CH280732A - Process for the preparation of a copper-containing disazo dye. - Google Patents
Process for the preparation of a copper-containing disazo dye.Info
- Publication number
- CH280732A CH280732A CH280732DA CH280732A CH 280732 A CH280732 A CH 280732A CH 280732D A CH280732D A CH 280732DA CH 280732 A CH280732 A CH 280732A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- parts
- dye
- disazo dye
- preparation
- Prior art date
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 9
- 229910052802 copper Inorganic materials 0.000 title claims description 9
- 239000010949 copper Substances 0.000 title claims description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000975 dye Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000004699 copper complex Chemical class 0.000 description 4
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 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
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension 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
- 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
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines kupferhaltigen Disazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen, kupferhaltigen Disazofarbstoff ge- langt, wenn man auf einen Disazofarbstoff s der Formel
EMI0001.0004
unter solchen Bedingungen kupferabgebende Mittel einwirken lässt, dass eine Aufspaltung der -() ,),lkvlgi,uppen unter Bildung des Bis- (o,o'-(lioxyazokupferkomplexes) erfolgt.
Der neue Farbstoff bildet ein dunkles Pul ver, das sieh in Wasser mit reinblauer Farbe löst und Baumwolle aus natriumsulfathaltigem Bade in reinen blauen Tönen von hoher Lieht- eelitlieit färbt.
Die beine vorliegenden Verfahren als Aus gangsstoffe dienenden Disazofarbstoffe der obigen Formel, welche zweekinässig in Form eines Alkalisalzes verwendet werden, können erhalten -erden, indem man ein tetrazotiertes 3,3'-Dialkoxy -4,4'-diamino-diplienyl, vorzugs weise tetrazotiertes 3,3'-Dimet.lioxy-4,
4.'-di- aininodihlienvl einerseits mit 1-Oxynaplit.lialin- 3,g-(lisulfonsä.lire und anderseits mit 2-(4'- Cai-l)oxynietlioxy plienvl )-amino-5-oxynaplitlia- lin-7-sulfonsätire kuppelt. Die Reihenfolge der Kupplung ist. beliebig.
Die Behandlung mit kupferabgebenden 'Mitteln erfolgt. in der Weise, dass unter Auf spaltung der -0-Alkylgruppen der Bis-(o,o'- dioxyazokupferkomplex) entsteht.
Methoden, die zu einer solchen entalkylierenden @ Kupfe reng führen, sind allgemein bekannt.. Beson- ders bewährt hat. sich zum Beispiel das Ver fahren, wonach unter Verwendung von Kup- fertetramminkomplexen in Gegenwart oder Abwesenheit von überschüssigem Ammoniak die Kupferung während einer bis mehrerer Stunden in der Nähe von<B>1000</B> in wässerigem Medium durchgeführt wird.
Die Kupferung kann aber auch mit Kupferacetat bzw. einer 'Mischung von Kupfersulfat und Natriumace- tat durchgeführt werden, indem man das Re- akt.ionsgemiseh oder den primär entstehenden Kupferkomplex, in welchem die Alkoxygrup- pen noch nielit aufgespalten worden sind, einige Stunden in trockenem Zustand bei Tem peraturen über 100" behandelt.
Beispiel: 24,4 Teile Dianisidin werden in 200 Teilen Wasser und 50 Teilen 30 o/oiger Salzsäure suspendiert und bei 0 bis 2" mit 14 Teilen Natriumnitrit tetrazotiert. Die klare Lösung der Tetrazoverbindung lässt man in möglichst raschem Tempo zu einer eiskalten Lösung von 32 Teilen 1-Oxynaphthalin-3,S-disulfonsäure und 30 Teilen wasserfreiem Natriumearbonat in 450 Teilen Wasser fliessen.
