CH285000A - 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
- CH285000A CH285000A CH285000DA CH285000A CH 285000 A CH285000 A CH 285000A CH 285000D A CH285000D A CH 285000DA CH 285000 A CH285000 A CH 285000A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- dye
- copper
- preparation
- compatible
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation 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
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-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
- 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 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 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
- 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
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 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
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 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 Tetrakisazofarbatoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines kupferbaren Tetrakieazofarbstoffes. Das Verfahren ist. da durch gekennzeichnet, dass man 1 Mol der
EMI0001.0004
i und anderseits mit 1 Mol 3-Methyl-5-pyrazolon vereinigt.
Der erhaltene neue Tetrakisazofarbstoff stellt ein dunkles Pulver dar und löst sich in Wasser und konz. Schwefelsäure mit brauner Farbe.
<I>Beispiel:</I> Man diazotiert 20,75 Teile I - Amino-4- chlor-benzol-3-sulfonsäure mit 6,9 Teilen Na- triurnnitrit in bekannter Weise und kuppelt in Anwesenheit von 14,6 Teilen 30%iger Na- tronlauge und 25 Teilen Natriumcarbonat mit 16,0 Teilen 1-Acetylamino-2-oxy-benzol. Ist, die Kupplung fertig,
wird der Farbstoff durch Erhitzen mit verdünnter Natronlauge verseift, mit verdünnter Schwefelsäure kalt ausgefällt und abfiltriert. Man löst nun den Farbstoff in Wasser und 17 Teilen 30%iger Natron- lauge, versetzt mit 20% Kochsalz und diazo- tiert in der Kälte mit 7,
7 Teilen Natriumnitrit und 50 Teilen Salzsäure<B>(d:</B> 1,16). Die Diazo- niumverbindung wird abfiltriert und in An- schlämmung mit 11,0 Teilen 1,3-Dioxy-benzol in Gegenwart von 40 Teilen Natriumcarbonat gekuppelt.
Den Disazofarbstoff säuert man Tetrazoverbindung von 1-(4'-Amino-benzoyl- amino)-4-amino-benzol einerseits mit 1 Mol des Disazofarbstoffes der Formel mit 125 Teilen Salzsäure<B>(d:
</B> 1,16) aus, fil triert und löst ihn in Wasser und 20 Teilen 30 % iger Natronlauge. Durch Zugabe dieser Lösung zur Tetrazoverbindung aus 1.9,1 Teilen 1.- (4'-Amino-benzoylamino) -4-amino-'benzol wird in schwach lackmussaurer Lösung das Zwischenprodukt 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 Tei len Wasser. Ist die -Kupplung beendet, wird der Farbstoff heiss ausgesalzen, abfiltriert und getrocknet.
.Als dunkles Pulver löst sich der Farbstoff in Wasser und in konz. Schwefelsäure mit brauner Farbe. Er färbt. Cellulosefasern in braunen Tönen an, die mit Kupfersulfat be handelt vor allem sehr gute Licht-, Wasch-, Säure- und Schweissechtheit zeigen.
<B> Additional patent </B> to the main patent. No. 282092. Process for the preparation of a copper-compatible tetrakisazo carbate. The subject of the present patent is a process for the preparation of a copper-compatible tetrakeazo dye. The procedure is. characterized in that one mole of the
EMI0001.0004
i and on the other hand combined with 1 mol of 3-methyl-5-pyrazolone.
The new tetrakisazo dye obtained is a dark powder and dissolves in water and conc. Sulfuric acid with a brown color.
<I> Example: </I> 20.75 parts of I-amino-4-chloro-benzene-3-sulfonic acid are diazotized with 6.9 parts of sodium nitrite in a known manner and coupled in the presence of 14.6 parts of 30% iger sodium hydroxide solution and 25 parts of sodium carbonate with 16.0 parts of 1-acetylamino-2-oxy-benzene. Is the clutch ready
the dye is saponified by heating with dilute sodium hydroxide solution, precipitated cold with dilute sulfuric acid and filtered off. The dye is now dissolved in water and 17 parts of 30% sodium hydroxide solution, mixed with 20% sodium chloride and diazotized in the cold with 7,
7 parts of sodium nitrite and 50 parts of hydrochloric acid (d: 1.16). 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 tetrazo compound of 1- (4'-amino-benzoyl-amino) -4-amino-benzene on the one hand with 1 mol of the disazo dye of the formula with 125 parts of hydrochloric acid <B> (d:
</B> 1.16), filters and dissolves it in water and 20 parts of 30% sodium hydroxide solution. By adding this solution to the tetrazo compound of 1.9.1 parts of 1.- (4'-amino-benzoylamino) -4-amino-'benzene, the intermediate product is prepared in a weakly lacquer acidic solution. Then moved.
one with 8.4 parts of 3-methyl-5-pyrazolone in neutral, aqueous solution and then with 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. He colors. Cellulose fibers in brown tones, which are treated with copper sulfate and especially 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 | ||
| CH285000T | 1949-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH285000A true CH285000A (en) | 1952-08-15 |
Family
ID=25732147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH285000D CH285000A (en) | 1949-11-25 | 1949-11-25 | Process for the preparation of a copper-compatible tetrakisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH285000A (en) |
-
1949
- 1949-11-25 CH CH285000D patent/CH285000A/en unknown
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