CH328656A - Process for the preparation of chromium-containing monoazo dyes - Google Patents
Process for the preparation of chromium-containing monoazo dyesInfo
- Publication number
- CH328656A CH328656A CH328656DA CH328656A CH 328656 A CH328656 A CH 328656A CH 328656D A CH328656D A CH 328656DA CH 328656 A CH328656 A CH 328656A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- chromium
- dyes
- monoazo dyes
- preparation
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 16
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 12
- 229910052804 chromium Inorganic materials 0.000 title claims description 12
- 239000011651 chromium Substances 0.000 title claims description 11
- 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 claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 230000007935 neutral effect Effects 0.000 claims description 6
- 239000000987 azo dye Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-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
- 239000002253 acid Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 241000283153 Cetacea Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 229910004727 OSO3H Inorganic materials 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- NHIRTPYVBADBSR-UHFFFAOYSA-J [Na+].[Cr+3].Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O Chemical compound [Na+].[Cr+3].Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O NHIRTPYVBADBSR-UHFFFAOYSA-J 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- -1 amino compound Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von ehromhaltigen Monoazofarbstoffen Es wurde gefunden, dass man wertvolle neue chromhaltige Monoazofarbstoffe erhält, wenn man kernsulfonsäuregruppenfreie o- Oxy- o' - carboxy - azofarbstoffe, welche die Gruppe =S02 CH2 CH2-OIS03H ein- oder zweimal enthalten,
durch Behandeln mit Chromkomplexverbindungen von aroma tischen o-Oxycarbonsäuren (deutsche Patent schrift Nr.741462), insbesondere Ohromsalicyl- säure oder ihren Salzen, in neutralem oder alkalischem Medium in ihre komplexen Chrom verbindungen überführt. In den fertigen chromhaltigen Farbstoffen beträgt das Ver hältnis von Farbstoffmolekül zu Chromatom 2: 1 bis 1:1, vorzugsweise 2: 1.
Die bei dem vorliegenden Verfahren zur Anwendung kommenden Ausgangsfarbstoffe können in der Weise erhalten werden, dass man in o-Oxy-o'-carboxy-azofarbstoffe, die keine Kernsulfonsäuregruppen enthalten, die Gruppe -.S02-CH2 CH2-0!SO3H ein- oder zweimal einführt.
Die Herstellung der Diazo- und Azokom- ponenten kann nach üblichen Verfahren er folgen, indem man eine diazotierbare Amino- verbindung oder eine Azokomponente mit der Gruppe =S02 CH2 CH2 OH mit starker Schwefelsäure umsetzt, wobei saure Schwefelsäureester entstehen. Durch Diazo- tieren und:
anschliessende Kupplung kann dann der Farbstoff mit der Gruppe -S02 CHF CHe- OSO3H gebildet werden. Man kann aber auch Azo- farbstoffe, welche die Gruppe _SO2-CHr-CH2 <B>OH</B> ein- oder mehrmals enthalten, durch Um setzung mit starker Schwefelsäure in die sauren Schwefe'lsäureester überführen.
Die nach vorliegender Erfindung erhält lichen chromhaltigen Monoazofarbstoffe, wel che in der Seitenkette die anionoide Sulfon- säuregruppe tragen, besitzen eine sehr gute Wasserlöslichkeit und zeigen trotz der An wesenheit der Sulfonsäüregruppe im neutra len wie schwach sauren Färbebade ein. gutes Ziehvermögen.
Die neuen Farbstoffe sind hervorragend geeignet zum Färben von Wolle und Polyamid fasern. Infolge ihres guten Ziehvermögens aus neutralem oder schwach saurem Bade sind sie den bekannten, im Kern, Sulfonsäuregruppen enthaltenden Chromkomplexfarbstoffen über legen, die aus stark - saurem Bade gefärbt werden müssen, wobei das Fasermaterial lei det.
Die mit den Chromkomplexverbindungen erhaltenen Färbungen zeichnen sich durch hervorragende Nassechtheiten aus, da sich beim Färben die beim Färbevorgang entstehende -aS02 CH=CH.- Gruppe mit dem Wollkera:. tin verbindet.
<I>Beispiel</I> 13'7 Gewichtsteile 1-Aminobenzol-2-carbon- säure werden wie üblich diazotiert und mit 282 Gewichtsteilen 1-(4'ss,-,Oxyäthylsulfonyl)- 3-methyl@5-pyrazolon in Gegenwart überschüs siger Natriumcarbonatlösung gekuppelt.
