CH311059A - Process for the preparation of a water-insoluble disazo dye. - Google Patents
Process for the preparation of a water-insoluble disazo dye.Info
- Publication number
- CH311059A CH311059A CH311059DA CH311059A CH 311059 A CH311059 A CH 311059A CH 311059D A CH311059D A CH 311059DA CH 311059 A CH311059 A CH 311059A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- disazo dye
- parts
- new
- fibers
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 12
- 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 14
- 239000000835 fiber Substances 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims description 4
- 239000004677 Nylon Substances 0.000 claims description 3
- -1 aminomonoazo compound Chemical class 0.000 claims description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
- 229920001778 nylon Polymers 0.000 claims description 3
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 238000000859 sublimation Methods 0.000 claims description 2
- 230000008022 sublimation Effects 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229920004934 Dacron® Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000706 filtrate 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
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 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
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 309183, Verfahren zur Herstellung eines wasserunlöslichen Disazofarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser unlöslichen Disazofarbstoffes, welches darin besteht, dass man 1 Mol diazotiertes 1-Amino- 2-methoxvbenzol in saurem Medium mit 1 Mol 1-Amino-2-methoxy-5-methylbenzol kuppelt,
die erhaltene Aminomonoazoverbindung wei- terdiazotiert und mit 1 hIol 1-Oxy-2-methoxy- benzol kuppelt.
Der neue, wasserunlöslielie Disazofarbstoff färbt, in üblicher Weise dispergiert, synthe tische Polyamidfasern in gelborangen Tönen von guten Licht-, Nass- und Sublimierecht- heitseigensehaften. Streifiges Nylon wird da bei gleichmässig gedeckt. Der neue Disazofarb- stoffkann bei erhöhter Temperatur auch zum Färben von Polyester- und Polya.crylnitril- fasern verwendet werden.
Ausserdem zeichnet er sieh durch ein sehr gutes Ziehvermögen und grosse Farbtiefe auf Acetatreyon aus, wo bei der Farbton jenem auf synthetischen Poly- amidfasern entsprielit. Auch zum Färben von Lacken, Ölen, Kunstharzen oder von künst lichen Fasern in der Masse eignet sich der neue Disazofarbstoff.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile, und die Prozente sind in Gewichtsprozenten angegeben.
Beispiel: 24,5 Teile 1-Amino-2-methoxybenzol wer den in 400 Teilen Wasser und 64 Teilen kon zentrierter Salzsäure gelöst und die Lösung durch Zusatz von 400 Teilen. Eis auf 0 ab gekühlt. Hierauf diazotiert man das 1-Amino- 2-methoxybenzol mit einer Lösung von 14 Tei len Natriumnitrit in 40 Teilen Wasser.
Nach beendigter Diazotierung tropft man zum Di- azogemisch eine Lösung von 27 Teilen 1- Amino-2-methoxy-5-methylbenzol in 500 Tei len Wasser und 32 Teilen konzentrierter Salzsäure hinzu und fügt zur Beschleunigung der Kupplung 45 Teile Natriumacetat zu. Wenn die Kupplung beendet ist, versetzt man die Reaktionsmasse mit 200 Teilen Natrium chlorid und filtriert die ausgeschiedene Mono azoverbindung ab.
Sie wird in 2000 Teilen )Vasser und 64 Teilen konzentrierter Salz säure angerührt, die Aufschlämmung durch Zusatz von Eis auf 1.0--15 gestellt und mit einer Lösung von 15 Teilen Natriumnitrit in 50 Teilen Wasser diazotiert. Hierauf wird die Diazolösung filtriert und das Filtrat mit einer Lösung von 26 Teilen 1-Oxy-2-methoxy- benzol in 200 Teilen Wasser, 48 Teilen Na- triumea.rbonat, 21 Teilen 36 /oiger Natrium hydroxydlösung und 80 Teilen Natriumacetat bei 0-5 vereinigt,
wobei Kupplung zum Disazofarbstoff eintritt. Dieser wird abfil- triert, neutral gewaschen und getrocknet. Der neue, wasserunlösliche Disazofarbstoff ist ein braunrotes Pulver, welches Acetatseide, Poly- amidfasern, wie z. B. Nylon und Perlon , und Polyesterfasern, wie z. B. Dacron , in gelborangen Tönen von hervorragenden Echt heitseigenschaften färbt.
<B> Additional patent </B> to main patent no. 309183, process for the production of a water-insoluble disazo dye. The present patent relates to a process for the preparation of a water-insoluble disazo dye, which consists in coupling 1 mol of diazotized 1-amino-2-methoxybenzene with 1 mol of 1-amino-2-methoxy-5-methylbenzene in an acidic medium,
the aminomonoazo compound obtained is further diazotized and coupled with 1 hIol of 1-oxy-2-methoxybenzene.
The new, water-insoluble disazo dye, when dispersed in the usual manner, dyes synthetic polyamide fibers in yellow-orange shades with good light, wet and sublimation fastness properties. Striped nylon is evenly covered. The new disazo dye can also be used to dye polyester and polyacrylonitrile fibers at elevated temperatures.
In addition, it is characterized by very good drawability and great depth of color on Acetatreyon, where the color tone corresponds to that on synthetic polyamide fibers. The new disazo dye is also suitable for coloring paints, oils, synthetic resins or artificial fibers in the mass.
In the example below, parts are parts by weight and percentages are percentages by weight.
Example: 24.5 parts of 1-amino-2-methoxybenzene who dissolved in 400 parts of water and 64 parts of concentrated hydrochloric acid and the solution by adding 400 parts. Ice cooled to 0. The 1-amino-2-methoxybenzene is then diazotized with a solution of 14 parts of sodium nitrite in 40 parts of water.
When the diazotization is complete, a solution of 27 parts of 1-amino-2-methoxy-5-methylbenzene in 500 parts of water and 32 parts of concentrated hydrochloric acid is added dropwise to the diazotization mixture, and 45 parts of sodium acetate are added to accelerate the coupling. When the coupling is complete, 200 parts of sodium chloride are added to the reaction mass and the precipitated monoazo compound is filtered off.
It is stirred up in 2000 parts of water and 64 parts of concentrated hydrochloric acid, the suspension is adjusted to 1.0-15 by adding ice and diazotized with a solution of 15 parts of sodium nitrite in 50 parts of water. The diazo solution is then filtered and the filtrate is washed with a solution of 26 parts of 1-oxy-2-methoxybenzene in 200 parts of water, 48 parts of sodium carbonate, 21 parts of 36% sodium hydroxide solution and 80 parts of sodium acetate at 0- 5 united,
coupling to the disazo dye occurs. This is filtered off, washed neutral and dried. The new, water-insoluble disazo dye is a brown-red powder which contains acetate silk, polyamide fibers, such as B. nylon and Perlon, and polyester fibers such. B. Dacron, in yellow-orange tones of excellent authenticity properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311059T | 1952-10-31 | ||
| CH309183T | 1955-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311059A true CH311059A (en) | 1955-11-15 |
Family
ID=25735593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311059D CH311059A (en) | 1952-10-31 | 1952-10-31 | Process for the preparation of a water-insoluble disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311059A (en) |
-
1952
- 1952-10-31 CH CH311059D patent/CH311059A/en unknown
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