CH277658A - 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
- CH277658A CH277658A CH277658DA CH277658A CH 277658 A CH277658 A CH 277658A CH 277658D A CH277658D A CH 277658DA CH 277658 A CH277658 A CH 277658A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- dye
- parts
- disazo dye
- alkyl groups
- Prior art date
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 10
- 229910052802 copper Inorganic materials 0.000 title claims description 10
- 239000010949 copper Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 7
- 239000000975 dye Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000004699 copper complex Chemical class 0.000 claims description 3
- 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 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 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
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 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
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 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
- 239000000203 mixture Substances 0.000 description 2
- 238000007747 plating Methods 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
- 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
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003086 colorant Substances 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
- -1 disazo carbate Chemical compound 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate 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
<B>Verfahren zur Herstellung eines kupferhaltigen</B> Disazofarbatoffes. 1:s wurde gefunden, dass man zu einem wertvollen, kupferhaltigen Disazofarbstoff ge- langt, wenn man auf einen Disazofarbstoff der Formel
EMI0001.0005
unter solchen Bedingungen kupferabgebende Mittel einwirken lässt, dass eine Aufspaltung der --0-Alkylgruppen unter Bildung des Bis-(o,o'-(lioxyazokupferkoinplexes) erfolgt.
Der neue Farbstoff bildet ein dunkles Pul ver, das sich in Wasser mit neinblauer Farbe löst und Baumwolle aus natriumsulfathalti- gein Bade in reinen blauen Tönen von hoher Lichtechtheit. färbt.
Die beim vorliegenden Verfahren als Aus gangsstoffe dienenden Disazofarbstoffe den obigen Formel, welche zweckmässig,- in Form eines 4lkalisalzes verwendet werden, können erhalten werden, indem man ein tetrazotiertes 3,3'-Dialkoxy -4,4'-diaminodiphenvl, vorzugs weise tetrazotiertes 3,3'-Dimet.roxv-4,4'-di- aminodiphenyl einerseits mit l.-Oxynaphthalin- 4,
8-disttlfonsäure und anderseits mit 2-(4'- ('arboxyniethoxyphenpl.) - amino - 5 - oxynaph- thaliri-7-stilfonsätire 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. Me thoden, die zu einer solchen entalkvliererideri Kupferung führen, sind allgemein bekannt. Besonders bewährt hat sich z.
B. 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 100 in wässerigem Medium durchgeführt wird.
Die Kupferung kann aber auch mit Kupferacetat bzw. einer Mischung von Kupfersulfat und NTatrium- aeetat durehgefü hrt. werden, indem man das Reaktionsgemiseh oder den primär entstehen den Kupferkomplex, in welchem die Alkox@- gruppen noch nicht aufgespalten worden sind, einige Stunden in troekenenr. Zustande bei Temperaturen über 100 behandelt..
<I>Beispiel:</I> 24,1 Teile Dianisidin werden in ,\300 Teilen Wasser und 50 Teilen 301,10i-er Salzsäure suspendiert und bei 0 bis 2 mit 14 Teilen Natriumnitrit tetrazotiert. Die klare Lösung der Tetrazoverbindung lässt man in möglichst rasehem Tempo zu einer eiskalten Lösung von 32 Teilen l.-Oxynaphtha:lin-4,8-disulfonsäure und 30 Teilen wasserfreiere Natriurnea.rbonat in 450 Teilen Wasser fliessen.
Nach etwa 15 Minuten hat die Bildung der Diazoazov erbin- dung stattgefunden, worauf man eine eiskalte Lösung von 40 Teilen 2-(4'-Carboxymethoxy- phenyl) -amino- 5-oxynaphthalin-7-sulfonsäure und 10 Teilen wasserfreiem Natriumearbonat in 300 Teilen Wasser zufliessen lässt. Nach einigen Stunden erwärmt man die Suspension des entstehenden Disazofarbstoffes auf 60 , gibt etwa 150 Teile Natriumehlorid zu und filtriert den nun ausgefällten Farbstoff ab.
