CH231402A - Process for the preparation of a polyazo dye. - Google Patents
Process for the preparation of a polyazo dye.Info
- Publication number
- CH231402A CH231402A CH231402DA CH231402A CH 231402 A CH231402 A CH 231402A CH 231402D A CH231402D A CH 231402DA CH 231402 A CH231402 A CH 231402A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- amino
- acid
- sulfonic acid
- oxybenzene
- Prior art date
Links
- -1 polyazo Polymers 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 15
- 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 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 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
- 239000002253 acid Substances 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 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
- 125000001624 naphthyl group Chemical group 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000000203 mixture Substances 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
- 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
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 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
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 228437. Verfahren zur Herstellung eines Polyazofarbstoifes. Es wurde gefunden, dass man zu einem neuen Polyazofarbstoff gelangt, wenn man 1 Mol 2-Amino-5-oxynaphthalin-7-sulfonsäure, 1 Mol 1- Amino- 4 -oxybenzol- 3 -carbonsäure, 1 Mol Phosgen und 1 Mol des diazotierten Disazofarbstoffes,
der selbst erhältlich ist durch Vereinigen der Diazoverbindung der 1-Amino- 4-oxybenzol-3-carbonsäure mit 1-Aminonaph- thalin-7-sulfonsäure, Diazotieren des so ent standenen Monoazofarbstoffes und Vereinigen mit einem weiteren Mol 1-Aminonaphthalin- 7-sulfonsäure, derart aufeinander einwirken lässt,
dass einerseits die Diazoverbindung in 6-Stellung des Naphthalinkerns der Amino- naphtholsulfonsäure eingreift und anderseits das Phosgen mit der Aminogruppe des Amino- naphthol-Derivates und der Aminogruppe der 1-Amino-4-oxybenzol-3-carbonsäure unter Bil dung eines gemischten Harnstoff -Derivates reagiert.
Der neue Polyazofarbstoff stellt ein dunkles Pulver dar, das Baumwolle in schwach alka lischem Bade bei Gegenwart von Kupfersulfat und weinsaurem Natrium in waschechten, grauen Tönen färbt. .
<I>. Beispiel:</I> 15,3 Gew:-Teile 1-Amino- 4 -oxybenzol- 3- carbonsäure werden in üblicher Weise diazo- tiert und bei Gegenwart von Natriumacetat mit 22,3 Gew.-Teilen 1-Aminonaphthalin-7- sulfonsäure, die als Natriumsalz in 200 Gew.- Teilen Wasser gelöst wurden, bei 0 gekup pelt.
Der sich abscheidende Konoazofarbstoff wird dann mit wässeriger Natronlauge in Lösung gebracht, mit 6,9 Gew.-Teilen Na= triumnitrit in 25 o/oiger wässeriger Lösung versetzt und das Gemisch zu einer Mischung von 200 Gew.-Teilen Eiswasser und 50 Gew.- Teilen konz. Salzsäure zulaufen gelassen.
Ist die Diazotierung, die bei 0-5 o durchgeführt wird, beendet, so wird die mittels Kochsalz abgeschiedene Diazoverbindung abgesaugt und mit weiteren 22,3 Gew.-Teilen 1-Aminonaph- thalin-7-sulfonsäure, die als Natriumsalz in 200 Gew.-Teilen Wasser gelöst wurden, ver- einigt. Während der Kupplung werden 20 Gew.-Teile Natriumacetat eingestreut und das Produkt nach einiger Zeit mit Kochsalz ab geschieden.
Es wird mit etwas Natronlauge in Lösung gebracht, mit 6,9 Gew.-Teilen Natriumnitrit in 25 /oiger Lösung versetzt und dieses Gemisch mit einer 1U, ischung von 200 Gew.-Teilen Eiswasser und 50 Gew.- Teilen konz. Salzsäure bei 15 o weiter diazo- tiert. Die abgeschiedene Diazoverbindung wird alsdann mit 41,
8 Gew.-Teilen des in bekann ter ZVeise mit Phosgen hergestellten Harn stoffes aus äquimolekularen Mengen von 2- Amino- 5 -oxyiiaphthalin-7-sulfonsäure und 1 Amino-4-oxybenzol-3-carbonsäure in sodaalka- lischer Lösung vereinigt.
Nach beendeter Kupplung wird der Farb stoff abgeschieden und getrocknet.
Zu demselben Produkt gelangt man, wenn man den diazotierten Disazofarbstoff mit 1Mol 2 -Amino- 5 -oxynaphthalin-7- sulfonsäure ver einigt und 1 Dlol des erhaltenen Trisazofarb- stoffes mit Hilfe von Phosgen mit 1 11o1 1- Amino-3-carboxy-4-oxybenzol zu einem asym metrischen Harnstoff vereinigt.
