CH311065A - 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
- CH311065A CH311065A CH311065DA CH311065A CH 311065 A CH311065 A CH 311065A CH 311065D A CH311065D A CH 311065DA CH 311065 A CH311065 A CH 311065A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- disazo dye
- mol
- parts
- fibers
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 13
- 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 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 239000004677 Nylon Substances 0.000 claims description 3
- -1 aminomonoazo compound Chemical class 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229920001778 nylon Polymers 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 239000003973 paint Substances 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
- 238000004040 coloring Methods 0.000 claims 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- 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
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate 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
- 238000003756 stirring Methods 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
Zusatzpatent zum Hauptpatent Nr. 309184. <B>Verfahren zur</B> 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-methoxybenzol in saurem Medium mit 1.
Mol 1-Amino-2,5-dimethoxybenzol kuppelt, die er haltene Aminomonoazoverbindung weiter diazotiert und mit einem Gemisch von 1/2 Mol Oxybenzol und 1/2 Mol 1.-Oxy-3-methoxyben- zol kuppelt.
Der neue, wasserunlösliche Disazofarbstoff färbt, in üblicher Weise dispergiert, synthe tische Polyamidfasern in reinen roten Tönen von guten Licht-, Nass- und Sublimierecht- heitseigenschaften. Streifiges Nylon wird da bei gleichmässig gedeckt. Der neue Disazofarb- stoff kann bei erhöhter Temperatur auch zum Färben von Polyester- und Polyacrylnitril- fasern verwendet: werden.
Ausserdem zeichnet er sich durch ein sehr gutes Ziehvermögen und grosse Farbtiefe auf Acetatseide aus, wo bei der Farbton jenem auf synthetischen Poly- amidfasern entspricht. Der neue, wasserunlös liche Disazofarbstoff eignet sich auch zum Färben von Lacken, Ölen, Kunstharzen oder von künstlichen Fasern in der Masse.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile, und die Prozente sind in Gewichtsprozenten angegeben.
Beispiel: 61.,5 Teile 1-Amino-2-methoxybenzol wer den in 200 Teilen Wasser und 160 Teilen konzentrierter Salzsäure angerührt und nach Zusatz von 300 Teilen Eis mit einer Lösung von 35 Teilen Natriumnitrit in 100 Teilen Wasser versetzt. Hierauf wird die Tempera tur der Diazolösung durch Zusatz von 350 Teilen Eis auf 0 gestellt und eine Lösung von 76,5 Teilen 1-Amino-2,5-dimethoxybenzol in 500 Teilen Wasser und 62 Teilen konzen trierter Salzsäure hinzugefügt. Anschliessend stellt man die Reaktion der Masse mittels einer wässerigen Lösung aus 130 Teilen Na triumacetat kongoneutral und lässt die Masse einige Stunden rühren.
Nun werden ihr 300 Teile Natriumchlorid zugesetzt, worauf die gebildete Monoazoverbindung als Paste abfil- t.riert wird. Hierauf wird diese in 1000 Teilen Wasser und 160 Teilen konzentrierter Salz säure angerührt und nach Zusatz von 200 Teilen Eis mit einer Lösung von 35 Teilen Natriumnitrit in 100 Teilen Wasser diazotiert. Man filtriert die Diazolösung von geringen Verunreinigungen und vereinigt sie mit einer Lösung aus 23,5 Teilen Oxybenzol, 31.
Teilen 1.-Oxy-3-methoxyberrzol, 500 Teilen Wasser, 55 Teilen 36o/oiger Natriumhy droxydlösung und 60 Teilen Natriumcarbonat. Das erhal tene Gemisch von Disazofarbstoffen wird in üblicher Weise isoliert. Es färbt Acetatseide, Nylon, Perlon und Dacron in reinen roten Tönen von hervorragenden Echtheitseigen schaften.
Additional patent to main patent no. 309184. <B> Process for </B> 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 mixing 1 mol of diazotized 1-amino-2-methoxybenzene in an acidic medium with 1.
Molecules of 1-amino-2,5-dimethoxybenzene, the aminomonoazo compound he obtained is further diazotized and coupled with a mixture of 1/2 mol of oxybenzene and 1/2 mol of 1.-oxy-3-methoxybenzene.
The new, water-insoluble disazo dye, when dispersed in the usual way, dyes synthetic polyamide fibers in pure red shades with good light, wet and sublimation fastness properties. Striped nylon is evenly covered. The new disazo dye can also be used for dyeing polyester and polyacrylonitrile fibers at higher temperatures.
It is also characterized by very good drawability and great depth of color on acetate silk, where the color tone corresponds to that on synthetic polyamide fibers. The new, water-insoluble disazo dye is also suitable for dyeing paints, oils, synthetic resins or artificial fibers in bulk.
In the example below, parts are parts by weight and percentages are percentages by weight.
Example: 61st, 5 parts of 1-amino-2-methoxybenzene are stirred in 200 parts of water and 160 parts of concentrated hydrochloric acid and, after 300 parts of ice, a solution of 35 parts of sodium nitrite in 100 parts of water is added. The temperature of the diazo solution is then set to 0 by adding 350 parts of ice and a solution of 76.5 parts of 1-amino-2,5-dimethoxybenzene in 500 parts of water and 62 parts of concentrated hydrochloric acid is added. The reaction of the mass is then made congoneutral by means of an aqueous solution of 130 parts of sodium acetate and the mass is left to stir for a few hours.
300 parts of sodium chloride are then added to it, whereupon the monoazo compound formed is filtered off as a paste. This is then stirred in 1000 parts of water and 160 parts of concentrated hydrochloric acid and, after the addition of 200 parts of ice, diazotized with a solution of 35 parts of sodium nitrite in 100 parts of water. The diazo solution is filtered to remove minor impurities and combined with a solution of 23.5 parts of oxybenzene, 31.
Parts of 1.-oxy-3-methoxyberrzene, 500 parts of water, 55 parts of 36% sodium hydroxide solution and 60 parts of sodium carbonate. The obtained mixture of disazo dyes is isolated in the usual way. It dyes acetate silk, nylon, perlon and dacron in pure red shades with excellent fastness properties.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311072T | 1952-11-07 | ||
| CH311065T | 1952-11-07 | ||
| CH309184T | 1955-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311065A true CH311065A (en) | 1955-11-15 |
Family
ID=27178317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311065D CH311065A (en) | 1952-11-07 | 1952-11-07 | Process for the preparation of a water-insoluble disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311065A (en) |
-
1952
- 1952-11-07 CH CH311065D patent/CH311065A/en unknown
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