CH243335A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH243335A CH243335A CH243335DA CH243335A CH 243335 A CH243335 A CH 243335A CH 243335D A CH243335D A CH 243335DA CH 243335 A CH243335 A CH 243335A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- aminophenol
- new
- sulfonic acid
- blue
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 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 4
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 13
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- YCTAOQGPWNTYJE-UHFFFAOYSA-N 3-amino-5-chloro-2-hydroxybenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC(S(O)(=O)=O)=C1O YCTAOQGPWNTYJE-UHFFFAOYSA-N 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 150000001845 chromium compounds Chemical class 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 description 8
- 239000011651 chromium Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N ortho-hydroxyaniline Natural products NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 230000002378 acidificating effect Effects 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- -1 o-aminophenol sulfonic acids Chemical class 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 1
- RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- QGTXBWMKRGHPDD-UHFFFAOYSA-N 3-amino-5-chloro-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(Cl)=C1O QGTXBWMKRGHPDD-UHFFFAOYSA-N 0.000 description 1
- HTYRTGGIOAMLRR-UHFFFAOYSA-N 5-amino-4-hydroxybenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O HTYRTGGIOAMLRR-UHFFFAOYSA-N 0.000 description 1
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 1
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UWIMIKCSKLMQHZ-UHFFFAOYSA-N N-(3-amino-2-hydroxyphenyl)benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=CC(=C1O)N UWIMIKCSKLMQHZ-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 235000011127 sodium aluminium sulphate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Honoazofarbstofes. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von Mono- azofarbstoffen, darin bestehend, da$ man di- azotierte o-Aminophenolsulfonsäuren oder ihre kernsubstituierten Derivate mit a-(7 Oxynaphthyl)
-carbamidsäurealkylestern ver einigt und die so erhältlichen Azofarbstoffe gegebenenfalls in ihre Chromkomplexverbin- dungen überführt.
Als Diazokomponenten können zum Bei spiel folgende Verbindungen angewandt wer den: 2-Aminophenol-4-sulfonsäure, 2-Amino- phenol - 4,6 - disulf onsäure, 4 -Chlor - 2-amino- phenol-6-sulfonsäure, 6-Chlor-2-aminophenol- 4-sulfonsäure, 3,4,6-Trichlor-2-aminophenol- 5-sulfonsäure, 4-Nitro-2-aminophenol-6-sul- fonsKure,
6-Nitro-2-aminophenol-4-sulfon- säure, 4-Chlor-2-aminophenol-5-sulfonsäure, 4 - Methyl - 2 - aminophenol - 5 - sulf onsäure, 4 Benzoylamino - 2 - aminophenol -6-sulf onsäure, 6 - Benzoylamino - 2 - aminophenol - 4 - sulfon- säure,
2-Aminophenol-4-earbamidsäureäthyl- ester - 6 - sulfonsäure, 2 -Aminophenol - 6-carb- amidsäureäthylester-4-sulfonsäure usw. Die zur Kupplung verwendeten neuen Azokomponenten können durch Einwirken lassen von Chlorameisensäurealkylestern auf in Wasser oder in einem organischen indif ferenten Lösungsmittel suspendiertes 1,7 Aminonaphthol in Gegenwart eines Neutrali- sationsmittels, wie z. B.
Soda oder Kreide, in guter Ausbeute erhalten werden. Die a-(7- Oxynaphthyl) - carbamidsäurealkylester sind in Wasser schwer lösliche, in Alkohol und Aceton leicht lösliche, kristallisierte Körper mit folgenden charakteristischen Schmelz punkten:
a-(7-Ogynaphthyl)-carbamidsäuremethyl- ester F: 104 , a- (7 -Oxynaphthyl) - carbamidsäureäthyl- ester F: 118 bis 119 , a - (7 - Oxynaphthyl) - carbamidsäure - (@- chloräthylester) F: 116 , a - (7 - Oxynaphthyl) - carbamidsäure-n-bu- tylester F: 154 bis 155 Zersetzung.
