CH309183A - 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
- CH309183A CH309183A CH309183DA CH309183A CH 309183 A CH309183 A CH 309183A CH 309183D A CH309183D A CH 309183DA CH 309183 A CH309183 A CH 309183A
- Authority
- CH
- Switzerland
- Prior art keywords
- disazo dye
- water
- parts
- mol
- dye
- 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 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 17
- 239000000835 fiber Substances 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 239000004677 Nylon Substances 0.000 claims description 3
- -1 aminomonoazo compound Chemical class 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
- 229920000728 polyester Polymers 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000004043 dyeing Methods 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
- 229920002239 polyacrylonitrile Polymers 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
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012209 synthetic fiber 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
Verfahren zur Herstellung eines wasserunlöslichen Disazofarbstoffes. Es wurde gefunden, da.ss man zu einem wertvollen neuen wasserunlöslichen Disazo- farbst.off.' gelangt, wenn man 1 Mol diazotier- tes 1.- Aniino-2-methoxybenzol in saurem Me dium mit 1.
Mol 1-Amino-2-methoxy-5-methyl- benzol kuppelt, die erhaltene Aminomonoazo- \,erbindung weiterdiazotiert und mit 1 Mol Oxi-benzol kuppelt.
Der neue wasserunlösliche Disazofarbstoff färbt, in üblicher Weise dispergiert, synthe tische Polyamidfasern in gelborangen Tönen von guten Licht-, Nass- und Sublimierecht- heitseigenschaften. Streifiges Nylon wird da bei gleichmässig gedeckt. Der neue Disazo- farbstoff kann bei erhöhter Temperatur auch zum. Färben von Polyester- und Polyaeryl- nitrilfasern verwendet werden.
Ausserdem zeichnet. er sich durch ein sehr gutes Ziehver mögen und grosse Farbtiefe auf Acetatreyon aus, wobei der Farbton jenem auf syntheti- sehen Polyamidfasern entspricht. Der neue, wasserunlösliche Disazofarbstoff eignet sich auch zum Färben von Lacken, Ölen, Kunst harzen oder von künstlichen Fasern in der Masse.
Im nachfolgenden Beispiel bedeuten die 'feile Gewiehtsteile. <I>Beispiel:</I> \?4,5 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 Salz säure hinzu und fügt zur Beschleunigung der Kupplung 45 Teile Natriumacetat zu. Wenn die Kupplung beendigt ist, versetzt man die Reaktionsmasse mit 200 Teilen Natrhun- eblorid und filtriert die ausgeschiedene Mono- azoverbindung ab.
Sie wird in 2000 Teilen Wasser und 64 Teilen konzentrierter Salzsäure angerührt, die Aufschlämmung durch Zusatz von Eis auf 10 bis 15 gestellt und mit einer Lösung von 15 Teilen Natriumnitrit in @50 Tei len Wasser diazotiert. Hierauf wird die Di- azolösung filtriert und das Filtrat mit einer Lösung von 20 Teilen Oxybenzol in 200 Tei len Wasser, 48 Teilen Natriumcarbonat,
21 Teilen 36prozentiger Natriumhydroxyd- lösung und 80 Teilen Natriumacetat bei 0 bis 5 vereinigt, wobei Kupplung zum Disazo- farbstoff eintritt. Dieser wird abfiltriert, neu tral gewaschen und getrocknet. Der neue, wasserunlösliche Disazofarbstoff ist ein braun rotes Pulver, das Acetatseide, Polyamidfasern,. wie Nylon und Perlon, und Polyesterfasern, wie zum Beispiel Dacron, in gelborangen Tö nen von hervorragenden Echtheitseigenschaf ten färbt.
Vergleichsweise sind der Farbstoff, wel cher als Anfangskomponente den Rest des Aminobenzols trägt, um 3@5 % und derjenige mit dem liest des 1-Amino-3-methylbenzols als Anfangskomponente um 55 % farbschwächer als der Farbstoff des Beispiels.
Process for the preparation of a water-insoluble disazo dye. It has been found that a valuable new water-insoluble disazo dye can be obtained. when 1 mol of diazotized 1.-aniino-2-methoxybenzene is obtained in acidic medium with 1.
Mol of 1-amino-2-methoxy-5-methylbenzene couples, the aminomonoazo compound obtained is further diazotized and coupled with 1 mole of oxybenzene.
The new water-insoluble disazo dye, when dispersed in the usual way, 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 at elevated temperature. Dyeing of polyester and polyaeryl nitrile fibers can be used.
Also draws. it is characterized by its very good drawability and great depth of color on Acetatreyon, the color tone corresponding to that on synthetic polyamide fibers. The new, water-insoluble disazo dye is also suitable for coloring paints, oils, synthetic resins or synthetic fibers in the mass.
In the following example the 'files mean weighted parts. <I> Example: </I> \? 4.5 parts of 1-amino-2-methoxybenzene are dissolved in 400 parts of water and 64 parts of concentrated hydrochloric acid and the solution is cooled to 0 by adding 400 parts of ice. 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 diazo mixture, and 45 parts of sodium acetate are added to accelerate the coupling. When the coupling has ended, 200 parts of sodium chloride are added to the reaction mass and the monoazo compound which has separated out is filtered off.
It is stirred into 2000 parts of water and 64 parts of concentrated hydrochloric acid, the slurry is adjusted to 10 to 15 by adding ice and diazotized with a solution of 15 parts of sodium nitrite in 50 parts of water. The diazole solution is then filtered and the filtrate is washed with a solution of 20 parts of oxybenzene in 200 parts of water, 48 parts of sodium carbonate,
21 parts of 36 percent sodium hydroxide solution and 80 parts of sodium acetate combined at 0 to 5, 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 that contains acetate silk, polyamide fibers. such as nylon and Perlon, and polyester fibers such as Dacron, dyes in yellow-orange tones with excellent fastness properties.
In comparison, the dye which carries the remainder of the aminobenzene as the initial component is 3 @ 5% and that with the 1-amino-3-methylbenzene read as the initial component is 55% weaker in color than the dye of the example.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH309183T | 1955-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH309183A true CH309183A (en) | 1955-08-31 |
Family
ID=4493749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH309183D CH309183A (en) | 1955-08-31 | 1952-10-31 | Process for the preparation of a water-insoluble disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH309183A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3100769A (en) * | 1959-12-15 | 1963-08-13 | Acna | Disazo dyes |
-
1952
- 1952-10-31 CH CH309183D patent/CH309183A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3100769A (en) * | 1959-12-15 | 1963-08-13 | Acna | Disazo dyes |
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