CH313100A - Process for the preparation of a water-insoluble monoazo dye - Google Patents
Process for the preparation of a water-insoluble monoazo dyeInfo
- Publication number
- CH313100A CH313100A CH313100DA CH313100A CH 313100 A CH313100 A CH 313100A CH 313100D A CH313100D A CH 313100DA CH 313100 A CH313100 A CH 313100A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- monoazo dye
- insoluble monoazo
- dye
- preparation
- 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 11
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- VPXKQSDRTTXXAG-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonyl fluoride Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(F)(=O)=O VPXKQSDRTTXXAG-UHFFFAOYSA-N 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- 229920003002 synthetic resin Polymers 0.000 claims description 3
- 239000000057 synthetic resin Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
-
- 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
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines wasserunlöslichen Monoazofarbstoffes Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser unlöslichen Monoazofarbstoffes, welches darin besteht, dass man 1 Mol diazotiertes 2-Amino- 5-nitrobenzol-l-sulfonsäurefluorid in saurem Medium mit 1 Mol 1-(N-Oxyäthyl-N-dioxäthyl- amino)-3-methylbenzol kuppelt.
Der neue, wasserunlösliche Monoazofarb- stoff stellt ein violettes Pulver dar, welches aus Äthanol umkristallisiert bei 204 bis 206 schmilzt. In üblicher Weise dispergiert, färbt der Farbstoff Acetatreyon in violetten Tönen, welche hervorragend lichtecht und rein weiss ätzbar sind.
Seine 'Färbungen auf syntheti- schen Polyamidfasern sind etwas gelbstichiger. Der neue, wasserunlösliche Monoazofarbstoff eignet sich auch zum Färben von Lacken, Ölen, Kunstharzen oder von künstlichen Fa sern in der Masse.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile, und die Prozente sind in Gewichtsprozenten angegeben.
<I>Beispiel</I> 7,6 Teile Natriumnitrit werden innerhalb einer Stunde bei @60 ' in 90 Teile konzentrierte Schwefelsäure eingetragen. Die erhaltene Lö sung wird auf 10 gekühlt, bei dieser Tem peratur mit 100 Teilen konzentrierter Essig säure und hernach mit. 22 'Teilen 2-Amino- 5 - nitrobenzol -1- sulfonsäurefluor id versetzt, worauf man erneut 100 Teile konzentrierte Essigsäure zufügt.
Nach einer'Stunde stumpft man den Nitritüberschuss der Diazotierungs- masse mit 5 Teilen Harnstoff ab und bringt sie anschliessend auf <B>250</B> Teile Eis.
Hierauf vereinigt man die Diazotierungsmasse mit einer vorbereiteten Lösung von 29,5 Teilen 1- (N-Oxyäthyl - N - dioxäthylamino) -3-methyl- benzol, 50 Teilen Wasser, 20 Teilen 30prozen- tiger Salzsäure und 50 Teilen Eis. Der neue Monoazofarbstoff beginnt alsbald auszufallen. Sobald dessen Abscheidung beendet ist, wird er durch Abfiltrieren isoliert, mit Wasser säurefrei gewaschen und hernach getrocknet.
Der neue, wasserunlösliche Monoazofarb- stoff stellt ein violettes Pulver dar, welches aus Äthanol umkristallisiert bei 204 bis 206 schmilzt. In üblicher Weise dispergiert, färbt der Farbstoff Acetatreyon in violetten Tönen, welche hervorragend lichtecht und rein weiss ätzbar sind.
Seine !Färbungen auf syntheti schen :Polyamidfasern sind etwas gelbstiehi- ger. Der neue, wasserunlösliche Monoazofarb- stoff eignet, sich auch zum Färben von Lacken, Ölen, Kunstharzen oder von künstlichen Fa sern in der Masse.
Process for the preparation of a water-insoluble monoazo dye The present patent relates to a process for the preparation of a water-insoluble monoazo dye, which consists in adding 1 mol of diazotized 2-amino-5-nitrobenzene-1-sulfonic acid fluoride in an acidic medium with 1 mol of 1- (N -Oxyäthyl-N-dioxäthyl- amino) -3-methylbenzene couples.
The new, water-insoluble monoazo dye is a violet powder which, recrystallized from ethanol, melts at 204 to 206. Dispersed in the usual way, the dye Acetatreyon dyes in violet shades, which are extremely lightfast and can be etched in pure white.
His' dyeings on synthetic polyamide fibers are somewhat more yellowish. The new, water-insoluble monoazo dye is also suitable for coloring paints, oils, synthetic resins or artificial fibers in bulk.
In the example below, parts are parts by weight and percentages are percentages by weight.
<I> Example </I> 7.6 parts of sodium nitrite are introduced into 90 parts of concentrated sulfuric acid at @ 60 'within one hour. The solution obtained is cooled to 10, at this temperature with 100 parts of concentrated acetic acid and then with. 22 parts of 2-amino-5-nitrobenzene-1-sulfonic acid fluoride are added, whereupon 100 parts of concentrated acetic acid are again added.
After one hour, the excess nitrite of the diazotization mass is blunted with 5 parts of urea and then brought to 250 parts of ice.
The diazotization mass is then combined with a prepared solution of 29.5 parts of 1- (N-oxyethyl-N-dioxäthylamino) -3-methylbenzene, 50 parts of water, 20 parts of 30 percent hydrochloric acid and 50 parts of ice. The new monoazo dye soon begins to precipitate. As soon as its separation has ended, it is isolated by filtering off, washed acid-free with water and then dried.
The new, water-insoluble monoazo dye is a violet powder which, recrystallized from ethanol, melts at 204 to 206. Dispersed in the usual way, the dye Acetatreyon dyes in violet shades, which are extremely lightfast and can be etched in pure white.
Its! Dyeings on synthetic: polyamide fibers are a little more yellowish. The new, water-insoluble monoazo dye is also suitable for coloring paints, oils, synthetic resins or artificial fibers in bulk.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH313100T | 1952-12-24 | ||
| CH312188T | 1952-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH313100A true CH313100A (en) | 1956-03-15 |
Family
ID=25735879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH313100D CH313100A (en) | 1952-12-24 | 1952-12-24 | Process for the preparation of a water-insoluble monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH313100A (en) |
-
1952
- 1952-12-24 CH CH313100D patent/CH313100A/en unknown
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