CH299710A - Process for the preparation of a water-insoluble monoazo dye. - Google Patents
Process for the preparation of a water-insoluble monoazo dye.Info
- Publication number
- CH299710A CH299710A CH299710DA CH299710A CH 299710 A CH299710 A CH 299710A CH 299710D A CH299710D A CH 299710DA CH 299710 A CH299710 A CH 299710A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- monoazo dye
- preparation
- insoluble monoazo
- dye
- Prior art date
Links
- 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 claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000047 product Substances 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000005060 rubber Substances 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZJNQRITVJGUHTL-UHFFFAOYSA-N 3-amino-n-(2,5-dichlorophenyl)-4-methoxybenzamide Chemical compound C1=C(N)C(OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl ZJNQRITVJGUHTL-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Description
Verfahren zur Herstellung eines wasserunlöslichen Monoazofarbstoffes. Es wurde gefunden, dass man zu Pigment farbstoffen gelangt, wenn man die Diazover- bindun1en aus Aminen von der allgemeinen Zusammensetzung
EMI0001.0008
worin X eine Alkyl- oder Alkoxygruppe be deutet und die Anzahl der Halogensubstituen- ten im Benzolrest a auch mehr als 1 betragen kann, mit.
2,3-Oxynaphthoesäurearyliden von der allgemeinen Zusammensetzung
EMI0001.0015
worin der Benzolrest b noch weiter durch Halogenatome substituiert sein kann, kuppelt und dabei die Komponenten so wählt, dass sie keine wasserlösliehmaehenden Gruppen, z. B. #s'ulfonsäure- oder Carbonsäuregruppen, ent- tialten.
Die neuen Farbstoffe liefern rote bis blau stichig rote Farbtöne von guten Echtheits eigenschaften. Sie eignen sieh besonders zum Färben von plastischen Massen aus hochmole kularen organischen Verbindungen, also z. B. Formaldehyd und Harnstoff-, Phenol- oder Amin-Kondensationsprodukten, Vinylverbin- dungen, Kautschuk usw. und können ausser dem zur Herstellung von öl- und lichteehten Farblacken sowie - bei Zusatz zu den Spinn- lösiuigen - zur Erzeugung spinngefärbter Acetatkiulstseide und Viskosekimstseide vor teilhaft Verwendung finden.
Gegenüber den in der deutschen Patent schrift Nr. 602064 aufgeführten Monoazofarb- stoffen ähnlicher Zusammensetzung, unter denen jedoch keine erwähnt werden, welche die für das vorliegende Verfahren wesentliche besondere Art, der Häufung von Halogen atomen im Farbstoffmolekül enthalten, zeich nen sich die neuen Farbstoffe durch eine spe zifische Wirkung aus, die darin besteht, dass sie erheblich weniger in ungefärbte Polymeri- sationsprodukte aus Vinylchlorid ausbluten als die genannten Vergleichsprodukte.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser unlöslichen Monoazofarbstoffes, welches da durch gekennzeichnet ist, dass man die Diazo- niumverbindung aus 1-Amino-2-methoxybenzol- 5-carbonsäure-(2',5'-dichlorphenyl)-amid mit 1- (2',3'-Oxynaphthoylamino) - 3,4-dichlorbenzoi kuppelt.
Beispiel: 15,6 Gewichtsteile 1-Amino-2-methoxyben- zol - 5 - earbonsäure- (2',5'- dichlorphenyl )- amid werden in der üblichen Weise diazotiert. Hier auf versetzt man die Suspension der ungelö sten Diazoniumverbindung zur Entfernung der überschüssigen Mineralsäure mit Natriumaee- tat und lässt unter sehr gutem Rühren eine Lösung von 16,6 Gewichtsteilen 1-(2',3'-OYy- riaplithoylamino)-3,4-dichlor1)
enzol in verclüii;i- t er <B>.</B> Natronlauge zulaufen. Durch allmähliehes Erwärmen auf 40 C beendet man die Kupp lung. Der gebildete Farbstoff wird abfiltriert, gut ausgewaschen und getrocknet.
Das so erhaltene Produkt stellt ein rotes Pulver dar, das insbesondere zum Färben von Kautschuk, Polyviny lchlorid oder Konden sationsprodukten aus Harnstoff und Formal dehyd oder zur Herstellung von Lacken mit einer guten Öl- und Liehteehtheit verwendet werden kann.
Process for the preparation of a water-insoluble monoazo dye. It has been found that pigment dyes are obtained if the diazo compounds from amines have the general composition
EMI0001.0008
wherein X denotes an alkyl or alkoxy group and the number of halogen substituents in the benzene radical a can also be more than 1, with.
2,3-Oxynaphthoic arylidene of the general composition
EMI0001.0015
wherein the benzene radical b can be further substituted by halogen atoms, couples and thereby selects the components so that they do not contain any water-soluble groups, e.g. B. # s'ulfonic acid or carboxylic acid groups, entialten.
The new dyes deliver red to blue tinged red colors with good fastness properties. You see particularly suitable for coloring plastic masses from hochmole kularen organic compounds, so z. B. formaldehyde and urea, phenol or amine condensation products, vinyl compounds, rubber, etc. and can also be used for the production of oil and light-emitting colored lacquers and - when added to the spinning solutions - for the production of spun-dyed acetate silk and viscose silk find partial use.
Compared to the monoazo dyes of similar composition listed in German Patent No. 602064, but none of which are mentioned which contain the particular type of concentration of halogen atoms in the dye molecule which is essential for the present process, the new dyes are distinguished have a specific effect, which consists in the fact that they bleed into undyed polymerisation products made of vinyl chloride considerably less than the mentioned comparison products.
The present patent relates to a process for the preparation of a water-insoluble monoazo dye which is characterized in that the diazonium compound is obtained from 1-amino-2-methoxybenzene-5-carboxylic acid (2 ', 5'-dichlorophenyl) amide couples with 1- (2 ', 3'-oxynaphthoylamino) -3,4-dichlorobenzene.
Example: 15.6 parts by weight of 1-amino-2-methoxybenzene-5-carboxylic acid (2 ', 5'-dichlorophenyl) amide are diazotized in the usual way. Here, the suspension of the undissolved diazonium compound is added to remove the excess mineral acid with sodium acetate and a solution of 16.6 parts by weight of 1- (2 ', 3'-OYyriaplithoylamino) -3,4- is allowed with very good stirring. dichloro1)
enzol in verclüii; i- t er <B>. </B> caustic soda. The coupling is ended by gradually heating to 40 C. The dye formed is filtered off, washed well and dried.
The product obtained in this way is a red powder that can be used in particular for coloring rubber, polyvinyl chloride or condensation products made from urea and formaldehyde or for producing paints with good oil and light resistance.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE299710X | 1950-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH299710A true CH299710A (en) | 1954-06-30 |
Family
ID=6091330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH299710D CH299710A (en) | 1950-10-20 | 1951-10-17 | Process for the preparation of a water-insoluble monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH299710A (en) |
-
1951
- 1951-10-17 CH CH299710D patent/CH299710A/en unknown
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