Die Kupplung der neuen Verbindungen mit den in Betracht kommenden Diazokörpern erfolgt wie üblich und liefert die Azofarb- stoffe in guten Ausbeuten.
Die neuen, gut kristallisierenden Farb stoffe sind ausgezeichnete Nachchromierungs- farbstoffe, und die meisten von ihnen eignen sich vorzüglich für das Einbadchrom-Färbe- verfahren. Zudem können sie alle in Sub stanz in wertvolle, ebenfalls gut kristallisie rende Chromkomplexverbindungen umgewan delt werden, wofür sie aus dem Grund be sonders geeignet sind, weil die Carbamid- säureestergruppen in mineralsaurem Mittel nicht verseift werden.
Die chromfreien Farbstoffe liefern auf Wolle nach dem Nachchromierungs- oder nach dem Einbadchromverfahren gefärbt graue, graublaue, blaue und olive Töne von guter Licht- und sehr guter Wasch- und Walkechtheit. Die Chromkomplexverbindun- gen färben die Wolle in saurem Bade in ähn lichen, aber lebhafteren Tönen von bemer kenswerter Echtheit bei gutem Egalisie- rungsvermögen.
Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines neuen chromier- baren Monoazofarbstoffes und ist dadurch gekennzeichnet, dass man diazotierte 4-Chlor- 2-aminophenol-6-sulfonsäure mit a-(7-Oxy- naphthyl) - carbamidsäuremethylester verei nigt.
<I>Beispiel:</I> 22,4 Gewichtsteile 4-Chlor-2-aminophenol- 6-sulfonsäure werden diazotiert und mit 21,7 Gewichtsteilen a-(7-Oxynaphthyl)-carbamid- säuremethylester, gelöst in 300 Teilen Was ser mit 4 Gewichtsteilen Natriumhydroxyd, in Gegenwart der berechneten Menge Na triumcarbonat, gekuppelt.
Der neue Farb stoff wird durch Aussalzen und Abfiltrieren gewonnen. Trocken stellt er ein dunkelviolet tes Pulver dar, welches sich in konzentrierter Schwefelsäure mit bläulichroter Farbe löst. Der Farbstoff ist ein ausgezeichnet neutral ziehender Einbadchromfarbstoff und gibt auf Wolle sehr gut wasch-, walk- und licht echte Ausfärbungen von lebhaften blau grauen Tönen.
Zur Herstellung des Chromkomplexes wird eine wie oben erhaltene Farbstoffmenge in einer mit 75 Gewichtsteilen 10%iger Sehive- felsäure versetzten Lösung von 75 Gewichts teilen Chromalaun in 1600 Teilen Wasser suspendiert und 20 Stunden am R,ückfluss- kühler zum Sieden erhitzt. Nach dem Erkal ten auf Zimmertemperatur wird der in gut kristallisierter Form vollständig ausgeschie dene Chromkomplex abfiltriert. . Trocken stellt er ein dunkelviolettes Pulver dar, wel ches sich in konzentrierter Schwefelsäure mit bläulichroter Farbe löst.
Die schwefelsauren Ausfärbungen des neuen Chromkomplexes sind blau, von ausgezeichneter Wasch- und Walkechtheit und guter Lichtechtheit.
Process for the preparation of a honoazo dye. The present invention relates to a process for the preparation of monoazo dyes, which consists in that one diazotized o-aminophenol sulfonic acids or their ring-substituted derivatives with a- (7 oxynaphthyl)
-carbamidsäurealkylestern united and the thus obtainable azo dyes optionally converted into their chromium complex compounds.
