CH308405A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH308405A CH308405A CH308405DA CH308405A CH 308405 A CH308405 A CH 308405A CH 308405D A CH308405D A CH 308405DA CH 308405 A CH308405 A CH 308405A
- Authority
- CH
- Switzerland
- Prior art keywords
- monoazo dye
- group
- preparation
- amino
- dye
- Prior art date
Links
- 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 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- ZIQWUYNDHGXLIN-UHFFFAOYSA-N 4-amino-5-(4-methylphenyl)sulfonyloxynaphthalene-2,7-disulfonic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC(N)=C12 ZIQWUYNDHGXLIN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- NGWKGSCSHDHHAJ-YPFQVHCOSA-N Liquoric acid Chemical compound C1C[C@H](O)C(C)(C)C2CC[C@@]3(C)[C@]4(C)C[C@H]5O[C@@H]([C@](C6)(C)C(O)=O)C[C@@]5(C)[C@@H]6C4=CC(=O)C3[C@]21C NGWKGSCSHDHHAJ-YPFQVHCOSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000203 mixture 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
- 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
- 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
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. lTegensta.nd vorliegenden Patentes ist ein Verfahren zur Herstellung eines Monoazo- farbstoffes. Das Verfahren ist dadurch ge kennzeichnet, dass man 1-Amino-8-acyjoxy- riaphtlialin-3,6-disulfonsäure dia.zotiert, mit Dibenzylanilin kuppelt und hierauf die Aeylogruppe zur Hydroxylgruppe verseift.
Der erhaltene neue Monoazofarbstoff stellt. ein hellrotes Pulver dar, das Wolle aus neu tralem bis schwach saurem Färbebad in sehr klaren, < gleichmässigen Rottönen färbt.
Beispiel: 1.11,9 Teile 1-Amino-8-tosyloxy-naphthalin- 3,6-disulfonsäure werden in 600 Teilen hei ssem Wasser als Natriumsalz gelöst;
die Lö- sun- wird abgekühlt, bei 20 mit 60 Teilen Salzsäure konz. versetzt und bei 6 mit einer Lösung von 20,7 Teilen Natriumnitrit in 4'' Teilen Wasser rasch diazotiert. Die Diazo- suspension wird bei 30 bis 32 in eine heiss licro-estellte Lösung von 81,9 Teilen Dibenzyl- aniliii in 750 Teilen Äthanol einfliessen gelas sen.
Dann versetzt man mit 171 Volumteilen einer 40 o/oigen Natriuma.eetatlösung und rührt bei schwach kongosaurer Reaktion 8 bis 10 Stunden bei 30 bis zum Verschwinden der Diazoverbindung. Dann wird aufgeheizt, der Alkohol a.bdestilliert, die Farbstofflösung mit Natriumearbonat neutralisiert und mit so viel Ätznatron versetzt, dass eine 4 o/oige Natron- lauge entsteht.
Nach einstündigem Rühren bei 80 bis 85 ist die Verseif'ung der Tosyl- oxy- zur Hydroxylgruppe beendet. Man neu tralisiert mit Salzsäure, salzt aus, kühlt ab, filtriert den als rotes Kristallpulver ausge schiedenen Farbstoff ab und trocknet ihn.
Der Farbstoff stellt ein hellrotes Pulver vor, das sich in Wasser mit roter Farbe gut löst. Wolle wird aus neutralem bis schwach saurem Färbebad in sehr klaren, gleichmässi gen Rottönen gefärbt. Die Wollfärbungen sind sehr gut na.ss- und lichtecht.
Process for the preparation of a monoazo dye. The present patent is a process for the preparation of a monoazo dye. The process is characterized in that 1-amino-8-acyjoxy-riaphtlialin-3,6-disulfonic acid is dia.zotiert, coupled with dibenzylaniline and then saponified the aeylo group to the hydroxyl group.
The new monoazo dye obtained represents. a light red powder that dyes wool from neutral to weakly acidic dye baths in very clear, even red tones.
Example: 1.11.9 parts of 1-amino-8-tosyloxy-naphthalene-3,6-disulfonic acid are dissolved as the sodium salt in 600 parts of hot water;
the solution is cooled, concentrated at 20 with 60 parts of hydrochloric acid. added and rapidly diazotized at 6 with a solution of 20.7 parts of sodium nitrite in 4 ″ parts of water. At 30 to 32, the diazo suspension is poured into a hot licoric acid solution of 81.9 parts of dibenzyl aniliii in 750 parts of ethanol.
171 parts by volume of a 40% sodium acetate solution are then added and the mixture is stirred in a weakly Congo acidic reaction for 8 to 10 hours at 30 until the diazo compound disappears. Then it is heated up, the alcohol is distilled off, the dye solution is neutralized with sodium carbonate and so much caustic soda is added that a 4% sodium hydroxide solution is formed.
After stirring for one hour at 80 to 85, the hydrolysis of the tosyloxy group is complete. It is neutralized with hydrochloric acid, salted out, cooled, filtered off the dyestuff separated out as red crystal powder and dried.
The dye represents a light red powder that dissolves well in water with a red color. Wool is dyed from a neutral to slightly acidic dye bath in very clear, uniform shades of red. The wool dyeings are very good waterproof and lightfast.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308405T | 1952-02-05 | ||
| CH304042T | 1952-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308405A true CH308405A (en) | 1955-07-15 |
Family
ID=25734735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308405D CH308405A (en) | 1952-02-05 | 1952-02-05 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308405A (en) |
-
1952
- 1952-02-05 CH CH308405D patent/CH308405A/en unknown
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