CH172073A - Process for the preparation of a nitroarylaminoarylamine. - Google Patents
Process for the preparation of a nitroarylaminoarylamine.Info
- Publication number
- CH172073A CH172073A CH172073DA CH172073A CH 172073 A CH172073 A CH 172073A CH 172073D A CH172073D A CH 172073DA CH 172073 A CH172073 A CH 172073A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- nitroarylaminoarylamine
- acid
- dyes
- condensation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 229960004365 benzoic acid Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- DZWVYHSGHFPXCM-UHFFFAOYSA-N 4-chloro-3-nitrobenzoic acid;sodium Chemical compound [Na].OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DZWVYHSGHFPXCM-UHFFFAOYSA-N 0.000 description 1
- DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 125000004999 nitroaryl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Nitroarylaminoarylamins. Es wurde gefunden, dass man zu wert vollen Nitrofarbstoffen gelangt, wenn man 4-Halogen-3-nitro-l-benzoesäure oder deren Ester oder Amide mit p-Aminodiphenylamin einschliesslich seinerHomologen, Substitutions- produkte und Hydrierungsprodukte konden siert.
Die Farbstoffe färben die tierische Faser in brauneu Tönen an und ergeben, soweit sie keine Sulfogrupperr enthalten, auch kräftige Färbungen auf Zelluloseestern und -äthern.
Die neuen Farbstoffe zeichnen sich in überraschender Weise vor den nach dem Verfahren des deutschen Patentes 504247 aus beispielsweise 4-Halogen-3. 5-dinitro- 1-benzoesäure erhältlichen Dinitrofarbstoffen durch bessere Lichtechtheit aus.
Die Kondensation erfolgt in Wasser oder in organischen Lösungsmitteln oder in Ge mischen beider, mit oder ohne Zusatz von säurebindenden Mitteln nach an sich bekann ten Methoden. Man kann die Herstellung der Farbstoffe auch in der Weise ausführen, dass man zum Beispiel zunächst die p-Aminodi- phenylacylverbindungen der Formel
EMI0001.0021
kondensiert und nach erfolgter Kondensation die Acylgruppe wieder abspaltet. Die Kon densation kann auch unter Druck oder in einem Stickstoffstrom erfolgen.
Gegenstand des vorliegenden Patentes ist Verfahren zur Darstellung eines Nitroaryl- aminoarylamins folgender Konstitution:
EMI0001.0025
welches dadurch gekennzeichnet ist, dass man 4-Chlor-3-rritrobetrzol-l-karbonsaures Nätrium mit 4-Aminodipherrylamin in Gegenwart eines säurebindenden Mittels kondensiert. <I>Beispiel:</I> <B>201,5</B> Gewichtsteile 4-Chlor-3-nitro-l-ben- zolkarbonsäure werden in Wasser und Soda als Natriumsalz gelöst; dazu gibt man 184 Gewichtsteile Aminodiphenylamin und einen Überschuss an Kreide.
Das Gemisch hält man dann unter Rühren bis zur Beendigung der Kondensation im Sieden. Man saugt ab, kocht den Rückstand mit verdünnter Salz säure aus und kristallisiert das- Reaktions produkt in Form des Natriumsalzes aus Wasser um. Der Farbstoff ergibt lichtechte braune Färbungen auf Acetatseide. PATENTANSPRUCH:
Verfahren zur Darstellung eines Nitro- arylaminoarylamins von folgender Konstitu tion
EMI0002.0011
dadurch gekennzeichnet, dass man 4-Chlor-3- nitrobenzol-l-karbonsaures Natrium mit 4- Aminodiphenylamin in Gegenwart eines säure bindenden Mittels kondensiert. Der Farbstoff ergibt lichtechte braune Färbungen auf
Process for the preparation of a nitroarylaminoarylamine. It has been found that valuable nitro dyes are obtained if 4-halo-3-nitro-1-benzoic acid or its esters or amides are condensed with p-aminodiphenylamine, including its homologues, substitution products and hydrogenation products.
The dyes color the animal fibers in brownish tones and, as long as they do not contain sulfo inhibitors, also produce strong colors on cellulose esters and ethers.
The new dyes are surprisingly distinguished from those of the process of German patent 504247, for example 4-halo-3. 5-dinitro-1-benzoic acid available dinitro dyes by better lightfastness.
The condensation takes place in water or in organic solvents or in mixtures of both, with or without the addition of acid-binding agents according to methods known per se. The preparation of the dyes can also be carried out in such a way that, for example, first the p-aminodiphenylacyl compounds of the formula
EMI0001.0021
condenses and after condensation the acyl group is split off again. The condensation can also take place under pressure or in a stream of nitrogen.
The present patent is a process for the preparation of a nitroaryl aminoarylamine of the following constitution:
EMI0001.0025
which is characterized in that 4-chloro-3-ritrobetrzol-1-carboxylic acid sodium is condensed with 4-aminodipherrylamine in the presence of an acid-binding agent. <I> Example: </I> <B> 201.5 </B> parts by weight of 4-chloro-3-nitro-1-benzene carboxylic acid are dissolved in water and soda as the sodium salt; 184 parts by weight of aminodiphenylamine and an excess of chalk are added to this.
The mixture is then kept at the boil with stirring until the condensation has ended. It is filtered off with suction, the residue is boiled with dilute hydrochloric acid and the reaction product is recrystallized in the form of the sodium salt from water. The dye gives light-fast brown dyeings on acetate silk. PATENT CLAIM:
Process for the preparation of a nitroarylaminoarylamine of the following constitution
EMI0002.0011
characterized in that 4-chloro-3-nitrobenzene-1-carboxylic acid sodium is condensed with 4-aminodiphenylamine in the presence of an acid-binding agent. The dye gives light-fast brown colorations
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE172073X | 1932-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH172073A true CH172073A (en) | 1934-09-30 |
Family
ID=5689835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH172073D CH172073A (en) | 1932-11-17 | 1933-11-15 | Process for the preparation of a nitroarylaminoarylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH172073A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3153667A (en) * | 1959-09-02 | 1964-10-20 | Du Pont | Process for producing diarylamino aromatic dicarboxylic acids |
-
1933
- 1933-11-15 CH CH172073D patent/CH172073A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3153667A (en) * | 1959-09-02 | 1964-10-20 | Du Pont | Process for producing diarylamino aromatic dicarboxylic acids |
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