DE1054195B - Process for coloring lacquers containing esters as solvent - Google Patents
Process for coloring lacquers containing esters as solventInfo
- Publication number
- DE1054195B DE1054195B DEB31129A DEB0031129A DE1054195B DE 1054195 B DE1054195 B DE 1054195B DE B31129 A DEB31129 A DE B31129A DE B0031129 A DEB0031129 A DE B0031129A DE 1054195 B DE1054195 B DE 1054195B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- solvent
- chromium
- oxy
- containing esters
- 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
- 150000002148 esters Chemical class 0.000 title claims description 8
- 239000004922 lacquer Substances 0.000 title claims description 8
- 239000002904 solvent Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000004040 coloring Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- -1 ether alcohols Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000011651 chromium Substances 0.000 claims description 3
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical class [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000004780 naphthols Chemical class 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 7
- 239000002966 varnish Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 2
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 235000007831 chromium(III) chloride Nutrition 0.000 description 2
- 239000011636 chromium(III) chloride Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
Description
Verfahren zum Färben von Ester als Lösungsmittel enthaltenden Lacken Es wurde gefunden, daß man Ester als Lösungsmittel enthaltende Lacke in besonders vorteilhafter Weise färben kann, wenn man durch Erhitzen aromatischer o-Oxyaldehyde der allgemeinen Formel in der R ein Halogenatom oder eine Alkyl- oder Nitrogruppe und R' ein Wasserstoff- oder Halogenatom oder eine Alkyl- oder Nitrogruppe ist oder R und R' gemeinsam einen der Aldehydgruppe benachbarten zweiten Benzolring bilden, in Gegenwart von mehrwertigen Alkoholen oder von Ätheralkoholen und zweckmäßig ohne Zusatz von Wasser mit sulfonsäuregruppenfreien o-Aminophenolen oder -naphtholen und mit mindestens einem Äquivalent eines Chrom(III)-salzes auf etwa 100 bis 140° C erhaltene chromhaltige Azomethinfarbstoffe verwendet.Process for coloring lacquers containing esters as solvents It has been found that lacquers containing esters as solvents can be colored in a particularly advantageous manner if aromatic o-oxyaldehydes of the general formula are heated by heating in which R is a halogen atom or an alkyl or nitro group and R 'is a hydrogen or halogen atom or an alkyl or nitro group or R and R' together form a second benzene ring adjacent to the aldehyde group, in the presence of polyhydric alcohols or of ether alcohols and expediently chromium-containing azomethine dyes obtained without adding water with sulfonic acid group-free o-aminophenols or naphthols and with at least one equivalent of a chromium (III) salt at about 100 to 140 ° C.
Zur hier nicht beanspruchten Herstellung der erfindungsgemäß zu verwendenden Farbstoffe geeignete aromatische o-Oxyaldehyde sind z. B. der 2-Oxy-3,5-dichlorbenzaldehyd, der 4- oder 5-Nitro-2-oxybenzaldebyd, der 3-Nitro-4-methyl-6-oxybenzaldehyd, der 5-Chlor-4-methyl-2-oxybenzaldehyd, der 2-Oxy-1-naphthaldehyd oder der 2-Oxy-5-tert.-butylbenzaldehyd.For the production, which is not claimed here, to be used according to the invention Dyes suitable aromatic o-oxyaldehydes are z. B. the 2-oxy-3,5-dichlorobenzaldehyde, the 4- or 5-nitro-2-oxybenzaldehyde, the 3-nitro-4-methyl-6-oxybenzaldehyde, the 5-chloro-4-methyl-2-oxybenzaldehyde, 2-oxy-1-naphthaldehyde or 2-oxy-5-tert.-butylbenzaldehyde.
Als o-Aminophenole und -naphthole eignen sich zur Herstellung der Farbstoffe außer dem unsubstituierten o-Aminophenol und dem 1-Am.ino-2-oxy- oder 2-Amino-l-oxynaphthalin z. B. das 4- oder 5-Nitro-2-aminoph-etiol.As o-aminophenols and naphthols are suitable for the production of Dyes except for the unsubstituted o-aminophenol and the 1-Am.ino-2-oxy- or 2-amino-1-oxynaphthalene e.g. B. the 4- or 5-nitro-2-aminoph-etiol.
Geeignete Chrom(III)-salze sind z. B. das Chrom(III)-chlorid oder Lösungen von Chromoxyd in Salzsäure oder Ameisensäure.Suitable chromium (III) salts are, for. B. the chromium (III) chloride or Solutions of chromium oxide in hydrochloric acid or formic acid.
