CH257113A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH257113A CH257113A CH257113DA CH257113A CH 257113 A CH257113 A CH 257113A CH 257113D A CH257113D A CH 257113DA CH 257113 A CH257113 A CH 257113A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- acid
- new
- chromium
- aminophenol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- 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 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052804 chromium Inorganic materials 0.000 claims description 9
- 239000011651 chromium Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 4
- -1 methylglycol ester Chemical class 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 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
- 239000004202 carbamide Substances 0.000 claims 1
- 150000001845 chromium compounds Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 9
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 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 description 3
- 239000000987 azo dye Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 2
- 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
- 238000009835 boiling Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 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
- 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
- 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-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
- 229940037003 alum Drugs 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AQKPVEGVPVVHCV-UHFFFAOYSA-N n-(3-amino-4-hydroxyphenyl)benzamide Chemical compound C1=C(O)C(N)=CC(NC(=O)C=2C=CC=CC=2)=C1 AQKPVEGVPVVHCV-UHFFFAOYSA-N 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
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000005406 washing 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
- 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 Monoazofarbatoffes. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von 1Vlono- azofarbstoffan; es ist dadurch gekennzeich net, dass man diazotierte o-Aminophenol- :
sulfonsäuren oder deren kernsubstituierte Derivate mit o-Alkylglyko.lestern der 7-Oxy- iiaphthyl-l-carbamidsäure kuppelt und die <U>so</U> erhaltenen Azofarbstoffe gegebenenfalls in ihre Chromk omplexverbindungen über- f ührt.
Als Diazokomponenten können z. B. fol gende Verbindungen angewandt werden: 2-Aminophenol - 4 - sulfonsäure, 2 - Amino- phenol-4,6-dis.ulfonsäure, 4-Chlor-2-amino- phenol-6-sulfonsäure, 6-Chlor-2-:
aminophenol- 4-sul'fonsäure, 3,4,6-Trichlor-2-aminophenol- 5 - sulf onsäure, 4 - Nitro - 2 - aminophenol - 6 - sulfonsäure, 6-Nitro-2-aminopheno,1-4-sulfon- s i iiure, 4-Chlor-2-aminophenol-5-sulfonsäure, 4 -1Vlethyl - 2 - aminophenol - 5 -sulfonsäure,
4- Benzoylamino - 2 - aminophenol - 6-sulf onsäure. 6 - Benzoylamino - 2 - aminophenol -14- !sulfon- säure, 2-Aminopheno!1:4-carbamidsäureäthyl- ester - 6 -sulfonsäure, 2 - Aminophenol - 6 - carbamidsäureäthylester-4-sulfonsäure usw.
Die neuen Kupplungskomponenten kön nen durch Einwirkenlassen von Chlorameisen säure - alkylglykolestern auf 1,7 - Amino- naphthol in Gegenwart eines Neutralisations- mittels, wie z. B. Soda oder Kreide, erhalten werden; es sind in Wasser schwer lösliche, in Alkohol und Aceton leicht lösliche Körper.
Die wie üblich erfolgende Kupplung der neuen Verbindungen mit den in Betracht kommenden Diazo-körpern liefert die Azo- farb toffe in guten Ausbeuten.
Die neuen, gut kristallisierenden Farb stoffe sind ausgezeichnete Nachchromie- rungsfarbstoffe, von welchen sich die meisten auch für das Einbadchromfärbeverfahren vorzüglich eignen. In Substanz können sie alle in wertvolle, gut kristallisierte Chrom- komplexverbindun.gen umgewandelt 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 Walkeehtheit. Ihre Chromkomplexverbin- dungen färben die Wolle aus saurem Bade in ähnlichen, aber lebhafteren Tönen von be merkenswerter Echtheit bei gutem Egalisie- runbvermögen.
Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines neuen ehromier- baren 14lonoa.zofarbstoffes und ist dadurch gekennzeichnet, dass man diazotierte 4-Chlor- 2-aminophenol-6-sulfonsäure mit 1-(7-Oxy- naphthyl) - carbamidsäure - methylglykolestem vereinigt.
Beispiel: 22,4 Gewiehtsteile 4-Chlor-2-aminophenol- 6-sulfonsäure werden diazotiert und mit 26,1 Gewichtsteilen 1 - (7 - Oxynaphthyl)- carbamidsäure-methylglykoles.ter, gelöst in 300 Teilen Wasser mit 4 Gewichtsteilen Na- triiunhyd@roxyd, in Gegenwart von über- schüssiger Soda, gekuppelt.
Der Farbstoff wird durch Aussalzen und Abfiltrieren ge wonnen und stellt getrocknet ein dunkel violettes Pulver dar, welches sich in konzen trierter Schwefelsäure mit bläulichroter Farbe löst.
Der Farbstoff ist ein ausgezeich- net neutral ziehender Einbadchromfarbstoff und gibt auf Wolle sehr gut wasch-, walk und ,lichtechte Ausfärbungen von lebhaften blaugrauen Tönen.
