CH303904A - Process for the preparation of an acidic monoazo dye. - Google Patents
Process for the preparation of an acidic monoazo dye.Info
- Publication number
- CH303904A CH303904A CH303904DA CH303904A CH 303904 A CH303904 A CH 303904A CH 303904D A CH303904D A CH 303904DA CH 303904 A CH303904 A CH 303904A
- Authority
- CH
- Switzerland
- Prior art keywords
- monoazo dye
- acidic
- dye
- preparation
- mole
- Prior art date
Links
- 230000002378 acidificating effect Effects 0.000 title claims description 8
- 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 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- -1 methyl aminonaphthalene-6-sulfonic acid methylamide Chemical compound 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines sauren Monoazofarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines sauren Monoazofarbstoffes, welches darin besteht, dass inan ein Mol der Diazoverbindung aus 2 Amino - 4 - benzylsulfonyl - 4'-oxy--1,
1'-diphenyl- sulfon-3'-carbonsäure mit einem Mol 2-Methyl- ziniinonaplitlialin-6-sulfonsä.uremethylamid in dessen 1-Stelliing kuppelt.
Im nachfolgenden Beispiel bedeuten die Teile (lewiehtsteile und die Prozente Ge- wiehtsprozente.
<I>Beispiel:</I> 44,'l Teile 2-Ainino-4-benzylsulfonyl-4'-oxy- l.,l.'-diphenylsulfon-3'-carbonsäure werden in 500 Teilen Wasser mit Hilfe von Natrium- hy droxy d neutral gelöst.
Man versetzt die Lö- sung mit 36 Teilen 20%iger Natriumnitrit- lösung und lässt sie innerhalb von einer halben Stunde bei höchstens 10 zu einer Mischung %-on 40 Teilen konzentrierter Salzsäure und '300 Teilen Wasser einlaufen. Die gelbliche Diazoverbindung scheidet sich nahezu voll ständig aus. Nach beendigter Diazotierung wird die überschüssige salpetrige Säure zer stört.
Zu der Diazosuspension lässt man eine Lösung von 25 Teilen 2-Methylaminonaphtha- lin-6-siilfoiisäuremeth.ylamid in 200 Teilen Wasser und 15 Teilen konzentrierter Salzsäure bei l.0 zulaufen. Der sich sofort. bildende Monoazofarbstoff scheidet sich aas. Nach ein stündigem Rühren wird die Kupplungsmasse mit Natriumacetat kongoneutral gestellt.
Der Farbstoff wird abfiltriert und mit. Wasser ge waschen. Zur Umwandlung in das leicht lös- liehe Natriumsalz wird er in warmer Natrium- carbonatlösung gelöst. Man klärt die Lösung nötigenfalls von Verunreinigungen, salzt aus ihr den Farbstoff mittels Natriumchlorid aus, filtriert ihn ab und trocknet ihn.
Der neue saure Monoazofarbstoff ist ein rotes Pulver, löst sich in heissem Wasser mit roter Farbe und färbt Wolle aus neutralem oder schwach saurem Bad in leuchtend blau stichig roten Tönen, die sich beim Nachchro- mieren nur wenig ändern. Der Farbstoff eig net sich vorzüglich zum Färben nach dem Einbadchromierungsverfahren. Die Färbun gen sind sehr gut. licht-, walk- Lind carboni- sierecht.
Process for the preparation of an acidic monoazo dye. The subject of the present patent is a process for the preparation of an acidic monoazo dye, which consists in that inan one mole of the diazo compound from 2 amino - 4 - benzylsulfonyl - 4'-oxy - 1,
1'-diphenylsulfone-3'-carboxylic acid with one mole of 2-methylziniinonaplitlialin-6-sulfonsä.uremethylamid couples in its 1-Stelliing.
In the following example the parts (weight parts and the percentages mean weight percentages.
<I> Example: </I> 44, '1 part of 2-amino-4-benzylsulfonyl-4'-oxy- l., L .'-diphenylsulfone-3'-carboxylic acid are dissolved in 500 parts of water with the help of sodium hy droxy d dissolved neutrally.
The solution is mixed with 36 parts of 20% sodium nitrite solution and allowed to run in within half an hour at a maximum of 10 to a mixture of 40 parts of concentrated hydrochloric acid and 300 parts of water. The yellowish diazo compound is almost completely eliminated. When the diazotization is complete, the excess nitrous acid is destroyed.
A solution of 25 parts of 2-methylaminonaphthalin-6-siilfoiisäuremeth.ylamid in 200 parts of water and 15 parts of concentrated hydrochloric acid at 1.0 is allowed to run into the diazo suspension. The immediately. forming monoazo dye separates. After stirring for an hour, the coupling compound is rendered Congo neutral with sodium acetate.
The dye is filtered off and with. Wash water. To convert it into the easily soluble sodium salt, it is dissolved in warm sodium carbonate solution. If necessary, the solution is cleared of impurities, the dye is salted out using sodium chloride, filtered off and dried.
The new acidic monoazo dye is a red powder, dissolves in hot water with a red color and dyes wool from a neutral or weakly acidic bath in bright blue, pungent red shades that change only slightly when they are re-chromed. The dye is ideal for dyeing using the single-bath chromating process. The coloring is very good. light, walk and carbonization law.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH303904T | 1952-01-09 | ||
| CH301445T | 1952-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH303904A true CH303904A (en) | 1954-12-15 |
Family
ID=25734388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH303904D CH303904A (en) | 1952-01-09 | 1952-01-09 | Process for the preparation of an acidic monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH303904A (en) |
-
1952
- 1952-01-09 CH CH303904D patent/CH303904A/en unknown
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