CH285002A - Process for the preparation of a copper-compatible tetrakisazo dye. - Google Patents
Process for the preparation of a copper-compatible tetrakisazo dye.Info
- Publication number
- CH285002A CH285002A CH285002DA CH285002A CH 285002 A CH285002 A CH 285002A CH 285002D A CH285002D A CH 285002DA CH 285002 A CH285002 A CH 285002A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- dye
- copper
- preparation
- compatible
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000975 dye Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/40—Trisazo dyes ot the type the component K being a dihydroxy or polyhydroxy compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 282092. Verfahren zur Herstellung eines kupferbaren Tetrakisazofarbstoffes. \ Gegenstand. vorliegenden Patentes ist ein Verfahren zur Herstellung eines kupferbaren Tetrakisazofarbstoffes. Das Verfahren ist da durch -ekennzeiehnet, dass man 1 Mol der
EMI0001.0006
und anderseits mit 1 Mol 3-Methyl-5-pyrazolon vereinigt.
1-.)ei- erhaltene nette Tetrakisazofarbstoff stellt ein dunkles Pulver dar und löst sich in Wasser und konz. Schwefelsäure mit brauner Farbe.
<I>Beispiel:</I> Man dianotiert 17,2 Teile 1-Arrrinobenzol-3- sulfonsäure mit 6,9 Teilen Natriumnitrit in bekannter Weise und kuppelt in Anwesen- heit von 14,6 Teilen 30%iger Natronlauge und 25 Teilen Natriumcarbonat mit 16,0 Teilen 1-Acetylarnino-2-oxy-benzol. Ist die Kupplung fertig, wird der Farbstoff durch Erhitzen mit verdünnter Natronlauge verseift, mit,
verdünn ter Sehwefelsäure kalt ausgefällt und abfil- triert. Man löst nun den Farbstoff in Wasser und 17 Teilen 30%iger Natronlauge, versetzt mit 20% Kochsalz und dianotiert in der Kälte mit 7,7 Teilen Natriumnitrit und 50 Teilen Salzsäure (d :
l,16). Die Diazoniumverbindung wird abfiltriert und in Anschlämmung mit 11,0 Teilen 1.,3-Dioxy-benzol in Gegenwart von 40 Teilen Natriumcarbonat gekuppelt.
Den Disazofarbstoff säuert man mit 125 Teilen Tetrazoverbindung von 1-(4'-Arnino-benzoyl- amino)-4-amino-benzol einerseits mit 1 Mol des Disazofarbstoffes der Formel Salzsäure (d :
1,1.6) aus, filtriert und löst ihn in Wasser und 20 Teilen 30 % iger Natron- lauge. Durch Zugabe dieser Lösung zur Tetrazoverbindung aus 1.9,1. Teilen 1-(4'- Arnino-benzoylamino)-4-amino-benzol wird in schwach lackmussaurer Lösung das Zwischen produkt hergestellt.
Dann versetzt man mit 8,4 Teilen 3-Methyl-5-pyrazolon in neutraler, wässriger Lösung und anschliessend mit 7,2 Teilen Natriumbicarbonat in 144 Teilen Was ser. Ist die Kupplung beendet, wird der Farb stoff heiss ausgesalzen, abfiltriert und ge trocknet.
Als dunkles Pulver löst sich der Farb stoff in Wasser und in konz. Schwefelsäure mit brauner Farbe. Er färbt Cellulosefasern in braunen Tönen an, die mit Kupfersulfat behandelt vor allem sehr gute Licht-, Wasch-, Säure- und Schweissechtheit zeigen.
<B> Additional patent </B> to main patent no. 282092. Process for the production of a copper-compatible tetrakisazo dye. \ Object. present patent is a method of making a copperable tetrakisazo dye. The process is characterized by the fact that one mole of
EMI0001.0006
and on the other hand combined with 1 mole of 3-methyl-5-pyrazolone.
1 -.) A nice tetrakisazo dye obtained is a dark powder and dissolves in water and conc. Sulfuric acid with a brown color.
<I> Example: </I> 17.2 parts of 1-arrrinobenzene-3-sulfonic acid are dianotated with 6.9 parts of sodium nitrite in a known manner and coupled in the presence of 14.6 parts of 30% strength sodium hydroxide solution and 25 parts of sodium carbonate with 16.0 parts of 1-acetylamino-2-oxy-benzene. When the coupling is ready, the dye is saponified by heating with dilute sodium hydroxide solution, with,
dilute sulfuric acid precipitated cold and filtered off. The dye is now dissolved in water and 17 parts of 30% strength sodium hydroxide solution, 20% sodium chloride is added and 7.7 parts of sodium nitrite and 50 parts of hydrochloric acid are added in the cold.
l, 16). The diazonium compound is filtered off and coupled in suspension with 11.0 parts of 1, 3-dioxy-benzene in the presence of 40 parts of sodium carbonate.
The disazo dye is acidified with 125 parts of the tetrazo compound of 1- (4'-amino-benzoyl-amino) -4-aminobenzene on the one hand with 1 mol of the disazo dye of the formula hydrochloric acid (d:
1.1.6), filtered and dissolved in water and 20 parts of 30% sodium hydroxide solution. By adding this solution to the tetrazo compound from 1.9.1. Parts of 1- (4'-amino-benzoylamino) -4-aminobenzene are used to prepare the intermediate product in weakly lacquer acidic solution.
8.4 parts of 3-methyl-5-pyrazolone in neutral, aqueous solution are then added, followed by 7.2 parts of sodium bicarbonate in 144 parts of water. Once the coupling has ended, the dye is salted out while hot, filtered off and dried.
As a dark powder, the dye dissolves in water and in conc. Sulfuric acid with a brown color. It dyes cellulose fibers in brown tones which, when treated with copper sulphate, show very good fastness to light, washing, acids and perspiration.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH282092T | 1949-11-25 | ||
| CH285002T | 1949-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH285002A true CH285002A (en) | 1952-08-15 |
Family
ID=25732149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH285002D CH285002A (en) | 1949-11-25 | 1949-11-25 | Process for the preparation of a copper-compatible tetrakisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH285002A (en) |
-
1949
- 1949-11-25 CH CH285002D patent/CH285002A/en unknown
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