Additional patent to main patent no. 228437. Process for the production of a polyazo dye. It has been found that a new polyazo dye is obtained if 1 mole of 2-amino-5-oxynaphthalene-7-sulfonic acid, 1 mole of 1-amino-4-oxybenzene-3-carboxylic acid, 1 mole of phosgene and 1 mole of the diazotized Disazo dye,
which is itself obtainable by combining the diazo compound of 1-amino-4-oxybenzene-3-carboxylic acid with 1-aminonaphthalene-7-sulfonic acid, diazotizing the monoazo dye thus formed and combining with a further mole of 1-aminonaphthalene-7-sulfonic acid to interact in such a way that
that on the one hand the diazo compound intervenes in the 6-position of the naphthalene nucleus of the amino naphtholsulfonic acid and on the other hand the phosgene with the amino group of the amino naphthol derivative and the amino group of the 1-amino-4-oxybenzene-3-carboxylic acid to form a mixed urea - Derivatives reacts.
The new polyazo dye is 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: 15.3 parts by weight of 1-amino-4-oxybenzene-3-carboxylic acid are diazo- tated in the usual manner and, in the presence of sodium acetate, with 22.3 parts by weight of 1-aminonaphthalene-7- sulfonic acid, which was dissolved as the sodium salt in 200 parts by weight of water, kup pelt at 0.
The Konoazo 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 added to a mixture of 200 parts by weight of ice water and 50 parts by weight. Share conc. Allowed hydrochloric acid to run in.
When the diazotization, which is carried out at 0-5 o, has ended, 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-aminonaphthalene-7-sulfonic acid, which is dissolved as the sodium salt in 200 wt. Parts of water were dissolved, combined. During the coupling, 20 parts by weight of sodium acetate are sprinkled in and the product is separated after some time with common salt.
It is brought into solution with a little sodium hydroxide solution, 6.9 parts by weight of sodium nitrite in 25% solution are added and this mixture is mixed with a 1U of 200 parts by weight of ice water and 50 parts by weight of conc. Hydrochloric acid further diazotized at 15 o. The separated diazo compound is then called 41,
8 parts by weight of the urea prepared in known ZVeise with phosgene from equimolecular amounts of 2-amino-5-oxyiiaphthalene-7-sulfonic acid and 1 amino-4-oxybenzene-3-carboxylic acid combined in a soda-alkali solution.
After the coupling is complete, the dye is deposited and dried.
The same product is obtained if the diazotized disazo dye is combined with 1 mol of 2-amino-5-oxynaphthalene-7-sulfonic acid and 1 dole of the trisazo dye obtained with 11o1 1-amino-3-carboxy-4 using phosgene -oxybenzene combined to form an asymmetrical urea.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228437T | 1942-04-02 | ||
| CH231402T | 1942-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH231402A true CH231402A (en) | 1944-03-15 |
Family
ID=25727209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH231402D CH231402A (en) | 1942-04-02 | 1942-04-02 | Process for the preparation of a polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH231402A (en) |
-
1942
- 1942-04-02 CH CH231402D patent/CH231402A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH231402A (en) | Process for the preparation of a polyazo dye. | |
| CH231404A (en) | Process for the preparation of a polyazo dye. | |
| CH231406A (en) | Process for the preparation of a polyazo dye. | |
| CH231408A (en) | Process for the preparation of a polyazo dye. | |
| CH231407A (en) | Process for the preparation of a polyazo dye. | |
| CH231403A (en) | Process for the preparation of a polyazo dye. | |
| CH643867A5 (en) | METHOD FOR PRODUCING azo dyes. | |
| CH248706A (en) | Process for the preparation of a trisazo dye. | |
| CH231405A (en) | Process for the preparation of a polyazo dye. | |
| CH248708A (en) | Process for the preparation of a trisazo dye. | |
| DE917990C (en) | Process for the preparation of new trisazo dyes | |
| DE844772C (en) | Process for the preparation of trisazo dyes | |
| DE762865C (en) | Process for the preparation of trisazo dyes | |
| AT115627B (en) | Process for the preparation of polyazo dyes. | |
| CH224547A (en) | Process for the production of a copper-containing trisazo dye. | |
| CH249545A (en) | Process for the preparation of a trisazo dye. | |
| CH148005A (en) | Process for the preparation of a disazo dye. | |
| CH248707A (en) | Process for the preparation of a trisazo dye. | |
| CH228437A (en) | Process for the preparation of a polyazo dye. | |
| CH148003A (en) | Process for the preparation of a disazo dye. | |
| CH305336A (en) | Process for the production of a copper-containing trisazo dye. | |
| CH132807A (en) | Process for the preparation of a new green tetrakisazo dye. | |
| CH293888A (en) | Process for the production of a copper-containing polyazo dye. | |
| CH244053A (en) | Process for the preparation of a trisazo dye. | |
| CH289588A (en) | Process for the preparation of a polyazo dye. |