The following compounds, for example, can be used as diazo components: 2-aminophenol-4-sulfonic acid, 2-aminophenol-4,6-disulfonic acid, 4-chloro-2-aminophenol-6-sulfonic acid, 6-chloro -2-aminophenol- 4-sulfonic acid, 3,4,6-trichloro-2-aminophenol- 5-sulfonic acid, 4-nitro-2-aminophenol-6-sulfonic acid,
6-nitro-2-aminophenol-4-sulfonic acid, 4-chloro-2-aminophenol-5-sulfonic acid, 4 - methyl - 2 - aminophenol - 5 - sulfonic acid, 4 benzoylamino - 2 - aminophenol -6-sulfonic acid , 6 - Benzoylamino - 2 - aminophenol - 4 - sulfonic acid,
2-aminophenol-4-earbamidsäureäthyl- ester - 6 - sulfonic acid, 2-aminophenol - 6-carb- amidsäureäthylester-4-sulfonic acid, etc. The new azo components used for coupling can be ferenten by allowing chloroformate to act on in water or in an organic indif 1.7 aminonaphthol suspended in solvent in the presence of a neutralizing agent, such as B.
Soda or chalk, can be obtained in good yield. The a- (7-oxynaphthyl) - carbamic acid alkyl esters are sparingly soluble in water, easily soluble in alcohol and acetone, crystallized bodies with the following characteristic melting points:
a- (7-Ogynaphthyl) -carbamic acid methyl ester F: 104, a- (7-oxynaphthyl) - carbamic acid ethyl ester F: 118 to 119, a - (7 - oxynaphthyl) - carbamic acid - (@ - chloroethyl ester) F: 116 , a - (7 - Oxynaphthyl) - carbamic acid n-butyl ester F: 154 to 155 decomposition.
The coupling of the new compounds with the diazo bodies in question takes place as usual and gives the azo dyes in good yields.
The new, well-crystallizing dyes are excellent post-chrome plating dyes, and most of them are ideally suited for the single-bath chrome dyeing process. In addition, they can all be converted in substance into valuable, also well-crystallizing chromium complex compounds, for which they are particularly suitable because the carbamic acid ester groups are not saponified in mineral acidic agents.
The chromium-free dyes produce gray, gray-blue, blue and olive tones of good lightfastness and very good wash and milled fastness on wool after the chromium plating or single-bath chrome process. The chromium complex compounds color the wool in an acidic bath in similar but livelier shades of remarkable authenticity with good leveling power.
The present patent relates to a process for the production of a new chromable monoazo dye and is characterized in that diazotized 4-chloro-2-aminophenol-6-sulfonic acid is combined with methyl α- (7-oxynaphthyl) carbamate.
<I> Example: </I> 22.4 parts by weight of 4-chloro-2-aminophenol-6-sulfonic acid are diazotized and mixed with 21.7 parts by weight of methyl a- (7-oxynaphthyl) -carbamidate, dissolved in 300 parts of water with 4 parts by weight of sodium hydroxide, in the presence of the calculated amount of sodium carbonate, coupled.
The new dye is obtained by salting out and filtering off. When dry, it is a dark purple powder that dissolves in concentrated sulfuric acid with a bluish-red color. The dye is an excellent, neutral, single-bath chrome dye and gives very good wash-, mill- and light-fast coloring of lively blue-gray tones on wool.
To prepare the chromium complex, an amount of dye obtained as above is suspended in a solution of 75 parts by weight of chromium alum in 1600 parts of water to which 75 parts by weight of 10% strength sodium alum have been added and heated to boiling for 20 hours on a reflux cooler. After cooling down to room temperature, the chromium complex, which is completely precipitated in a well-crystallized form, is filtered off. . When dry it is a dark purple powder which dissolves in concentrated sulfuric acid with a bluish red color.
The sulfuric acid coloring of the new chromium complex is blue, of excellent wash and milled fastness and good light fastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH243335T | 1944-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH243335A true CH243335A (en) | 1946-07-15 |
Family
ID=4463507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH243335D CH243335A (en) | 1944-09-01 | 1944-09-01 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH243335A (en) |
-
1944
- 1944-09-01 CH CH243335D patent/CH243335A/en unknown
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