Als Alkohole bzw. Ätheralkohole eignen sich für die Herstellung der Farbstoffe unter anderem Glycerin, Butantriol, die Butandiole und vor allem das Äthylenglykol und seine Monoalkyläther, der ß,ß'-Dioxydiäthyläther und die höheren Einwirkungsprodukte von Äthylenoxyd auf Äthylenglykol.As alcohols or ether alcohols are suitable for the production of Dyes including glycerine, butanetriol, butanediols and above all that Ethylene glycol and its monoalkyl ethers, the ß, ß'-Dioxydiethyläther and the higher Products of the action of ethylene oxide on ethylene glycol.
Aus der französischen Patentschrift 811814 sind Schwermetallkomplexverbindungen von Azomethinfarbstoffen bekannt, die man durch Erhitzen von aromatischen o-Oxyaminen mit o-Oxycarbonylverbindungen und Schwermetallsalzen in organischen Lösungsmitteln, wie Äthanol, erhält. Die dort beschriebenen Azometh.in-Metall-Komplexfarbstoffe sind in organischen Lösungsmitteln außer Pyridin unlöslich; sie sind also nur als Pigmente verwendbar. Demgegenüber erhält man mit den erfindungsgemäß zu verwendenden Farbstoffen, die in organischen Lösungsmitteln, insbesondere in Estern, gut löslich sind, klare transparente Lacke.Heavy metal complex compounds of azomethine dyes are known from French patent 811 814, which are obtained by heating aromatic o-oxyamines with o-oxycarbonyl compounds and heavy metal salts in organic solvents such as ethanol. The azometh.in metal complex dyes described there are insoluble in organic solvents except for pyridine; so they can only be used as pigments. In contrast, the dyes to be used according to the invention which are readily soluble in organic solvents, in particular in esters, give clear, transparent lacquers.
Die in den Beispielen genannten Teile sind Gewichtsteile.The parts mentioned in the examples are parts by weight.
Beispiel 1 In 1 1 eines Esters als Lösungsmittel enthaltenden Lacks, der aus 7% Nitrocellulose, 3% Dibutylphthalat, 2% Colophonium, 65% Äthylacetat, 131/o Butylacetat und 10% Butanol besteht, löst man 20g eines Farbstoffes, der wie folgt hergestellt wurde: Ein Gemisch von 8 Teilen 4-Nitro-2-ami.nophenol und 10 Teilen 2-Oxy-3,5-dichlorbenzaldehyd wird in eine Lösung von 15 Teilen kristallisiertem Chromchlorid (CrCl3, 6 H,0) in 150 Teilen Äthylenglykol eingerührt. Die Mischung wird unter Rühren auf 125 bis 130° C erhitzt und so lange bei dieser Temperatur gehalten, bis man eine einheitliche gelbe Lösung erhält, was etwa 3 Stunden dauert. Dann gießt man die Lösung in 1 1 Wasser, fügt 15 Teile kristallisiertes Natriumacetat zu, rührt noch 1 Stunde nach, saugt den Farbstoff ab, wäscht ihn mit Wasser und trocknet ihn bei 70 bis 80° C. Man erhält einen klaren gelben Lack, der sehr lichtechte Aufstriche oder Lackierungen ergibt.Example 1 In 1 1 of a lacquer containing ester as a solvent, the one made from 7% nitrocellulose, 3% dibutyl phthalate, 2% rosin, 65% ethyl acetate, 131 / o butyl acetate and 10% butanol, you dissolve 20g of a dye which as was prepared as follows: A mixture of 8 parts of 4-nitro-2-ami.nophenol and 10 Parts of 2-oxy-3,5-dichlorobenzaldehyde is crystallized in a solution of 15 parts Chromium chloride (CrCl3, 6 H, 0) stirred into 150 parts of ethylene glycol. The mixture is heated with stirring to 125 to 130 ° C and so long at this temperature held until a uniform yellow solution is obtained, which takes about 3 hours. The solution is then poured into 1 l of water, and 15 parts of crystallized sodium acetate are added to, stir for 1 hour, sucks off the dye, washes it with water and dries it at 70 to 80 ° C. A clear yellow varnish is obtained which is very lightfast Spreads or varnishes results.
Nimmt man zur Herstellung des Farbstoffes an Stelle von 2-Oxy-3,5-dichlorbenzaldehyd 8,5 Teile 2-Oxy-5-nitrobenzaldehyd, so erhält man einen gelben Lack mit ähnlichen Eigenschaften.If you use 2-oxy-3,5-dichlorobenzaldehyde instead of 2-oxy-3,5-dichlorobenzaldehyde for the preparation of the dye 8.5 parts of 2-oxy-5-nitrobenzaldehyde, this gives a yellow paint with similar properties Properties.
