DE479373C - Process for the preparation of metal compounds of dyes - Google Patents
Process for the preparation of metal compounds of dyesInfo
- Publication number
- DE479373C DE479373C DEI28322D DEI0028322D DE479373C DE 479373 C DE479373 C DE 479373C DE I28322 D DEI28322 D DE I28322D DE I0028322 D DEI0028322 D DE I0028322D DE 479373 C DE479373 C DE 479373C
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- metal compounds
- preparation
- parts
- weight
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 14
- 150000002736 metal compounds Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- -1 butyl alcohols Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- DNHVXYDGZKWYNU-UHFFFAOYSA-N lead;hydrate Chemical compound O.[Pb] DNHVXYDGZKWYNU-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 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
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Metallverbindungen von Farbstoffen Behandelt man in Wasser schwer- oder unlösliche Farbstoffe, die zur Bildung komplexer Metallverbindungen befähigt sind, mit wäßrigen Lösungen von Metallverbindungen, so entstehen die komplexen. Metallverbindun; gen der Farbstoffe nicht oder nur sehr unvollständig.Process for the preparation of metal compounds treated by dyes dyes that are sparingly soluble or insoluble in water lead to the formation of complex metal compounds are able to work with aqueous solutions of metal compounds, so the complex arises. Metal connection; gen of the dyes not or only very incompletely.
Auch die bekannte Chromierung mit stark alkalischen komplexen Chromitlösungen, die durch Einwirkung von, alkalischen Chromoxydsuspensionen auf organische Hydroxylverbindungen erst hergestellt werden müssen., führen nicht immer zum Ziele, besonders dann nicht, wenn man in saurem Medium arbeiten muß.Also the well-known chroming with strongly alkaline complex chromite solutions, those caused by the action of, alkaline chromium oxide suspensions on organic hydroxyl compounds first have to be produced., do not always lead to the goal, especially not then, if you have to work in an acidic medium.
Es wurde nun gefunden, daß sich die komplexen Metallverbindungen der Farbstoffe sehr glatt -und vollständig bilden, wenn man die Einwirkung in Gegenwart von geeigneten organischen Lösungsmitteln, zweckmäßig solchen, die unter den angewandten Bedingungen in Wasser wenigstens teilweise löslich sind und die Farbstoffe oder deren Metallverb.indungen zu lösen vermögen, erfolgen läßt. Im übrigen kann die Einwirkung der Metallverbindungen auf die Farbstoffe in beliebiger Weise, z. B. mit oder ohne Anwendung von Druck usw., erfolgen. Als, geeignete Lösungsmittel seien beispielsweise genannt ein- oder mehrwertige Alkohole, wie, Methyl-, Äthyl-, Propyl-, Butylalkohole usw., Glykol und dessen Äther oder Ester, Polyglykol, Glycerin, ferner Äthylenchlorhydrin, Triäthanolamin, Thiodiglykol, Phenole, Aceton und andere Ketone usw. Auch Gemische von organischen Lösungsmitteln sind verwendbar. Beispiel i 28 Gewichtsteile des Azofarbstoffs aus der Diazoverbindung von p-Clilor-o-aminophenol und ß-Naphthol werden mit etwa ¢0o Volumteilen Äthylalkohol und 12o Gewichtsteilen einer wäßrigen Lösung, die 7,6 Gewichtsteile Chromoxyd und 13,5 Gewichtsteile Ameisensäure (85prozentig) enthält, etwa Stunden bei 12o° im Autoklaven erhitzt. Der erhaltene, teilweise gelöste Farbstoff wird durch Zugabe von Wasser oder durch Abdestillieren des Alkohols gefällt, abgesaugt und gewaschen. Man erhält nach dem Trocknen einen violetten Farbatoff, der in alkoholischer Lösung mit Alkali nicht mehr umschlägt. Versucht man die gleichen chromhaltigen Farbstoffe in Wasser unter sonst gleichen Bedingungen darzustellen, so bleibt ein großer Teil des Ausgangsfarbstoffes unverändert.It has now been found that the complex metal compounds of the dyes form very smoothly and completely when the action is taken in the presence of suitable organic solvents, expediently those which are at least partially soluble in water under the conditions used and the dyes or their metal compounds . Able