Eine bei 80 hergestellte Lösung dieser Farbstoffpaste in 2000 Teilen Wasser wird mit 52 Teilen Kupfersulfat und 200 Teilen konzentriertem Ammoniak versetzt und einige Stunden bei 90 bis 100 gerührt, wobei die Kupferung unter Bildung der o,o'-Dioxyazo- komplexe erfolgt. Man scheidet den kupfer haltigen Farbstoff durch Zugabe von 200 Teilen Natriumchlorid ab, filtriert und trocknet.
Vorteilhaft kann die Kupferun,- auch mit Kupferacetat bzw. einer Mischung von Kupfersulfat und Natriumacetat durchge führt werden, z. B. indem man das Reaktions gemisch oder den primär entstandenen Kom plex trocknet und einige Stunden auf etwa 125 erwärmt.
<B> Process for the production of a copper-containing </B> disazo carbate. 1: It has been found that a valuable, copper-containing disazo dye is obtained by using a disazo dye of the formula
EMI0001.0005
lets copper-donating agents act under such conditions that splitting of the --0-alkyl groups takes place with the formation of the bis- (o, o '- (lioxyazokupferkoinplexes).
The new dye forms a dark powder that dissolves in water with a no-blue color, and cotton made from sodium sulphate in a bath in pure blue shades of high lightfastness. colors.
The disazo dyes used in the present process as starting materials of the above formula, which are expediently used in the form of a 4lkali salt, can be obtained by adding a tetrazotized 3,3'-dialkoxy -4,4'-diaminodiphenyl, preferably tetrazotized 3 , 3'-Dimet.roxv-4,4'-di-aminodiphenyl on the one hand with l.-oxynaphthalene-4,
8-distlfonic acid and on the other hand with 2- (4'- ('arboxyniethoxyphenpl.) - amino - 5 - oxynaphthaliri-7-stilfonsätire. The order of coupling is arbitrary.
Treatment with copper-releasing agents is carried out in the same way. that the bis (o, o'-dioxyazo copper complex) is formed with splitting of the -0-alkyl groups. Methods which lead to such a complete copper plating are generally known. Has proven particularly successful z.
B. the method according to which coppering is carried out for one to several hours in the vicinity of 100 in an aqueous medium using copper tetrammine complexes in the presence or absence of excess ammonia.
The copper plating can, however, also be carried out with copper acetate or a mixture of copper sulphate and N sodium acetate. by adding the reaction mixture or the primary copper complex in which the alkoxy groups have not yet been split up, a few hours in dry. Condition treated at temperatures over 100 ..
<I> Example: </I> 24.1 parts of dianisidine are suspended in 300 parts of water and 50 parts of 301.10% hydrochloric acid and tetrazotized at 0 to 2 with 14 parts of sodium nitrite. The clear solution of the tetrazo compound is allowed to flow as rapidly as possible into an ice-cold solution of 32 parts of 1.-oxynaphtha: lin-4,8-disulfonic acid and 30 parts of anhydrous sodium carbonate in 450 parts of water.
After about 15 minutes, the formation of the diazoazov 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 is added Allows water to flow in. After a few hours, the suspension of the disazo dye formed is heated to 60, about 150 parts of sodium chloride are added and the dye which has now precipitated is filtered off.
A solution of this dye paste prepared at 80 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 taking place with formation of the o, o'-dioxyazo complexes. The copper-containing dye is separated off by adding 200 parts of sodium chloride, filtered and dried.
Advantageously, the Kupferun, - also with copper acetate or a mixture of copper sulfate and sodium acetate Runaway leads, for. B. by drying the reaction mixture or the primarily resulting complex complex and heated to about 125 hours.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH277658T | 1949-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH277658A true CH277658A (en) | 1951-09-15 |
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 After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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. |
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 |
|---|---|
| CH280732A (en) | 1952-01-31 |
| GB674707A (en) | 1952-06-25 |
| FR1023892A (en) | 1953-03-25 |
| DE889662C (en) | 1953-09-14 |
| CH280731A (en) | 1952-01-31 |
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