DEP0035044DA - Process for the production of the same monoazo dyes. - Google Patents
Process for the production of the same monoazo dyes.Info
- Publication number
- DEP0035044DA DEP0035044DA DEP0035044DA DE P0035044D A DEP0035044D A DE P0035044DA DE P0035044D A DEP0035044D A DE P0035044DA
- Authority
- DE
- Germany
- Prior art keywords
- production
- monoazo dyes
- yellow
- dyes
- same
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 title description 8
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical class C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- DWOBGCPUQNFAFB-UHFFFAOYSA-N 2-benzylaniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1 DWOBGCPUQNFAFB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- NNZXDXMEXBYSRF-UHFFFAOYSA-N 2-methyl-4H-pyrazol-3-one Chemical compound CN1N=CCC1=O NNZXDXMEXBYSRF-UHFFFAOYSA-N 0.000 description 1
- WDTRNCFZFQIWLM-UHFFFAOYSA-N 4-benzylaniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1 WDTRNCFZFQIWLM-UHFFFAOYSA-N 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Stearin Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Description
Es wurde gefunden, dass man wertvolle neue wasserunlöe* liehe gelbe Monoazofarbstoffe erhält, wenn man die Diazoverbinduiög) von Aminodiphenylmethanen mit einer Gelbkomponente, die keine Carboxyl- oder SuIfonsäuregruppe enthält, eg^ /nft-i/ψ et/. It has been found that valuable new water-insoluble yellow monoazo dyes are obtained if the diazo compounds are obtained from aminodiphenylmethanes with a yellow component which contains no carboxyl or sulfonic acid group, eg ^ / nft-i / ψ et /.
Diese Farbstoffe sind in Wasser unlöslich, aber in organischen Lösungsmitteln gut löslich» Sie lassen sich zum Färben von Kohlenwasserstoffen, Kerzen, Lacken und zur Herstellung von Druck* farben verwenden. Da die bei letzterer Verwendungsart erhaltenen Buntdrucke eine beachtliche Sublimierechtheit aufweisen, sind die Farbstoffe vorliegender Erfindung besonders für den Doppeltondruck geeignet.These dyes are insoluble in water, but easily soluble in organic solvents. »They can be used for coloring Use hydrocarbons, candles, lacquers and for the production of printing inks. Since the obtained with the latter type of use Colored prints have a remarkable fastness to sublimation, the dyes of the present invention are particularly suitable for double-tone printing suitable.
19,7 kg 2-Aminodiphenylmethan werden mit überschüssiger Salzsäure in Lösung gebracht. Nach dem Abkühlen auf 0° wird in üblicher Weise mit Natriumnitrit diazotiert. Die Diazolöeung wird mit einer sodaalkalischen Lösung von 17,5 kg 1-Phenyl =»3 methyl 5-pyrazölon vereinigt. Der Farbstoff, der sich sofort gebil» det hat, wird abfiltriert und getrocknet. Er stellt ein gelbes wasserunlösliches Pulver dar, welches sich in organischen Lösungs* mitteln mit grffnstichig gelber Farbe lost.19.7 kg of 2-aminodiphenylmethane are brought into solution with excess hydrochloric acid. After cooling to 0 °, the in Usually diazotized with sodium nitrite. The Diazolöeung is with a soda-alkaline solution of 17.5 kg of 1-phenyl = »3 methyl 5-pyrazolone combined. The dye, which has formed immediately, is filtered off and dried. It is a yellow, water-insoluble powder that dissolves in organic solutions * medium with a green-tinged yellow color.
Der Farbstoff färbt Stearin oder Paraffin in grün3tichifc gelben Farbtönen. Die Färbungen besitzen eine gute Sublimiereeht* heit, sodass der Farbstoff für den sogenannten Doppeltondrägjk geeignet ist.The dye colors stearin or paraffin in grün3tichi fc yellow hues. The dyeings have good sublimation fastness, so that the dye is suitable for the so-called double tone slip.
Andere gelbe Farbstoffe von ähnlichen Eigenschaften t*r* hält man, wenn man das 1-Phenyl-3 methyl 5-pyrazolon durch iqui* valente Mengen von anderen Pyrazolonen, Z0B0 Other yellow dyes with similar properties are obtained if 1-phenyl-3-methyl-5-pyrazolone is replaced by equivalent amounts of other pyrazolones, Z 0 B 0
1(2·1 (2
1(3 *-Chlorphenyl) ^3%4nethy 1^5~ pyraaolon,1 (3 * -chlorophenyl) ^ 3% 4nethy 1 ^ 5 ~ pyraaolon,
1(2*. ö'^Dichlorphenyl )^31 (2 *. Ö '^ dichlorophenyl) ^ 3
ersetzt, v£_replaced, v £ _
Werden als Hhtppi linger omponeat en verwendet, so erhält man gleichfalls griinstiehig gelb färbende Produkte, während mit N^Dimethylaailin ^In etwas rotstichigert Äelblvon ähnlichen Eigenschaften gewonnen! wird.If components are used as components, greenish yellow ones are also obtained Products while with N ^ Dimethylaailin ^ In something reddish-tinged Äelbl obtained from similar properties! will.
' Anstelle von 2~Aminodiphenylmethan kann man auch z.b, 4-Jlminodiphenylmethan verwenden.'Instead of 2-aminodiphenyl methane one can also use, for example, 4-aminodiphenyl methane.
Claims (1)
Family
ID=
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