DE504247C - Process for the preparation of water-soluble dinitroarylaminodiarylamines - Google Patents
Process for the preparation of water-soluble dinitroarylaminodiarylaminesInfo
- Publication number
- DE504247C DE504247C DEI29323D DEI0029323D DE504247C DE 504247 C DE504247 C DE 504247C DE I29323 D DEI29323 D DE I29323D DE I0029323 D DEI0029323 D DE I0029323D DE 504247 C DE504247 C DE 504247C
- Authority
- DE
- Germany
- Prior art keywords
- water
- dinitroarylaminodiarylamines
- soluble
- preparation
- brown
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C09B51/00—Nitro or nitroso dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung von wasserlöslichen Dinitroarylaminodiarylaminen Es ist gefunden worden, daß man zu wertvollen Dinitroarylaminodi:aryl:aminfarbstoffen gelangt, wenn man p-Ami:nodipheinylamin ei;nschließlich seiner Homologen und Substitttionsproduhte mit Dinitrohalogenarylen folgender Konstitution kondensiert: bedeuten soll.Process for the preparation of water-soluble dinitroarylaminodiarylamines It has been found that valuable dinitroarylaminodi: aryl: amine dyes are obtained if p-Ami: nodipheinylamine ei; including its homologues and substitution products, is condensed with dinitrohaloaryls of the following constitution: should mean.
Die Farbstoffe färben die tierische Faser in gelb- bis rotbraunen Farbtönen an und sind zum großen Teil besonders dadurch ausgezeichnet, daß sie auch echte Färbungen auf Celluloseestern und -äthern ergeben.The dyes color the animal fiber in yellow to red-brown Shades and are for the most part particularly distinguished by the fact that they also result in real colorations on cellulose esters and ethers.
Die Kondensation erfolgt in Wasser mit oder ohne Zusatz von säurebindenden Mitteln, wie Natriumacetat, Kreide usw. Beispiele. i. a78 Gewichtsteile 4-Aminodiphenylamin-4'-methyl-a-sulfosäure werden in Wasser unter Zusatz von Kreide eingerührt; dazu gibt man 371,5 Gewichtsteile und erhitzt a bis 3 Stunden auf etwa 8o bis 9o°. Das nach dem Erkalten abgesaugte Reaktionsprodukt wird in üblicher Weise in das Natronsalz übergeführt und kann aus Wasser umkriställisiert werden; es stellt ein braunes Pulver dar, welches Wolle in schön braunem Farbton anfärbt.The condensation takes place in water with or without the addition of acid-binding agents such as sodium acetate, chalk, etc. Examples. i. a78 parts by weight of 4-aminodiphenylamine-4'-methyl-a-sulfonic acid are stirred into water with the addition of chalk; 371.5 parts by weight are added and heated to about 8o to 9o ° for a to 3 hours. The reaction product sucked off after cooling is converted into the sodium salt in the usual way and can be recrystallized from water; it is a brown powder that stains wool in a beautiful brown shade.
a. In gleicher Weise wie in Beispiel i läßt man molekulare Mengen 4-Aminodiphenylamin-a-sulfosäure und 4-Chlor-3 # 5-dinitroi-benzoesäuremethylester aufeinander einwirken. Der erhaltene Farbstoff kristallisiert gleichfalls aus Wasser und zeichnet sich durch die guten Echtheiten seiner gelbbraunen Wollfärbung aus.a. Molecular quantities are allowed in the same way as in Example i 4-aminodiphenylamine-a-sulfonic acid and 4-chloro-3 # 5-dinitroi-benzoic acid methyl ester interact. The dye obtained also crystallizes from water and is characterized by the good fastness properties of its yellow-brown wool dye.
Der in analoger Weise hergestellte Farbstoff aus p-Aminodiphenylamin und 4-Chlor-3 ' 5-dinitro- i-benzoes.äure zeichnet sich besonders dadurch aus, daß er ein kräftiges Braun auf Acetylcellulose ergibt. Unter ganz ähnlichen Bedingungen gelangt man z. B. zu folgenden Farbstoffen: welche die tierische Faser in den verschiedensten Brauntönen anfärben und zum Teil auch kräftige Färbungen auf Celluloseesbern und -äthern ergeben.The dye prepared in an analogous manner from p-aminodiphenylamine and 4-chloro-3 '5-dinitro-i-benzoic acid is particularly characterized by the fact that it gives a strong brown on acetyl cellulose. Under very similar conditions you get z. B. on the following dyes: which dye the animal fibers in a wide variety of brown tones and sometimes also produce strong dyes on cellulose sebs and ethers.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI29323D DE504247C (en) | 1926-10-19 | 1926-10-19 | Process for the preparation of water-soluble dinitroarylaminodiarylamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI29323D DE504247C (en) | 1926-10-19 | 1926-10-19 | Process for the preparation of water-soluble dinitroarylaminodiarylamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE504247C true DE504247C (en) | 1930-08-13 |
Family
ID=7187283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI29323D Expired DE504247C (en) | 1926-10-19 | 1926-10-19 | Process for the preparation of water-soluble dinitroarylaminodiarylamines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE504247C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748824C (en) * | 1936-03-18 | 1945-01-18 | Process for the production of acidic wool dyes |
-
1926
- 1926-10-19 DE DEI29323D patent/DE504247C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748824C (en) * | 1936-03-18 | 1945-01-18 | Process for the production of acidic wool dyes |
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