CH218813A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH218813A CH218813A CH218813DA CH218813A CH 218813 A CH218813 A CH 218813A CH 218813D A CH218813D A CH 218813DA CH 218813 A CH218813 A CH 218813A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- dye
- preparation
- combined
- disazo dye
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 10
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 claims description 3
- 229910000906 Bronze Inorganic materials 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000010974 bronze Substances 0.000 claims description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 229910000029 sodium carbonate Inorganic materials 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
- 238000003756 stirring Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 214906. Verfahren zur Herstellung eines Disazofarbstoffes. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Herstellung eines Disazofarbstoffes, welches dadurch gekenn zeichnet ist, dass man die Diazoverbindung von 1-Amino-3-(co-sulfoacetylamino)-5-chlor- benzol mit 1-Amino-3-methylbenzol vereinigt,
den erhaltenen Monoazofarbstoff weiterdiazo- tiert und mit dem gemischten Harnstoff aus 2-Amino-5-oxynaphthahn-7-sulfonsäure und 1- Amino-4-acetylaminobenzol vereinigt.
<I>Beispiel:</I> 26,45 Gewichtsteile 1-Amino-3-(co-sulfo- acetylamino)-5-chlorbenzol werden in 150 Raumteilen Wasser und 50 Raumteilen 10 %- iger Natriumcarbonatlösung gelöst und mit 6,9 Gewichtsteilen Natriumnitrit versetzt. Hierauf wird das Gemisch bei 0-5 C unter Rühren langsam in überschüssige verdünnte Salzsäure eingetragen.
Die erhaltene Diazo- verbindung, die zum Teil ausgefallen ist, wird nun in schwach saurem Medium mit der be- rechneten Menge 1-Amino-3-methylbenzol ver einigt. Nach beendeter Kupplung wird der Monoazofarbstoff abgeschieden, aus verdünnter Sodalösung ungelöst und in Gegenwart von verdünnter Salzsäure auf übliche Weise in die Diazoverbindung übergeführt.
Diese wird nun in neutralem bis bicarbonatalkalischem Medium bei 0 o C unter Rühren mit einer wässrigen Lösung des Na-Salzes des gemischten Harn stoffes aus 2-Amino-5-oxynaphthalin-7-sulfon- säure und 1-Amino-4-acetylaminobenzol ver einigt. Nach beendeter Kupplung wird der Farbstoff abgetrennt und getrocknet.
Er bildet ein bronziges, glänzendes, dunkel braunes Pulver, das Baumwolle in blaustichig roten Tönen von sehr guten Nassechtheiten färbt.
<B> Additional patent </B> to main patent no. 214906. Process for the production of a disazo dye. The subject of the present additional patent is a process for the preparation of a disazo dye, which is characterized in that the diazo compound of 1-amino-3- (co-sulfoacetylamino) -5-chlorobenzene is combined with 1-amino-3-methylbenzene ,
the monoazo dye obtained is further diazo- tated and combined with the mixed urea of 2-amino-5-oxynaphthane-7-sulfonic acid and 1-amino-4-acetylaminobenzene.
<I> Example: </I> 26.45 parts by weight of 1-amino-3- (co-sulfo-acetylamino) -5-chlorobenzene are dissolved in 150 parts by volume of water and 50 parts by volume of 10% sodium carbonate solution and with 6.9 parts by weight Sodium nitrite added. The mixture is then slowly introduced into excess dilute hydrochloric acid at 0-5 ° C. with stirring.
The diazo compound obtained, which has partially precipitated, is now combined with the calculated amount of 1-amino-3-methylbenzene in a weakly acidic medium. After the coupling has ended, the monoazo dye is deposited, undissolved from dilute sodium carbonate solution and converted into the diazo compound in the usual manner in the presence of dilute hydrochloric acid.
This is now united in a neutral to bicarbonate-alkaline medium at 0 o C with stirring with an aqueous solution of the Na salt of the mixed urea from 2-amino-5-oxynaphthalene-7-sulfonic acid and 1-amino-4-acetylaminobenzene ver . After the coupling has ended, the dye is separated off and dried.
It forms a bronze, shiny, dark brown powder that dyes cotton in bluish red shades with very good wet fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE218813X | 1938-10-24 | ||
| CH214906T | 1939-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH218813A true CH218813A (en) | 1941-12-31 |
Family
ID=25725652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH218813D CH218813A (en) | 1938-10-24 | 1939-10-15 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH218813A (en) |
-
1939
- 1939-10-15 CH CH218813D patent/CH218813A/en unknown
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