CH145831A - 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
- CH145831A CH145831A CH145831DA CH145831A CH 145831 A CH145831 A CH 145831A CH 145831D A CH145831D A CH 145831DA CH 145831 A CH145831 A CH 145831A
- Authority
- CH
- Switzerland
- Prior art keywords
- cotton
- fiber
- pulls
- compound
- diazotized
- Prior art date
Links
- 229920000742 Cotton Polymers 0.000 title claims description 5
- 239000000835 fiber Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000006722 reduction reaction Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- XIBQBHVJHOIQIH-UHFFFAOYSA-N 5-nitro-2-[(4-nitrobenzoyl)amino]benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 XIBQBHVJHOIQIH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 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
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PHYYRWFTRXRAQA-UHFFFAOYSA-N 2-[(4-nitrobenzoyl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 PHYYRWFTRXRAQA-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 description 1
- 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent 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
- 239000008103 glucose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229940073020 nitrol Drugs 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer auf die Baumwolle ziehenden und auf der Faser diazotierbaren Verbindung. Das den Gegenstand vorliegender Erfin dung bildende Verfahren ist dadurch ge kennzeichnet, dass man aus 2 Molekülen 1-(4'- Nitrobenzoylamino) -4-nitrol)e nzol- 2- carbon- säure
EMI0001.0009
erhältlich durch Kondensation von 4-Nitro- 1-aminobenzol-2-carbonsäure mit 4-Nitroben- zoylchlorid oder durch Nitrieren von 1-(4 Nitrobenzoylamino)
- Benzol - 2 - carbonsäure, durch vorsichtige Reduktion je einer Nitro gruppe, wobei Bindung zwischen den Stick stoffatomen stattfindet, und eine sich an schliessende Reduktion der beiden übrigblei- betiden Nitrogruppen zu Aminogruppen eine schwach gelb gefärbte Verbindung herstellt, die als Natriumsalz in Wasser leicht löslich ist, und aus der wässerigen Lösung mit blass- gelber Farbe auf Baumwolle zieht.
Durch Diazotieren auf der Faser und Kuppeln mit 1-Phenyl-3-methyl-5-pyrazolon erhält man ein kräftiges lebhaftes grünstichiges Gelb von sehr guter Wasch- und Lichtechtheit. Die beiden Reduktionsreaktionen kann man in einem Arbeitsgange ausführen.
<I>Beispiel:</I> 33,3 Teile 1-(4'-Nitrobenzoylamino)-4- nitrobenzol-2-carbonsäure werden unter Rüh ren in eine kochende Mischung von 500 Tei len Wasser, 33 Teilen Zinkstaub und 10 Tei len Essigsäure<B>98%</B> rasch eingetragen, wor auf noch 5-10 Minuten die Masse im Sie- den gehalten wird. Man verdünnt mit 700 Teilen Wasser, macht mit 12 Teilen Nat.rium- carbonat schwach alkalisch und trennt die Flüssigkeit vom Zinkoxydschlamm. Das beim Abkühlen sich ausscheidende Reaktionspro dukt filtriert man ab und trocknet es.
Als Reduktionsmittel kann man u. a. auch Natriumsulfid, Glucose oder arsenige Säure verwenden.
Process for the preparation of a compound which pulls on the cotton and can be diazotized on the fiber. The method forming the subject of the present invention is characterized in that 1- (4'-nitrobenzoylamino) -4-nitrol) e nzene-2-carboxylic acid is obtained from 2 molecules
EMI0001.0009
obtainable by condensation of 4-nitro-1-aminobenzene-2-carboxylic acid with 4-nitrobenzoyl chloride or by nitrating 1- (4 nitrobenzoylamino)
- Benzene - 2 - carboxylic acid, by careful reduction of one nitro group each, whereby binding takes place between the nitrogen atoms, and a subsequent reduction of the two remaining nitro groups to amino groups produces a pale yellow colored compound, which as the sodium salt in water easily is soluble, and pulls from the aqueous solution with pale yellow color on cotton.
Diazotization on the fiber and coupling with 1-phenyl-3-methyl-5-pyrazolone gives a strong, vivid greenish yellow of very good wash and lightfastness. The two reduction reactions can be carried out in one operation.
<I> Example: </I> 33.3 parts of 1- (4'-nitrobenzoylamino) -4-nitrobenzene-2-carboxylic acid are stirred into a boiling mixture of 500 parts of water, 33 parts of zinc dust and 10 parts Acetic acid <B> 98% </B> is quickly added, whereupon the mixture is kept in the boil for another 5-10 minutes. It is diluted with 700 parts of water, made weakly alkaline with 12 parts of sodium carbonate and the liquid is separated from the zinc oxide sludge. The reaction product which separates out on cooling is filtered off and dried.
As a reducing agent you can u. a. also use sodium sulfide, glucose or arsenic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH140099T | 1929-01-14 | ||
| DE145831X | 1929-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH145831A true CH145831A (en) | 1931-03-15 |
Family
ID=25713470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH145831D CH145831A (en) | 1929-01-14 | 1929-09-13 | Process for the preparation of a compound which pulls on the cotton and can be diazotized on the fiber. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH145831A (en) |
-
1929
- 1929-09-13 CH CH145831D patent/CH145831A/en unknown
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