Nach etwa 15 Minuten hat die Bildung der Diazoazoverbin- dung stattgefunden, worauf man eine eiskalte Lösung von 40 Teilen 2-(4'-Carboxymethoxy- phenyl)-amino -5-oxynaphthalin-7-sulfonsäure und 10 Teilen wasserfreiem Natriumcarbonat in 300 Teilen Wasser zufliessen lässt. Nach einigen Stunden erwärmt man die Suspension des entstehenden Disazofarbstoffes auf 60 , gibt. etwa 150 Teile Natriumchlorid zu und fil triert den nun ausgefällten Farbstoff ab.
Eine bei 80 hergestellte Lösung dieser Farbstoffpaste in 2000 Teilen Wasser wird mit 52 Teilen Kupfersulfat und 200 Teilen kon zentriertem Ammoniak versetzt und einige Stunden bei 90 bis 100 gerührt, wobei die Kupferung unter Bildung der o,o'-Dioxyazo-
EMI0002.0010
unter solchen Bedingungen kupferabgebende Mittel einwirken lässt, dass eine Aufspaltung der -0-Alkylgruppen unter Bildung des Bis- (o,o'-dioxyazokupferkomplexes) erfolgt.
Der neue Farbstoff bildet ein dunkles Pul ver, das sich in Wasser mit reinblauer Farbe löst und Baumwolle aus natriumsulfathaltigem Bade in reinen blauen Tönen von hoher Licht echtheit. färbt. komplexe erfolgt. plan scheidet den kupfer haltigen Farbstoff durch Zugabe von 200 Tei len Natriumchlorid ab, filtriert und trocknet.
Vorteilhaft kann die Kupfertrog auch mit Kupferacetat bzw. einer Mischung von Kup fersulfat und Natriumaeetat durchgeführt werden, z. B. indem man das Reaktionsgemiseh oder den primär entstandenen Komplex trock net und einige Stunden auf etwa 12.5 erwärmt.
Process for the preparation of a copper-containing disazo dye. It has been found that a valuable, copper-containing disazo dye is obtained by using a disazo dye s of the formula
EMI0001.0004
lets copper-releasing agents act under such conditions that splitting of the - (),), lkvlgi, lobes takes place with the formation of the bis (o, o '- (lioxyazo copper complex).
The new dye forms a dark powder that dissolves in water with a pure blue color and dyes cotton from a bath containing sodium sulfate in pure blue tones of high lightness.
The present process as starting materials serving disazo dyes of the above formula, which are used bifurcated in the form of an alkali salt, can be obtained by adding a tetrazotized 3,3'-dialkoxy -4,4'-diamino-diplienyl, preferably tetrazotized 3,3'-dimet.lioxy-4,
4 .'- di- aininodihlienvl on the one hand with 1-oxynaplit.lialin- 3, g- (lisulfonsä.lire and on the other hand with 2- (4'- Cai-l) oxynietlioxy plienvl) -amino-5-oxynaplitlia- lin-7- sulfonic acid couplings. The order of coupling is. any.
The treatment with copper-releasing agents takes place. in such a way that the bis (o, o'-dioxyazo copper complex) is formed with splitting of the -0-alkyl groups.
Methods which lead to such dealkylating @ Kupfe reng are well known. Particularly proven. For example, the method according to which coppering is carried out in the vicinity of 1000 in an aqueous medium for one to several hours using copper tetrammine complexes in the presence or absence of excess ammonia.
The coppering can, however, also be carried out with copper acetate or a mixture of copper sulfate and sodium acetate by adding the reaction mixture or the primary copper complex in which the alkoxy groups have not yet been split for a few hours treated in a dry state at temperatures over 100 ".
Example: 24.4 parts of dianisidine are suspended in 200 parts of water and 50 parts of 30% hydrochloric acid and tetrazotized at 0 to 2 "with 14 parts of sodium nitrite. The clear solution of the tetrazo compound is allowed to form an ice-cold solution of 32 at the fastest possible rate Parts of 1-oxynaphthalene-3, S-disulfonic acid and 30 parts of anhydrous sodium carbonate flow in 450 parts of water.
