CH218366A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH218366A CH218366A CH218366DA CH218366A CH 218366 A CH218366 A CH 218366A CH 218366D A CH218366D A CH 218366DA CH 218366 A CH218366 A CH 218366A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- wool
- amino
- preparation
- monoazo dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title 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 title description 3
- 239000000975 dye Substances 0.000 claims description 13
- 210000002268 wool Anatomy 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- 229920000297 Rayon Polymers 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper 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
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical class C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- -1 nitroazo Chemical group 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Es wurde gefunden, dass man einen neuen Monoazofarbstoff von sehr vorteilhaften fär- berischen Eigenschaften erhält, wenn man diazotiertes 1-Amin.o-2.-oxy-5-nitrobenzol in alkalischer Lösung mit 2-(N-4'-Oxy-ä'-carb- oxyphenyl) -amino- 5 -oxynaphthalin-7-sulfon- säure kuppelt und die Nitrogruppe reduziert.
Diese Reduktion der Nitrogruppe kann durch Behandeln des Nitroazofarbstoffes mit Lö sungen von Alkaldsulfiden oder -polysulfiden bewirkt werden.
Der neue Farbstoff färbt aus neutralen oder sauren Bädern Wolle bezw. synthe tische Fasern von animalischem Charakter, wie Superpolyamide oder Cellulasefasergut, besonders aber auch Mischungen von Cel.lu- losefasern und Wolle, zum Beispiel Viskose zellwolle und Wolle, in schwarzen Tönen. Hierbei erhält man auf beiden Faserarten leich stark g<I>a</I> ze Färbungen von gleichem Farb ton, während Acetatseideeffekte weiss gelas sen werden.
Die Echtheit der Färbungen wird wesentlich verbessert, wenn man sie mit Metallsalzen, insbesondere mit Salzen der Chromsäure und Salzen des dreiwertigen Chroms, .des Kupfers oder des Kobalts oder mit mehreren von diesen nachbehandelt. Der neue Farbstoff färbt Wolle und Zellwolle in schwarzen Tönen, deren Echtheit durch Nachbehandlung mit metallabgebenden Mitteln noch verbessert wird.
<I>Beispiel:</I> 46,2 Teile 1-Amino-2-oxy-5-nitrobenzol werden in üblicher Weise diazotiert, die Di- azolösung lässt man in eine Lösung von 112 Teilen 2-(N-4'-Oxy-3'-carboxyphenyl)-amino- 5-@oxynap.htha'lin-7-sulfonsäure in überschüs- sigerNatriumcabonatlösung einfliessen. Nach dem die Kupplung beendet ist, wird der Farbstoff ausgesalzen und abgesaugt.
Zur Reduktion des Farbstoffes echlämmt man die erhaltene Paste in viel Wasser auf, gibt Natronlauge bis zur schwach,alkalischen Re- aktion zu, erwärmt auf 50 , und versetzt dann mit einer Lösung von Na.triumsulfid in Wasser. Man rührt drei Stunden lang bei etwa 55 , stumpft durch Einleiten von Koh lendioxyd ab und salzt den Farbstoff aus, saugt ab und trocknet. Er zieht. gleichmässig auf Mischungen von Zellwolle (Viskosekunst- seide) und Wolle.
Bei der Nachbehandlung mit Natriumbichromat oder einer Mischung von Natriumbichromat- und. Chromifluorid- lösung, gegebenenfalls noch unter Zugabe von Kupfersulfat, erhält man sehr wasch echte, schwarze Färbungen. Im Gewebe allen falls vorhandene Acetatseide wird nicht an geschmutzt.
Process for the preparation of a monoazo dye. It has been found that a new monoazo dye with very advantageous coloring properties is obtained if diazotized 1-amin.o-2.-oxy-5-nitrobenzene in alkaline solution with 2- (N-4'-oxy-e '-carb-oxyphenyl) -amino-5-oxynaphthalene-7-sulfonic acid couples and reduces the nitro group.
This reduction of the nitro group can be effected by treating the nitroazo dye with solutions of alkali sulfides or polysulfides.
The new dye dyes wool or wool from neutral or acidic baths. Synthetic fibers of animal character, such as super polyamides or cellulase fibers, but especially mixtures of celeine-free fibers and wool, for example viscose cellulose and wool, in black tones. Here, on both types of fiber, you can easily get strong dyes of the same color, while acetate silk effects are left white.
The fastness of the dyeings is significantly improved if they are aftertreated with metal salts, in particular with salts of chromic acid and salts of trivalent chromium, copper or cobalt, or with several of these. The new dye dyes wool and rayon in black tones, the authenticity of which is further improved by post-treatment with metal-releasing agents.
<I> Example: </I> 46.2 parts of 1-amino-2-oxy-5-nitrobenzene are diazotized in the usual way, the diazole solution is left in a solution of 112 parts of 2- (N-4'- Pour oxy-3'-carboxyphenyl) -amino- 5-@oxynap.htha'lin-7-sulfonic acid into excess sodium carbonate solution. After the coupling has ended, the dye is salted out and filtered off with suction.
To reduce the dye, the paste obtained is slurried in a lot of water, sodium hydroxide solution is added until it has a weak, alkaline reaction, heated to 50, and then a solution of sodium sulfide in water is added. The mixture is stirred for three hours at about 55, blunted by passing in Koh lendioxyd and salted out the dye, filtered off with suction and dried. He pulls. evenly on mixtures of rayon (rayon artificial silk) and wool.
After treatment with sodium dichromate or a mixture of sodium dichromate and. Chromium fluoride solution, if necessary with the addition of copper sulfate, gives very washable, black colors. Any acetate silk in the fabric will not be soiled on.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE218366X | 1939-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH218366A true CH218366A (en) | 1941-12-15 |
Family
ID=5831258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH218366D CH218366A (en) | 1939-11-14 | 1940-10-09 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH218366A (en) |
-
1940
- 1940-10-09 CH CH218366D patent/CH218366A/en unknown
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