DE1150769B - Process for the production of azo dyes - Google Patents
Process for the production of azo dyesInfo
- Publication number
- DE1150769B DE1150769B DEF31483A DEF0031483A DE1150769B DE 1150769 B DE1150769 B DE 1150769B DE F31483 A DEF31483 A DE F31483A DE F0031483 A DEF0031483 A DE F0031483A DE 1150769 B DE1150769 B DE 1150769B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- azo
- dyes
- azo dyes
- 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
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 acyl acetic acid Chemical compound 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WJFFMVZCPGZKGJ-UHFFFAOYSA-N 2-[(3-amino-4-methoxyphenyl)sulfonylamino]ethyl hydrogen sulfate Chemical compound S(=O)(=O)(OCCNS(=O)(=O)C1=CC(=C(C=C1)OC)N)O WJFFMVZCPGZKGJ-UHFFFAOYSA-N 0.000 description 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PBTYYPVUCDUKST-UHFFFAOYSA-N NC=1C=C(C=CC=1C)S(=O)(=O)NCCOS(O)(=O)=O Chemical compound NC=1C=C(C=CC=1C)S(=O)(=O)NCCOS(O)(=O)=O PBTYYPVUCDUKST-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride 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
- 210000003298 dental enamel Anatomy 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001052 yellow pigment 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
- C09B63/00—Lakes
- C09B63/005—Metal lakes of dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Azofarbstoffen Es wurde gefunden, daß man wertvolle Azo-Pigmentfarbstoffe erhält, wenn man diazotierte Amine der allgemeinen Formel worin X Wasserstoff, Halogen, Alkyl oder Alkoxydarstellt, mit von nicht verlackbaren Sulfonsäure- und Carbonsäuregruppen freien Azokomponenten vereinigt und anschließend mit Salzen zweiwertiger Metalle, insbesondere des Bariums und des Calciums, verlackt.Process for the preparation of azo dyes It has been found that valuable azo pigment dyes are obtained if diazotized amines of the general formula are used wherein X represents hydrogen, halogen, alkyl or alkoxide, combined with azo components free of non-lacquerable sulfonic acid and carboxylic acid groups and then lacquered with salts of divalent metals, in particular of barium and calcium.
Als Azokomponenten lassen sich beispielsweise verwenden Arylamide der 2,3-Hydroxynaphthalincarbonsäure, 1-Aryl-3-methyl-5-pyrazolone oder Acylessigsäurearylamide, die mit Ausnahme von nicht verlackbaren Sulfonsäure- und Carbonsäuregruppen in Azofarbstoffen übliche Substituenten aufweisen können. Verlackbar sind solche Sulfonsäure- und Carbonsäuregruppen, die bei Einwirkung von Salzen vornehmlich zweiwertiger Metalle, z. B. des Bariums, Calciums, Magnesiums, Mangans, unter Verlust der löslichmachenden Wirkung in einen sogenannten Lack übergeführt werden. Dies ist, um nur wenige Beispiele zu nennen, bei der 2,3-Hydroxynaphthoesäure und der 2-Hydroxynaphthalin-3,6-disulfonsäure der Fall.Arylamides, for example, can be used as azo components 2,3-hydroxynaphthoic acid, 1-aryl-3-methyl-5-pyrazolone or acyl acetic acid arylamides, those with the exception of non-lacquerable sulfonic acid and carboxylic acid groups in azo dyes can have customary substituents. Such sulfonic acid and Carboxylic acid groups which, when exposed to salts, are mainly divalent metals, z. B. of barium, calcium, magnesium, manganese, with loss of the solubilizing Effect can be converted into a so-called varnish. This is to give just a few examples to mention, in the case of 2,3-hydroxynaphthoic acid and 2-hydroxynaphthalene-3,6-disulfonic acid the case.
Die neuen Farbstoffe sind in Wasser und den üblichen organischen Lösungsmitteln unlöslich; sie zeichnen sich durch hervorragende Überlackierechtheit in Nitroalkydharz- oder Einbrennlacken sowie durch gute Lichtechtheit aus und sind daher in besonderer Weise zur Färbung von Lacken und Papier geeignet.The new dyes are in water and the usual organic solvents insoluble; they are characterized by excellent fastness to overcoating in nitroalkyd resin or stoving enamels as well as good lightfastness and are therefore special Suitable for coloring paints and paper.
