DE1154211B - Process for the production of cobalt-containing monoazo dyes - Google Patents
Process for the production of cobalt-containing monoazo dyesInfo
- Publication number
- DE1154211B DE1154211B DEB38188A DEB0038188A DE1154211B DE 1154211 B DE1154211 B DE 1154211B DE B38188 A DEB38188 A DE B38188A DE B0038188 A DEB0038188 A DE B0038188A DE 1154211 B DE1154211 B DE 1154211B
- Authority
- DE
- Germany
- Prior art keywords
- cobalt
- dyes
- oxynaphthalene
- alkyl
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 14
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims description 9
- 229910017052 cobalt Inorganic materials 0.000 title claims description 7
- 239000010941 cobalt Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 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 description 4
- -1 cobalt complex compounds Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000987 azo dye Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000010186 staining Methods 0.000 claims 1
- 210000002268 wool Anatomy 0.000 description 4
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GWSQAGVGSHXRJK-UHFFFAOYSA-N 4-amino-5-methoxy-n,2-dimethylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(OC)=C(N)C=C1C GWSQAGVGSHXRJK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 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
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RPILSQRRFFWGQN-UHFFFAOYSA-N n-methylmethanamine;naphthalene Chemical compound CNC.C1=CC=CC2=CC=CC=C21 RPILSQRRFFWGQN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000009466 transformation Effects 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
- C09B45/20—Monoazo compounds containing cobalt
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von kobalthaltigen Monoazofarbstoffen Es wurde gefunden, daß man wertvolle kobalthaltige Monoazofarbstoffe erhält, wenn man diazotierte Aminobenzole der allgemeinen Formel worin X eine Alkyl- oder eine Alkoxygruppe oder ein Halogenatom, Alk eine Alkylgruppe, Y und Z Wasserstoff, Alkyl- oder Arylgruppen bedeuten, mit sulfonsäuregruppenfreien Derivaten des 2-Oxynaphthalins kuppelt, die als Substituenten Acyl-, Carboxalkyl- oder Arylsulfonylaminogruppen tragen, und die erhaltenen o-Oxy-o'-alkoxy-Monoazofarbstoffe nach an sich bekannten Verfahren in Kobaltkomplexverbindungen der entsprechenden o,o'-Dioxyazofarbstoffe überführt, die auf 2 Azofarbstof moleküle etwa 1 Kobaltatom enthalten.Process for the preparation of cobalt-containing monoazo dyes It has been found that valuable cobalt-containing monoazo dyes are obtained if diazotized aminobenzenes of the general formula are used wherein X is an alkyl or an alkoxy group or a halogen atom, Alk is an alkyl group, Y and Z are hydrogen, alkyl or aryl groups, couples with sulfonic acid group-free derivatives of 2-oxynaphthalene which have acyl, carboxalkyl or arylsulfonylamino groups as substituents, and the O-oxy-o'-alkoxy-monoazo dyes obtained are converted by processes known per se into cobalt complex compounds of the corresponding o, o'-dioxyazo dyes which contain about 1 cobalt atom per 2 azo dye.
Geeignete Azokomponenten sind z. B. das 1-Acetylamino-6-oxynaphthalin, das 1-(Carbomethoxyamino)-7-oxynaphthalin, das 1-(Benzolsulfonylamino)-7-oxynaphthalin oder das 1-(N-Methyl-N-p-toluolsulfonyl)-amino-6-oxynaphthalin.Suitable azo components are, for. B. 1-acetylamino-6-oxynaphthalene, 1- (carbomethoxyamino) -7-oxynaphthalene, 1- (benzenesulfonylamino) -7-oxynaphthalene or 1- (N-methyl-N-p-toluenesulfonyl) -amino-6-oxynaphthalene.
Die Diazotierung und Kupplung erfolgt in üblicher Weise. Die Umwandlung in die Kobaltkomplexverbindungen kann z. B. nach den in den deutschen Patentschriften 715 082 oder 715 948 oder in der französischen Patentschrift 836 257 beschriebenen Verfahren vorgenommen werden.The diazotization and coupling are carried out in the customary manner. The transformation in the cobalt complex compounds can, for. B. according to the in the German patents 715 082 or 715 948 or in French patent 836 257 Procedures are made.
Die so erhältlichen kobalthaltigen Farbstoffe zeichnen sich durch hohe Echtheiten und gutes Egalisiervermögen aus und sind insbesondere zum Färben von Wolle und Polyamidfasern aus neutralem oder schwach saurem Bade geeignet.The cobalt-containing dyes obtainable in this way are distinguished by high fastness properties and good leveling properties and are particularly useful for dyeing Suitable for wool and polyamide fibers from neutral or slightly acidic baths.
Sie zeigen auf Wolle in schwach saurem Bade ein wesentlich besseres Egalisiervermögen als die entsprechenden Chromkomplexverbindungen der gleichen Farbstoffe, die aus Beispiel 3 der USA.-Patentschrift 2 623 871- bekannt sind.They show a much better result on wool in a weakly acidic bath Leveling power than the corresponding chromium complex compounds of the same dyes, which are known from Example 3 of US Pat. No. 2,623,871.
Die im Beispiel genannten Teile sind Gewichtsteile.
22 Teile des so erhaltenen Monoazofarbstoffs werden mit einer Lösung von 6 Teilen Kobalt(II)-chlorid (CoC12 - 6 H20) in 200 Teilen Acetamid 5 Stunden auf 130°C erhitzt. Dann trägt man das Gemisch in 2000 Teile Wasser ein, fällt den kobalthaltigen Farbstoff mit 200 Teilen Natriumchlorid aus, saugt ihn ab, wäscht ihn mit etwas Wasser und trocknet ihn bei 80°C.22 parts of the monoazo dye thus obtained are mixed with a solution of 6 parts of cobalt (II) chloride (CoC12 - 6 H20) in 200 parts of acetamide for 5 hours heated to 130 ° C. Then the mixture is introduced into 2000 parts of water, the falls cobalt-containing dye with 200 parts of sodium chloride, sucks it off, washes with a little water and dry it at 80 ° C.
Der Farbstoff färbt Wolle und Polyamidfasern aus schwach saurem Bade in rotstichigblauen Tönen von sehr guten Echtheiten.The dye dyes wool and polyamide fibers from weakly acidic baths in reddish blue shades of very good fastness properties.
In entsprechender Weise kann man die folgenden kobalthaltigen Farbstoffe herstellen:The following cobalt-containing dyes can be used in a corresponding manner produce:
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB38188A DE1154211B (en) | 1955-12-07 | 1955-12-07 | Process for the production of cobalt-containing monoazo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB38188A DE1154211B (en) | 1955-12-07 | 1955-12-07 | Process for the production of cobalt-containing monoazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1154211B true DE1154211B (en) | 1963-09-12 |
Family
ID=6965418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB38188A Pending DE1154211B (en) | 1955-12-07 | 1955-12-07 | Process for the production of cobalt-containing monoazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1154211B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623871A (en) * | 1950-04-27 | 1952-12-30 | Geigy Ag J R | Chromium containing monoazo dyestuffs |
-
1955
- 1955-12-07 DE DEB38188A patent/DE1154211B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623871A (en) * | 1950-04-27 | 1952-12-30 | Geigy Ag J R | Chromium containing monoazo dyestuffs |
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