodium salt in 200 parts by weight of water, kup pelt at 0.
The monoazo dye which separates out is then brought into solution with aqueous sodium hydroxide solution, 6.9 parts by weight of sodium nitrite in 25% aqueous solution are added and the mixture is concentrated to a mixture of 200 parts by weight of ice water and 50 parts by weight . Allowed hydrochloric acid to run in.
When the dianotation, which is carried out at 0-5, is complete, the diazo compound deposited by means of sodium chloride is filtered off with suction and treated with a further 22.3 parts by weight of 1-naphthylamine-7-sulfonic acid, which is dissolved as the sodium salt in 200% by weight. Parts of water were dissolved, combined.
During the coupling, 20 parts by weight of sodium acetate are sprinkled in and the product is separated out after some time with common salt. It is brought into solution with a little sodium hydroxide solution, with 6,
9 parts by weight of sodium nitrite in 25% solution are added and this mixture with a mixture of 200 parts by weight of ice water and 50 parts by weight of conc. Hydrochloric acid further dianotized at 1.5. The deposited diazo compound is then mixed with 58 parts by weight of the ternary prepared in a known manner,
Ren triazine condensation product from 1st mole of cyanuric chloride, 1 mole of 2-amino-5-oxynaphthalene-7-sulfonic acid, 1 mole of 1-aminobenzene-3-sulfonic acid and 1 mole of 1-aminobenzene combined in sol-alkaline solution. After the coupling has ended, the dye is deposited and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244053T | 1945-06-21 | ||
| CH248706T | 1945-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH248706A true CH248706A (en) | 1947-05-15 |
Family
ID=25728903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH248706D CH248706A (en) | 1945-06-21 | 1945-06-21 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH248706A (en) |
-
1945
- 1945-06-21 CH CH248706D patent/CH248706A/en unknown
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