CH140099A - Process for the preparation of a compound which pulls on the cotton and can be diazotized on the fiber. - Google Patents
Process for the preparation of a compound which pulls on the cotton and can be diazotized on the fiber.Info
- Publication number
- CH140099A CH140099A CH140099DA CH140099A CH 140099 A CH140099 A CH 140099A CH 140099D A CH140099D A CH 140099DA CH 140099 A CH140099 A CH 140099A
- Authority
- CH
- Switzerland
- Prior art keywords
- fiber
- pulls
- cotton
- compound
- diazotized
- Prior art date
Links
- 229920000742 Cotton Polymers 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 title claims description 6
- 239000000835 fiber Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 Nitrobenzoyl amino Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 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
- C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer auf die Baumwolle ziehenden und auf der Faser diazotierbaren Verbindung. Nitrobenzoylarninoärylsulfosäuren und Di- (nitrobenzoylamino)-arylsulfosäuren hat man durch Reduktion in die entsprechenden Amino- verbindungen übergeführt.
Wie gefunden wurde, gelingt es, durch vorsichtige Reduktion von Sulfosäuren nitro- benzoylierteraromatischer Aminoverbindungen mehrere Moleküle miteinander durch Über gang je zweier Nitrogruppen in die Azo- oder Azoxygruppe zu verknüpfen. Die freie Amino- gruppen enthaltenden Verbindungen dieser Art ziehen aus der wässerigen Lösung ihrer Salze auf Baumwolle auf und lassen sich auf der Faser diazotieren und zu Farbstoffen kuppeln.
Das den Gegenstand vorliegender Erfin dung bildende Verfahren ist dadurch gekenn zeichnet, dass man aus zwei Molekülen 1-Amino -4 - (4'- nitrobenzoylamino) - benzol-2- sulfosKure
EMI0001.0021
durch vorsichtige Reduktion der beiden Nitro- gruppen, wobei Bindung zwischen den Stick stoffatomen stattfindet, eine schwach gelb gefärbte Verbindung herstellt, die als Natrium salz in Wasser leicht löslich ist und aus der wässerigen Lösung mit blassgelber Farbe auf Baumwolle zieht.
Durch Diazotieren auf der Faser und Kuppeln mit 1-Phenyl-3-methyl- 5-pyrazolon erhält man ein kräftiges grün- stichiges Gelb.
Beispiel <I>1:</I> 36,7 Teile 1-amino-4-(4'-nitrobenzoylamino)- benzol-2-sulfosaures Natrium werden in 1000 Teilen Wasser gelöst. Bei 20 setzt man eine Lösung von 4 Teilen Natriumhydroxyd und 7,8 Teilen wasserfreiem Natriumsulfid zu und lässt bis zum Verschwinden des Sul fids rühren. Die abgeschiedene gelbe Ver- Bindung trennt man durch Filtrieren von der Lauge und löst sie aus Wasser um.
<I>Beispiel 2:</I> In eine Lösung von 33,7 Teilen 1-Amino- 4-(4'-nitrobenzoylainino)-benzol-2-sulfosäure in 600 Teilen Wasser und 30 Teilen Natron lauge (40 B6) lässt man bei 50 eine Lösung von 16 Teilen Glukose in 100 Teilen Wasser einlaufen und steigert dann die Temperatur auf 60-70 . Nach einiger Zeit scheidet sich schon in der Hitze ein hellgelber, kristalli nischer Niederschlag ab, der abfiltriert, mit Salzwasser neutral gewaschen und getrocknet wird.
Als Reduktionsmittel kann man unter andern auch arsenige Säure oder Zinkstaub verwenden.
Process for the preparation of a compound which pulls on the cotton and can be diazotized on the fiber. Nitrobenzoyl amino aryl sulfonic acids and di- (nitrobenzoylamino) aryl sulfonic acids have been converted into the corresponding amino compounds by reduction.
As has been found, it is possible to link several molecules with one another by carefully reducing sulfonic acids of nitrobenzoylated aromatic amino compounds by converting two nitro groups into the azo or azoxy group. The compounds of this type containing free amino groups are absorbed from the aqueous solution of their salts on cotton and can be diazotized on the fiber and coupled to form dyes.
The method forming the subject of the present invention is characterized in that 1-amino-4 - (4'-nitrobenzoylamino) - benzene-2-sulfosulfurized from two molecules
EMI0001.0021
through careful reduction of the two nitro groups, whereby bonding takes place between the nitrogen atoms, creates a pale yellow-colored compound which, as sodium salt, is easily soluble in water and pulls from the aqueous solution with a pale yellow color onto cotton.
Diazotization on the fiber and coupling with 1-phenyl-3-methyl-5-pyrazolone gives a strong greenish yellow.
Example <I> 1 </I> 36.7 parts of 1-amino-4- (4'-nitrobenzoylamino) -benzen-2-sulphonic acid sodium are dissolved in 1000 parts of water. At 20, a solution of 4 parts of sodium hydroxide and 7.8 parts of anhydrous sodium sulfide is added and the mixture is stirred until the sulphide has disappeared. The deposited yellow compound is separated from the alkaline solution by filtration and dissolved in water.
Example 2: In a solution of 33.7 parts of 1-amino-4- (4'-nitrobenzoylainino) -benzene-2-sulfonic acid in 600 parts of water and 30 parts of sodium hydroxide solution (40 B6) a solution of 16 parts of glucose in 100 parts of water is run in at 50 and the temperature is then increased to 60-70. After a while, a pale yellow crystalline precipitate separates out in the heat, which is filtered off, washed neutral with salt water and dried.
Arsenic acid or zinc dust can also be used as reducing agent.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI0033237 | 1928-01-18 | ||
| CH140099T | 1929-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH140099A true CH140099A (en) | 1930-03-31 |
Family
ID=88513724
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH144480D CH144480A (en) | 1928-01-18 | 1929-01-14 | Process for the preparation of a compound which pulls on the cotton and can be diazotized on the fiber. |
| CH140099D CH140099A (en) | 1928-01-18 | 1929-01-14 | Process for the preparation of a compound which pulls on the cotton and can be diazotized on the fiber. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH144480D CH144480A (en) | 1928-01-18 | 1929-01-14 | Process for the preparation of a compound which pulls on the cotton and can be diazotized on the fiber. |
Country Status (3)
| Country | Link |
|---|---|
| CH (2) | CH144480A (en) |
| DE (1) | DE565478C (en) |
| FR (1) | FR667108A (en) |
-
1928
- 1928-01-19 DE DEI33237A patent/DE565478C/en not_active Expired
-
1929
- 1929-01-09 FR FR667108D patent/FR667108A/en not_active Expired
- 1929-01-14 CH CH144480D patent/CH144480A/en unknown
- 1929-01-14 CH CH140099D patent/CH140099A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR667108A (en) | 1929-10-12 |
| CH144480A (en) | 1930-12-31 |
| DE565478C (en) | 1932-12-01 |
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