CH228936A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH228936A CH228936A CH228936DA CH228936A CH 228936 A CH228936 A CH 228936A CH 228936D A CH228936D A CH 228936DA CH 228936 A CH228936 A CH 228936A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- mol
- carboxylic acid
- phosgene
- production
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 229920000742 Cotton Polymers 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
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001879 copper Chemical class 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
- 239000000843 powder Substances 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 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
- 235000010288 sodium nitrite Nutrition 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
Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Azofarbstoff erhält, wenn man 1 Mol diano tierte 1-Aminobenzol-2-carbonsäure, 1 Mol 2-(4'- Amino)-benzoylamino-5-oxynaphthalin- 7-sulfonsäure, 1 Mol Phosgen und 1 Mol 4-Amino-4'- oxy-1,1'- azobenzol-3'-carbonsäure derart aufeinander einwirken lässt,
dass die Diazoverbindung in 6-Stellung des Naphtha linkernes eingreift und das Phosgen die Aminogruppen der 2-(4'-Amino)-benzoyl- amino - 5 - oxynaphthalin- 7 -sulfonsäure und die 4-Amino-4'-oxy-1,1'-azobenzol-3'-carbon- säure unter Bildung eines gemischten Harn stoffderivates vereinigt.
Der neue Farbstoff stellt ein braunrotes Pulver dar und färbt Baumwolle in schwach alkalischem Bade, das mit einer Kupfersalz lösung aus Kupfersulfat und weinsaurem Na trium versetzt wurde, in wasch- und licht echten orangebraunen Tönen an. Beispiel: 13,7 Gewichtsteile 1-Aminobenzol-2-car- bonsäure werden in 200 Gewichtsteilen Was- ser mit Natronlauge neutral gelöst und mit 6,9 Gewichtsteilen Natriumnitrit und 25 Ge wichtsteilen konz. Salzsäure bei 5 dianotiert.
Nach 30 Minuten wird das entstandene Di- azoniumsalz mit<B>35,8</B> Gewichtsteilen 2-(4' Amino)-benzoylamino-5-ogynaphthalin-7-sul- fonsäure, die als Natriumsalz in 200 Ge wichtsteilen Wasser gelöst wurden, unter Zu satz von 30 Gewichtsteilen Natriumcarbonat und gegebenenfalls unter Zusatz von Fis bei 5 vereinigt. Nach 6 Stunden wird der ge bildete Monoazofarbstoff mit Kochsalz als Natriumsalz in der Wärme abgeschieden.
55 Gewichtsteile Dinatriumsalz des so erhal tenen Produktes werden mit 27,9 Gewichts teilen Natriumsalz der 4-Amino-4'-ogy-1;1'- azobenzol-3'-carbonsäure in 6000 Gewichts teilen Wasser unter Zusatz von 60 Gewichts teilen Natriumcarbonat gelöst und bei 30 bis 40 mit Phosgen behandelt, bis keine freie NH2-Gruppe mehr nachweisbar ist. Der ge bildete Harnstoff wird kongosauer abgeschie den, unter Zusatz von Natronlauge gelöst und der Farbstoff als Natriumsalz mit Koch salz abgeschieden und getrocknet.
Zum gleichen Farbstoff gelangt man auch, wenn man zunächst aus 1 Mol 2-(4' Amino)-benzoylamino-5-oxynaphthalin-7-sul- fonsäure und 1 Mol 4-Amino-4'-oxy-1,1'-a,zo- benzol-3'-carbonsäure und Phosgen einen ge mischten Harnstoff herstellt und diesen mit 1 Mol der diazotierten 1-Aminobenzol-2-ca.r- bonsäure vereinigt.
Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1 mol of diano-oriented 1-aminobenzene-2-carboxylic acid, 1 mol of 2- (4'-amino) -benzoylamino-5-oxynaphthalene-7-sulfonic acid, 1 mol of phosgene and 1 mol of 4-amino-4'-oxy-1,1'-azobenzene-3'-carboxylic acid can act on one another in such a way that
that the diazo compound intervenes in the 6-position of the naphtha linkernes and the phosgene the amino groups of 2- (4'-amino) -benzoyl-amino-5-oxynaphthalene-7-sulfonic acid and 4-amino-4'-oxy-1, 1'-azobenzene-3'-carboxylic acid combined to form a mixed urea derivative.
The new dye is a brown-red powder and dyes cotton in a weakly alkaline bath to which a copper salt solution of copper sulfate and tartaric sodium has been added in washable and light orange-brown tones. Example: 13.7 parts by weight of 1-aminobenzene-2-carboxylic acid are dissolved neutrally in 200 parts by weight of water with sodium hydroxide solution and 6.9 parts by weight of sodium nitrite and 25 parts by weight of conc. Hydrochloric acid dianotized at 5.
After 30 minutes, the diazonium salt formed is dissolved with 35.8 parts by weight of 2- (4 'amino) benzoylamino-5-ogynaphthalene-7-sulphonic acid, the sodium salt, in 200 parts by weight of water were combined with the addition of 30 parts by weight of sodium carbonate and optionally with the addition of Fis at 5. After 6 hours, the monoazo dye formed is deposited in the heat with common salt as the sodium salt.
55 parts by weight of the disodium salt of the product obtained in this way are dissolved with 27.9 parts by weight of the sodium salt of 4-amino-4'-ogy-1; 1'-azobenzene-3'-carboxylic acid in 6000 parts by weight of water with the addition of 60 parts by weight of sodium carbonate and treated with phosgene at 30 to 40 until no more free NH2 groups can be detected. The urea formed is deposited in Congo acid, dissolved with the addition of sodium hydroxide solution and the dye deposited as the sodium salt with sodium chloride and dried.
The same dye can also be obtained if 1 mol of 2- (4 'amino) benzoylamino-5-oxynaphthalene-7-sulphonic acid and 1 mol of 4-amino-4'-oxy-1,1'-a , zobenzene-3'-carboxylic acid and phosgene produces a mixed urea and combines this with 1 mole of the diazotized 1-aminobenzene-2-carboxylic acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228936T | 1942-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH228936A true CH228936A (en) | 1943-09-30 |
Family
ID=4455829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228936D CH228936A (en) | 1942-07-03 | 1942-07-03 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH228936A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE943661C (en) * | 1952-01-17 | 1956-05-24 | Sandoz Ag | Process for the production of disazo and polyazo dyes |
-
1942
- 1942-07-03 CH CH228936D patent/CH228936A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE943661C (en) * | 1952-01-17 | 1956-05-24 | Sandoz Ag | Process for the production of disazo and polyazo dyes |
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