Das entstandene Produkt wird mit Kochsalz völlig abgeschieden und abfiltriert. Der getrocknete Farbstoff wird .dann in 2700 Gewichtsteile Schwefelsäure 96prozentig bei 2U C einge tragen im.d nach erfolgter Lösung durch- Auf giessen auf Eis ausgefällt. Er wird abgesaugt und mit Kochsalzlösung neutral gewaschen.
Zur Chromierung wird der Farbstoff nun in 5000 Volumteilen Wasser mit 750 Volum- tei@len einer neutralen NatTiumchromsallicylat- lösung, die 28 Gewichtsteile Chrom enthält, zum Sieden erhitzt.
Nachbeendeter Ohromie- rang wird die Chromkomplexverbindung voll ständig mit. galiumchlorid ausgefällt, nach dem Erkalten abgesaugt und mit konzen- trierter Kaliumchlbridlösung ausgewaschen. Nach dem Trocknen stellt der Farbstoff ein gelbes Pulver dar, das in. Wasser leicht IÖS- #lZeh ist.
Er färbt Walle und Polyamidfasern in gelben Tönen von sehr guten Nassecht- heiten und guter bis sehr guter Lichtechtheit.
Process for the preparation of Ehrom-containing monoazo dyes It has been found that valuable new chromium-containing monoazo dyes are obtained if o-oxy- o'-carboxy-azo dyes which are free from nucleus sulfonic acid groups and which contain the group = SO2 CH2 CH2-OIS03H once or twice
converted into their complex chromium compounds by treatment with chromium complex compounds of aromatic o-oxycarboxylic acids (German patent writing No. 741462), in particular ohromalicylic acid or its salts, in a neutral or alkaline medium. In the finished chromium-containing dyes, the ratio of dye molecule to chromium atom is 2: 1 to 1: 1, preferably 2: 1.
The starting dyes used in the present process can be obtained in such a way that the -S02-CH2 CH2-0! SO3H group is incorporated into o-oxy-o'-carboxy-azo dyes which do not contain any nuclear sulfonic acid groups introduces twice.
The diazo and azo components can be prepared by conventional methods by reacting a diazotizable amino compound or an azo component with the group = SO2 CH2 CH2 OH with strong sulfuric acid, acidic sulfuric acid esters being formed. By diazo- ting and:
Subsequent coupling, the dye with the -S02 CHF CHe-OSO3H group can then be formed. However, azo dyes which contain the group _SO2-CHr-CH2 <B> OH </B> once or several times can also be converted into acidic sulfuric acid esters by reaction with strong sulfuric acid.
The chromium-containing monoazo dyes obtainable according to the present invention, which carry the anionic sulfonic acid group in the side chain, have very good water solubility and, despite the presence of the sulfonic acid group, show a neutral as well as weakly acidic dye bath. good drawability.
The new dyes are ideally suited for dyeing wool and polyamide fibers. As a result of their good drawability from neutral or weakly acidic baths, they are superior to the known chromium complex dyes containing sulfonic acid groups in the core, which have to be dyed from strongly acidic baths, with the fiber material suffering from.
The dyeings obtained with the chromium complex compounds are characterized by excellent wet fastness properties, since the -aS02 CH = CH.- group formed during the dyeing process with the Wollkera :. tin connects.
<I> Example </I> 13,7 parts by weight of 1-aminobenzene-2-carboxylic acid are diazotized as usual and with 282 parts by weight of 1- (4'ss, -, oxyethylsulfonyl) -3-methyl @ 5-pyrazolone in the presence Coupled excess sodium carbonate solution.
The resulting product is completely separated off with common salt and filtered off. The dried dyestuff is then precipitated in 2700 parts by weight of sulfuric acid 96 percent at 2 ° C. when the solution is complete and poured onto ice. It is suctioned off and washed neutral with sodium chloride solution.
For chroming, the dye is now boiled in 5000 parts by volume of water with 750 parts by volume of a neutral sodium chromium salicylate solution containing 28 parts by weight of chromium.
The chromium complex compound is completely with the finished earomy. Galium chloride precipitated, sucked off after cooling and washed out with concentrated potassium chloride solution. After drying, the dye is a yellow powder that is easily dissolved in water.
It dyes whale and polyamide fibers in yellow tones with very good wet fastness properties and good to very good light fastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE328656X | 1953-03-11 | ||
| CH327283T | 1954-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH328656A true CH328656A (en) | 1958-03-15 |
Family
ID=25736509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH328656D CH328656A (en) | 1953-03-11 | 1954-03-09 | Process for the preparation of chromium-containing monoazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH328656A (en) |
-
1954
- 1954-03-09 CH CH328656D patent/CH328656A/en unknown
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