Beispiel 2 Man färbt einen Ester als Lösungsmittel enthaltenden Lack von ähnlicher Zusammensetzung wie im Beispiel 1 mit 1 bis 2% eines Farbstoffes, der wie folgt hergestellt wurde: 100 Teile ß,ß'-Dioxyäthyläther werden mit 4 Teilen Chromoxyd (Cr20s) und 10 Teilen einer Salzsäure vom spezifischen Gewicht 1,16 versetzt. Man erwärmt das Gemisch auf 120 bis 130° C, trägt nach einer halben Stunde bei der gleichen Temperatur ein Gemisch von 7,5 Teilen 5-Nitro-2-aminophenol und 10 Teilen 2-Oxy-3,5-dichlorbenzaldehyd ein und rührt weitere 3 Stunden bei 130° C. Dann gießt man die entstandene gelborange Lösung in 1 1 Wasser, fügt 15 Teile kristallisiertes Natriumacetat hinzu, rührt 1 Stunde nach, saugt den Farbstoff ab, wäscht ihn mit Wasser nach und trocknet ihn bei 80° C. Man erhält einen klaren orangefarbenen Lack, der klare lichtechte Lackierungen ergibt.Example 2 A varnish containing ester as a solvent is colored of a composition similar to that in Example 1 with 1 to 2% of a dye, which was made as follows: 100 parts of ß, ß'-dioxyethyl ether are mixed with 4 parts of chromium oxide (Cr20s) and 10 parts of a hydrochloric acid of the specific Weight 1.16 offset. The mixture is heated to 120 to 130 ° C, carries after a half an hour at the same temperature a mixture of 7.5 parts of 5-nitro-2-aminophenol and 10 parts of 2-oxy-3,5-dichlorobenzaldehyde and stirred for a further 3 hours at 130 ° C. The resulting yellow-orange solution is then poured into 1 liter of water and 15 parts are added crystallized sodium acetate added, stirred for 1 hour, sucks off the dye, washes it with water and dries it at 80 ° C. A clear orange color is obtained Lacquer that produces clear, lightfast lacquers.
Nimmt man zur Herstellung des Farbstoffes statt 2-Oxy-3,5-dichlorbenzaldehyd 9 Teile 2-Oxy-5- tert.-butyibenzaldehyd, so erhält man einen ähnlich guten Lack. Beispiel 3 Man färbt einen Ester als Lösungsmittel enthaltenden Lack von ähnlicher Zusammensetzung wie im Beispiel 1 mit 1 bis 2% eines Farbstoffes, der wie folgt hergestellt wurde: Ein Gemisch von 8 Teilen 4-Nitro-2-aminophenol und 8 Teilen 2-Oxy-l-naphthaldehyd wird in eine Lösung von 15 Teilen kristallisiertem Chromchlorid (Cr C13, 61120) in 150 Teilen Äthylenglykol eingetragen. Man verfährt dann weiter wie im Beispiel 1 und erhält-auf-diese Weise einen orangebraunen Lack, der gut lichtechte, klare Aufstriche ergibt.If, instead of 2-oxy-3,5-dichlorobenzaldehyde, 9 parts of 2-oxy-5-tert-butyibenzaldehyde are used to prepare the dye, a similarly good varnish is obtained. EXAMPLE 3 A varnish containing ester as a solvent and having a composition similar to that in Example 1 is colored with 1 to 2% of a dye which was prepared as follows: A mixture of 8 parts of 4-nitro-2-aminophenol and 8 parts of 2-oxy- 1-naphthaldehyde is introduced into a solution of 15 parts of crystallized chromium chloride (Cr C13, 61120) in 150 parts of ethylene glycol. The procedure then continues as in Example 1 and in this way an orange-brown varnish is obtained which gives clear, light-fast spreads.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB31129A DE1054195B (en) | 1954-05-22 | 1954-05-22 | Process for coloring lacquers containing esters as solvent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB31129A DE1054195B (en) | 1954-05-22 | 1954-05-22 | Process for coloring lacquers containing esters as solvent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1054195B true DE1054195B (en) | 1959-04-02 |
Family
ID=6963411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB31129A Pending DE1054195B (en) | 1954-05-22 | 1954-05-22 | Process for coloring lacquers containing esters as solvent |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1054195B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR811814A (en) * | 1935-10-12 | 1937-04-23 | Ig Farbenindustrie Ag | Metal dyes and their production process |
-
1954
- 1954-05-22 DE DEB31129A patent/DE1054195B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR811814A (en) * | 1935-10-12 | 1937-04-23 | Ig Farbenindustrie Ag | Metal dyes and their production process |
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