to resolve ties, can take place. In addition, the action of the metal compounds on the dyes in any way, for. B. with or without the application of pressure, etc., take place. Suitable solvents are, for example, mono- or polyhydric alcohols such as methyl, ethyl, propyl, butyl alcohols, etc., glycol and its ethers or esters, polyglycol, glycerol, and also ethylene chlorohydrin, triethanolamine, thiodiglycol, phenols, acetone and other ketones, etc. Mixtures of organic solvents can also be used. Example i 28 parts by weight of the azo dye from the diazo compound of p-Clilor-o-aminophenol and ß-naphthol are mixed with about ¢ 0o parts by volume of ethyl alcohol and 12o parts by weight of an aqueous solution containing 7.6 parts by weight of chromium oxide and 13.5 parts by weight of formic acid (85 percent) contains, heated for about hours at 12o ° in the autoclave. The partially dissolved dye obtained is precipitated by adding water or by distilling off the alcohol, filtered off with suction and washed. After drying, a violet dye is obtained which no longer changes in alcoholic solution with alkali. If one tries to produce the same chromium-containing dyes in water under otherwise identical conditions, a large part of the starting dye remains unchanged.
In analoger Weise läßt sich mit Kupferformiat die entsprechende Kupferverbindung darstellen. An Stelle von Äthylalkohol ist auch Aceton verwendbar.The corresponding copper compound can be prepared in an analogous manner with copper formate represent. Acetone can also be used instead of ethyl alcohol.
Beispiel 2 32 Gewichtsteile des Azofarbstoffs aus der Diazoverbindung von p-Chlor-o-aminophenol und 3-Methyl-i-phenyl-5-pyrazolon werden mit ¢0o Volumteilen Äthylalkohol und der gleichen Chromformatlösung, wie in Beispiel i angegeben; etwa 3 bis q. Stunden im Autoklaven aufs i2o° erhitzt. Durch Zusatz von Wasser zurr Reaktionsgemisch erhält man die rote Chromverbindung des Farbstoffs. An Stelle des Äthylalkohols kann bei der Darstellung z. B. auch ein Gemisch aus Methyl- und Benzylalkohol verwendet werden.Example 2 32 parts by weight of the azo dye from the diazo compound of p-chloro-o-aminophenol and 3-methyl-i-phenyl-5-pyrazolone are ¢ 0o parts by volume Ethyl alcohol and the same chromium format solution as given in example i; approximately 3 to q. Hours in the autoclave heated to i2o °. By adding water to the reaction mixture the red chromium compound of the dye is obtained. Instead of ethyl alcohol can be used in the representation z. B. also used a mixture of methyl and benzyl alcohol will.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI28322D DE479373C (en) | 1926-06-15 | 1926-06-16 | Process for the preparation of metal compounds of dyes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE272908X | 1926-06-15 | ||
| DEI28322D DE479373C (en) | 1926-06-15 | 1926-06-16 | Process for the preparation of metal compounds of dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE479373C true DE479373C (en) | 1929-07-17 |
Family
ID=25772216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI28322D Expired DE479373C (en) | 1926-06-15 | 1926-06-16 | Process for the preparation of metal compounds of dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE479373C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE743172C (en) * | 1937-02-06 | 1943-12-20 | Geigy Ag J R | Process for the production of chromium complex compounds of mordant dyes which are soluble in organic solvents containing oxy groups |
| DE931061C (en) * | 1952-10-10 | 1955-08-01 | Basf Ag | Process for the production of metal-containing azo dyes |
-
1926
- 1926-06-16 DE DEI28322D patent/DE479373C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE743172C (en) * | 1937-02-06 | 1943-12-20 | Geigy Ag J R | Process for the production of chromium complex compounds of mordant dyes which are soluble in organic solvents containing oxy groups |
| DE931061C (en) * | 1952-10-10 | 1955-08-01 | Basf Ag | Process for the production of metal-containing azo dyes |
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