In den folgenden Beispielen verhalten sich Gewichtsteile zu Volumteilen wie Gramm zu Millilitern. Beispiel 1 a) 32,6 Gewichtsteile 1-Methoxy-2-aminobenzol-4-sulfonylaminoäthylhydrogensulfat werden mit 600 Volumteilen Wasser und 28 Volumteilen Salzsäure (19,5° B6) fein verrührt und bei 0 bis 5°C mit 23 Volumteilen 30°/oiger Natriumnitritlösung diazotiert. Zu der geklärten Diazolösung werden 25 Volumteile Eisessig und anschließend eine wäßrige Lösung des Natriumsalzes von 33 Gewichtsteilen 1-(2',3'-Hydroxynaphthoylamino)-4-methoxybenzol gegeben. Nach beendeter Kupplung werden 20 Gewichtsteile kristallisiertes Bariumchlorid zugegeben, 2 Stunden auf 90°C erhitzt, abgesaugt, gewaschen und bei 50 bis 60°C getrocknet.In the following examples, parts by weight are related to parts by volume like grams to milliliters. Example 1 a) 32.6 parts by weight of 1-methoxy-2-aminobenzene-4-sulfonylaminoethyl hydrogen sulfate are finely mixed with 600 parts by volume of water and 28 parts by volume of hydrochloric acid (19.5 ° B6) and diazotized at 0 to 5 ° C with 23 parts by volume of 30% sodium nitrite solution. to the clarified diazo solution is 25 parts by volume of glacial acetic acid and then an aqueous one Solution of the sodium salt of 33 parts by weight of 1- (2 ', 3'-hydroxynaphthoylamino) -4-methoxybenzene given. After the coupling has ended, 20 parts by weight of crystallized barium chloride are obtained added, heated to 90 ° C for 2 hours, filtered off with suction, washed and at 50 to 60 ° C dried.
3 Gewichtsteile des so erhaltenen Pigmentfarbstoffes werden in 100 Gewichtsteilen eines Nitroalkydharzlackes (mit einem Festkörpergehalt von 22 °/o) in einer Trichtermühle angerieben. Mit dem auf Spritzviskosität eingestellten Lack lassen sich rote Lackierungen mit sehr guter Überlackierechtheit herstellen.3 parts by weight of the pigment dye thus obtained are in 100 Parts by weight of a nitroalkyd resin lacquer (with a solids content of 22%) ground in a funnel grinder. With the paint adjusted to the spray viscosity red lacquers can be produced with very good fastness to overcoating.
b) Ersetzt man in diesem Beispiel die Azokomponente durch 17,5 Gewichtsteile 1-Phenyl-3-methyl-5-pyrazolon, so erhält man einen gelben Pigmentlack, der hervorragend zur Herstellung lösungsmittelechter graphischer Drucke und zur Bereitung von überspritzechten Farblacken geeignet ist.b) In this example, the azo component is replaced by 17.5 parts by weight 1-phenyl-3-methyl-5-pyrazolone, a yellow pigment varnish is obtained that is excellent for the production of solvent-resistant graphic prints and for the preparation of overmolded ones Color lacquers is suitable.
Beispiel 2 31,0 Gewichtsteile 1-Methyl-2-aminobenzol-4-sulfonylaminoäthylhydrogensulfat werden analog Beispiel 1 diazotiert und mit der wäßrigen Lösung des Natriumsalzes von 35 Gewichtsteilen 1-(2',3'-Hydroxynaphtholyamino)-4-äthoxybenzol gekuppelt. Anschließend wird der Farbstoff mit 20 Gewichtsteilen kristallisiertem Bariumchlorid oder mit 18 Gewichtsteilen Calciumchlorid verlackt. Die verlackten Farbstoffe besitzen ähnliche Eigenschaften wie der Pigmentfarbstoff des Beispiels 1,a).Example 2 31.0 parts by weight of 1-methyl-2-aminobenzene-4-sulfonylaminoethyl hydrogen sulfate are diazotized analogously to Example 1 and with the aqueous solution of the sodium salt coupled by 35 parts by weight of 1- (2 ', 3'-hydroxynaphtholyamino) -4-ethoxybenzene. The dye is then mixed with 20 parts by weight of crystallized barium chloride or lacquered with 18 parts by weight of calcium chloride. Own the laked dyes properties similar to those of the pigment of Example 1, a).
In ähnlicher Weise werden mit den in der folgenden Tabelle angeführten
Diazo- und Azokomponenten Pigmentlacke des Bariums oder des Calciums erhalten, die
Lacke und Papier in den angegebenen Farbtönen licht- und lösungsmittelecht färben.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31483A DE1150769B (en) | 1960-06-22 | 1960-06-22 | Process for the production of azo dyes |
| BE604365A BE604365A (en) | 1960-06-22 | 1961-05-30 | Azo dyes, their preparation process and their application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31483A DE1150769B (en) | 1960-06-22 | 1960-06-22 | Process for the production of azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1150769B true DE1150769B (en) | 1963-06-27 |
Family
ID=7094218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31483A Pending DE1150769B (en) | 1960-06-22 | 1960-06-22 | Process for the production of azo dyes |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE604365A (en) |
| DE (1) | DE1150769B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2239814A1 (en) * | 1972-08-12 | 1974-02-21 | Bayer Ag | MONOAZO DYES |
-
1960
- 1960-06-22 DE DEF31483A patent/DE1150769B/en active Pending
-
1961
- 1961-05-30 BE BE604365A patent/BE604365A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2239814A1 (en) * | 1972-08-12 | 1974-02-21 | Bayer Ag | MONOAZO DYES |
| US4055557A (en) * | 1972-08-12 | 1977-10-25 | Bayer Aktiengesellschaft | Sulfonamidobenzene-azo-aminopyrazole dyestuffs |
Also Published As
| Publication number | Publication date |
|---|---|
| BE604365A (en) | 1961-09-18 |
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