Der als Kupplungskomponente verwen dete wasserfreie 1- (7 - Oxynaphthyl)-carb- amidsäuremethyl'glykoI.ester sschmilzt- bei u6 C und wird durch Umsetziung von Chlor- ameisensäure-methyl'gdykolester (gp,amn,: 58 bis 59 C) mit 1,7-Aminonaphthol erhalten.
Zur Herstellung des Chromkomplexes wird eine wie oben erhaltene Farbstoffmenge in einer mit 75 Gewichtsteilen 10 %iger Sch\vefelsäure versetzten Lösung von 75 Ge- wichtsteilen Chromalaun in 1600 Teilen Wasser suspendiert und 24 Stunden am Rüäkflusskühler zum Sieden erhitzt.
Nach dem Erkalten wird der in gut kristallisierter Form ausgeschiedene Chromkomplex abfil- triert. Trocken stellt er ein dunkelviolettes Pulver dar, welches sich in konzentrierter Schwefelsäure mit bläulichroter Farbe löst. Die schwefelsauren Ausfärbungen des neuen Chromkomplexes sind blau, von ausgezeich- netex Wasch- und Walkechtheit und guter S.Liehtechtheit.
Process for the preparation of a monoazo carbate. The subject of the present invention is a process for the preparation of 1Vlono azo dye; it is characterized in that diazotized o-aminophenol:
sulfonic acids or their nucleus-substituted derivatives with o-alkylglyco.lesters of 7-oxy-iiaphthyl-1-carbamic acid and the azo dyes obtained in this way are optionally converted into their chromium complex compounds.
As diazo components, for. B. the following compounds are used: 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-aminopheno, 1-4-sulfone - acid, 4-chloro-2-aminophenol-5-sulfonic acid, 4 -1Vlethyl - 2 - aminophenol - 5-sulfonic acid,
4- Benzoylamino - 2 - aminophenol - 6-sulfonic acid. 6 - Benzoylamino - 2 - aminophenol -14-! Sulfonic acid, 2-aminopheno! 1: 4-carbamic acid ethyl ester - 6-sulfonic acid, 2 - aminophenol - 6 - carbamic acid ethyl ester-4-sulfonic acid etc.
The new coupling components can NEN by allowing chloroformic acid - alkyl glycol esters to 1,7 - amino naphthol in the presence of a neutralizing agent, such as. B. soda or chalk can be obtained; they are sparingly soluble in water, easily soluble in alcohol and acetone.
The coupling of the new compounds with the diazo bodies in question, which is carried out as usual, gives the azo dyes in good yields.
The new, well-crystallizing dyes are excellent post-chrome plating dyes, most of which are also ideally suited for the single-bath chrome dyeing process. In substance, they can all be converted into valuable, well-crystallized chromium complex compounds.
The chromium-free dyes produce gray, gray-blue, blue and olive shades of good lightness and very good wash and fulling resistance on wool when dyed using the post-chrome plating or single-bath chrome process. Their chromium complex compounds dye the wool from an acid bath in similar but livelier shades of noticeable fastness with good leveling ability.
The present patent relates to a process for the production of a new honorable 14lonoa.zo dye and is characterized in that diazotized 4-chloro-2-aminophenol-6-sulfonic acid is mixed with 1- (7-oxynaphthyl) -carbamic acid-methylglycol esters united.
Example: 22.4 parts by weight of 4-chloro-2-aminophenol-6-sulfonic acid are diazotized and treated with 26.1 parts by weight of 1- (7-oxynaphthyl) -carbamic acid methylglycols, dissolved in 300 parts of water with 4 parts by weight of sodium trihydrate @roxyd, in the presence of excess soda, coupled.
The dye is obtained by salting out and filtering off and, when dried, is a dark purple powder which 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 lightfast colorations of lively blue-gray tones to wool.
The anhydrous methyl 1- (7-oxynaphthyl) -carbamic acid methyl'glycol ester used as the coupling component melts at 6 ° C. and is reacted with methyl chloroformate (gp, amn ,: 58 to 59 ° C.) 1,7-aminonaphthol obtained.
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 schulic acid have been added and heated to boiling for 24 hours on a reflux condenser.
After cooling, the chromium complex, which has separated out in a well-crystallized form, is filtered off. When dry it is a dark purple powder that dissolves in concentrated sulfuric acid with a bluish red color. The sulfuric acid colorations of the new chromium complex are blue, excellent washing and boiling fastness and good light fastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH257113T | 1947-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH257113A true CH257113A (en) | 1948-09-30 |
Family
ID=4472020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH257113D CH257113A (en) | 1947-04-29 | 1947-04-29 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH257113A (en) |
-
1947
- 1947-04-29 CH CH257113D patent/CH257113A/en unknown
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