CH311071A - 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
- CH311071A CH311071A CH311071DA CH311071A CH 311071 A CH311071 A CH 311071A CH 311071D A CH311071D A CH 311071DA CH 311071 A CH311071 A CH 311071A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- parts
- disazo dye
- dye
- methoxybenzene
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 13
- 239000000835 fiber Substances 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
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 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
- 239000004952 Polyamide Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process 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
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000728 polyester 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
- 239000012209 synthetic fiber Substances 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims 1
- 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
- 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 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
- 239000012535 impurity Substances 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 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
<B>Zusatzpatent</B> zum Hauptpatent Nr. 309184. Verfahren zur Herstellung eines wasserunlöslichen Disazofarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser unlöslichen Disazofarbstoffes, welches darin bestellt, dass man 1 Mol diazotiertes 1-Amino- 2-methoxybenzol in saurem Medium mit 1 Mol 1.-Amino-2-methoxy-5-methylbenzol kuppelt,
die erhaltene Aminomonoazoverbindung wei- terdiazotiert und mit 1 Mol 1-Oxy-3-methoxy- benzol kuppelt.
Der neue, wasserunlösliche Disazofarbstoff färbt, in üblicher Weise dispergiert, synthe tische Polyamidfasern in scharlachroten Tö nen von guten Licht-, Nass- und Sublimier- echtheitseigensehaften. Streifiges Nylon wird dabei gleichmässig gedeckt. Der neue Disazo- farbstoff kann bei erhöhter Temperatur auch zum Färben von Polyester- und Polyacryl nitrilfasern verwendet werden. Er eignet sich auch zum Färben von Lacken, Ölen Kunst harzen 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 kon zentrierter Salzsäure angerührt und nach Zu satz von 300 Teilen Eis mit einer Lösung von 35 Teilen Natriumnitrit in 100 Teilen Wasser versetzt. Hierauf wird die Temperatur der Diazolösung durch Zusatz von 350 Teilen Eis auf 0 gestellt und eine Lösung von 68,5 Tei len 1-Amino-2-methoxy-5-methylbenzol in 500 Teilen Wasser und 62 Teilen konzentrierter Salzsäure hinzugefügt.
Anschliessend stellt man die Reaktion der Masse mittels einer wäs serigen Lösung aus 130 Teilen Natriumacetat, kongoneutral und lässt die Masse einige Stun den rühren. Nun werden ihr 300 Teile Na- triumehlorid zugesetzt, worauf die gebildete Monoazoverbindung als Paste abfiltriert wird.
Hierauf wird diese in 1000 Teilen. Wasser und 160 Teilen konzentrierter Salzsäure an gerührt 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 Verunreinigun- gen und vereinigt sie mit einer Lösung aus 62 Teilen 1-Oxy-3-methoxybenzol, 500 Teilen Was ser,
55 Teilen 36o/oiger Natriumhydroxyd- lösung und 60 Teilen Natriumcarbonat. Der erhaltene neue Disazofarbstoff wird in übli cher Weise isoliert. Er färbt Nylon, Perlon und Dacron in scharlachroten Tönen von hervorragenden Echtheitseigenschaften.
<B> Additional patent </B> to main patent no. 309184. Process for the production of a water-insoluble disazo dye. The subject of the present patent is a process for the preparation of a water-insoluble disazo dye, which is ordered by coupling 1 mol of diazotized 1-amino-2-methoxybenzene in an acidic medium with 1 mol of 1-amino-2-methoxy-5-methylbenzene
the aminomonoazo compound obtained is further diazotized and coupled with 1 mol of 1-oxy-3-methoxybenzene.
The new, water-insoluble disazo dye, when dispersed in the usual manner, dyes synthetic polyamide fibers in scarlet red tones 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. It is also suitable for coloring paints, oils, synthetic resins or synthetic fibers in the mass.
In the example below, parts are parts by weight and percentages are percentages by weight.
Example: 61.5 parts of 1-amino-2-methoxybenzene who are stirred in 200 parts of water and 160 parts of concentrated hydrochloric acid and, after adding 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 68.5 parts of 1-amino-2-methoxy-5-methylbenzene in 500 parts of water and 62 parts of concentrated hydrochloric acid is added.
Then you set the reaction of the mass by means of a wäs serigen solution of 130 parts of sodium acetate, Congo-neutral and let the mass 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 divided into 1000 parts. Water and 160 parts of concentrated hydrochloric acid are stirred and, after 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 from minor impurities and combined with a solution of 62 parts of 1-oxy-3-methoxybenzene, 500 parts of water,
55 parts of 36% sodium hydroxide solution and 60 parts of sodium carbonate. The new disazo dye obtained is isolated in a customary manner. It dyes nylon, perlon and dacron in scarlet shades with excellent fastness properties.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311071T | 1952-11-07 | ||
| CH311072T | 1952-11-07 | ||
| CH309184T | 1955-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311071A true CH311071A (en) | 1955-11-15 |
Family
ID=27178323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311071D CH311071A (en) | 1952-11-07 | 1952-11-07 | Process for the preparation of a water-insoluble disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311071A (en) |
-
1952
- 1952-11-07 CH CH311071D patent/CH311071A/en unknown
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