After about 15 minutes, the formation of the diazoazo compound has taken place, whereupon an ice-cold solution of 40 parts of 2- (4'-carboxymethoxyphenyl) -amino -5-oxynaphthalene-7-sulfonic acid and 10 parts of anhydrous sodium carbonate in 300 parts of water can flow. After a few hours, the suspension of the disazo dye formed is heated to 60%. about 150 parts of sodium chloride and fil triert from the now precipitated dye.
A solution prepared at 80 of this dye paste in 2000 parts of water is mixed with 52 parts of copper sulfate and 200 parts of concentrated ammonia and stirred for a few hours at 90 to 100, the coppering to form the o, o'-dioxyazo-
EMI0002.0010
lets copper-donating agents act under such conditions that splitting of the -0-alkyl groups with formation of the bis- (o, o'-dioxyazo copper complex) takes place.
The new dye forms a dark powder that dissolves in water with a pure blue color, and cotton from a bath containing sodium sulfate in pure blue tones with a high level of lightfastness. colors. complex takes place. plan separates the copper-containing dye by adding 200 parts of sodium chloride, filtering and drying.
The copper trough can advantageously also be carried out with copper acetate or a mixture of copper sulfate and sodium acetate, e.g. B. by net dry the reaction mixture or the primarily formed complex and heated to about 12.5 for a few hours.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH277658T | 1949-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH280732A true CH280732A (en) | 1952-01-31 |
Family
ID=4481343
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH277658D CH277658A (en) | 1949-08-05 | 1949-08-05 | Process for the preparation of a copper-containing disazo dye. |
| CH280732D CH280732A (en) | 1949-08-05 | 1949-08-05 | Process for the preparation of a copper-containing disazo dye. |
| CH280731D CH280731A (en) | 1949-08-05 | 1949-11-10 | Process for the preparation of a copper-containing disazo dye. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH277658D CH277658A (en) | 1949-08-05 | 1949-08-05 | Process for the preparation of a copper-containing disazo dye. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH280731D CH280731A (en) | 1949-08-05 | 1949-11-10 | Process for the preparation of a copper-containing disazo dye. |
Country Status (4)
| Country | Link |
|---|---|
| CH (3) | CH277658A (en) |
| DE (1) | DE889662C (en) |
| FR (1) | FR1023892A (en) |
| GB (1) | GB674707A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2816102A (en) * | 1953-02-12 | 1957-12-10 | Ciba Ltd | Metalliferous azo dyestuffs |
| BE541338A (en) * | 1954-09-17 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE515468C (en) * | 1929-02-19 | 1931-01-09 | I G Farbenindustrie Akt Ges | Process for the preparation of ª ‰ -Naphthylaminophenoxyfettsaeuren |
| GB333573A (en) * | 1929-05-10 | 1930-08-11 | Ig Farbenindustrie Ag | Process for the manufacture of substantive ª¤-carboxyazo dyestuffs containing copper |
| GB352956A (en) * | 1930-04-14 | 1931-07-14 | Ig Farbenindustrie Ag | Process for the manufacture of substantive dyeing disazo dyestuffs containing copper |
-
1949
- 1949-08-05 CH CH277658D patent/CH277658A/en unknown
- 1949-08-05 CH CH280732D patent/CH280732A/en unknown
- 1949-11-10 CH CH280731D patent/CH280731A/en unknown
- 1949-11-28 DE DEC211A patent/DE889662C/en not_active Expired
-
1950
- 1950-07-27 GB GB18845/50A patent/GB674707A/en not_active Expired
- 1950-07-31 FR FR1023892D patent/FR1023892A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB674707A (en) | 1952-06-25 |
| CH277658A (en) | 1951-09-15 |
| FR1023892A (en) | 1953-03-25 |
| CH280731A (en) | 1952-01-31 |
| DE889662C (en) | 1953-09-14 |
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