DE147530C - - Google Patents
Info
- Publication number
- DE147530C DE147530C DENDAT147530D DE147530DA DE147530C DE 147530 C DE147530 C DE 147530C DE NDAT147530 D DENDAT147530 D DE NDAT147530D DE 147530D A DE147530D A DE 147530DA DE 147530 C DE147530 C DE 147530C
- Authority
- DE
- Germany
- Prior art keywords
- acetyl
- amido
- acid
- amidophenol
- acidyl
- 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.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 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 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 240000002799 Prunus avium Species 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Wie weitere Versuche ergeben haben, erstreckt sich die Eigenschaft, sich mit Diazoverbindungen kombinieren zu lassen, nicht auf das Acidyl-p-amidophenol allein; auch Derivate dieses Körpers, bei welchen noch eine Orthostelle zur Hydroxylgruppe frei ist, reagieren in gleicher Weise und ergeben Farbstoffe, welche ganz ähnliche Eigenschaften zeigen, wie diejenigen aus Acidylamidophenol.As further experiments have shown, the property extends with diazo compounds not to combine the acidyl-p-amidophenol alone; even Derivatives of this body in which one ortho position to the hydroxyl group is still free, react in the same way and give dyes which have very similar properties show how those from acidylamidophenol.
Wie das p-Amidophenol selbst, so sind auch die hier in Betracht kommenden Derivate desselben nicht imstande, sich mit Diazoverbindungen zu kombinieren; erst nach Besetzung der Amidogruppe durch einen Säurerest erhalten sie diese Eigenschaft.Like the p-amidophenol itself, so are the derivatives that come into consideration here unable to combine with diazo compounds; only after occupation the amido group by means of an acid residue gives them this property.
Als solche substituierte Acidylamidophenole, welche bis jetzt nicht beschrieben zu sein scheinen, kommen in Betracht:As such, substituted acidylamidophenols, which have not yet been described seem to come into consideration:
i. Die Acetylamidophenolsulfosäure, dargestellt durch Einwirkung von Essigsäureanhydrid auf eine wässerige Suspension von Amidophenolsulf osäurei. The acetylamidophenol sulfonic acid, shown by the action of acetic anhydride on an aqueous suspension of amidophenolsulfonic acid
(OH: NH2 (OH: NH 2
SO3HSO 3 H
1:4:2)1: 4: 2)
in Gegenwart von Natriumacetat. Die Acetylverbindung bildet weiße Nadeln, die in Wasser leicht löslich sind; dieselben schmelzen bei hoher Temperatur unter Zersetzung.in the presence of sodium acetate. The acetyl compound forms white needles that appear in water are easily soluble; they melt at high temperature with decomposition.
2. Acetylamido-o-chlorphenol, welches erhalten wird durch Kochen von 4-Amido-2-chlorphenol mit Eisessig. Es ist in kaltem Wasser, schwer, in heißem leicht löslich und kristallisiert daraus in weißen Nadeln vom F. P. 144°.2. Acetylamido-o-chlorophenol, which is obtained is made by boiling 4-amido-2-chlorophenol with glacial acetic acid. It's in cold Water, difficult, easily soluble in hot and crystallizes from it in white needles from the F. P. 144 °.
3. Acetylamido-o-kresol. Das durch die Einwirkung von Essigsäureanhydrid auf 5-Amido-2-kresol erhaltene Produkt ist in heißem Wasser ziemlich leicht löslich und kristallisiert daraus in weißen Nadeln vom F. P. 1790.3. Acetylamido-o-cresol. The product obtained by the action of acetic anhydride on 5-amido-2-cresol is quite easily soluble in hot water and crystallizes from it in white needles of FP 179 0 .
Beispiel zur Darstellung der Farbstoffe.Example for the representation of the dyes.
I. 24,6 kg Naphthionat werden in üblicher Weise diazotiert und in eine auf io° abgekühlte Lösung von 23 kg Acetylamidophenolsulfosäure und 22 kg Soda in 5001 Wasser einfließen gelassen. Nach zwölfstündigem Rühren ist die Farbstoffbildung vollendet und der Ansatz kann ausgesalzen werden.I. 24.6 kg of naphthionate are diazotized in the usual way and cooled to 10 ° in a Solution of 23 kg of acetylamidophenol sulfonic acid and 22 kg of soda in 500 l of water let in. After stirring for twelve hours, the dye formation is complete and the approach can be salted out.
II. Man läßt die aus 24,6 kg Naphthionat hergestellte Diazoverbindung in eine auf 8° abgekühlte und durch Zusatz von 15 kg Soda alkalisch gehaltene Lösung von 16,5 kg Acetylamido-o-kresol in 11 kg Natronlauge von 30 Prozent und 500 1 Wasser unter gutem Umrühren einfließen. Die Kombination geht rasch vor sich. Nach 24 Stunden wird der Farbstoff mit Salz abgeschieden, gepreßt und getrocknet.II. The diazo compound prepared from 24.6 kg of naphthionate is left in an at 8 ° cooled solution of 16.5 kg acetylamido-o-cresol kept alkaline by adding 15 kg of soda in 11 kg sodium hydroxide solution of 30 percent and 500 liters of water under good Pour in stirring. The combination goes on quickly. After 24 hours the Dye deposited with salt, pressed and dried.
Aus nachstehender Tabelle sind die Eigenschaften der Farbstoffe ersichtlich.The properties of the dyes can be seen in the table below.
in
Wassersolution
in
water
von
Natronlaugeadditive
from
Caustic soda
von
Salzsäureadditive
from
hydrochloric acid
in konz.
H2SO1 solution
in conc.
H 2 SO 1
in saurem
BadeDyes wool
in sour
Bath
färbung,
nach-
■ chromiertacid
coloring,
after-
■ chrome-plated
Naphthionsäure-azo-
acetylamidophenol-
sulfosäure5
Naphthionic acid azo
acetylamidophenol
sulfonic acid
■ gelbdirty-
■ yellow
lo acetylamidochlorphenolNaphthionic acid azo
lo acetylamidochlorophenol
blaurotdirty
blue red
gelber
Niederschlagbrownish
yellower
Precipitation
violettrotdirty-
purple red
acetylamidokresolNaphthionic acid azo
acetylamidocresol
Niederschlagdark yellow
Precipitation
Claims (1)
Neuerung in dem durch Patent 146265 geschützten Verfahren zur Darstellung nachchromierbarer Monoazofarbstoffe, darin bestehend, daß man das im Haupt-Patent angeführte Acidyl-p-amidophenol ersetztPatent claim:
Innovation in the process for the preparation of post-chromable monoazo dyes, which is protected by patent 146265, consists in replacing the acidyl-p-amidophenol mentioned in the main patent
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE147530C true DE147530C (en) |
Family
ID=414699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT147530D Active DE147530C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE147530C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5258598A (en) * | 1990-06-15 | 1993-11-02 | Comau S.P.A. | Station for assembling pressed sheet-metal structures with welding robots also usable periodically for checking the fixtures used in the station |
-
0
- DE DENDAT147530D patent/DE147530C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5258598A (en) * | 1990-06-15 | 1993-11-02 | Comau S.P.A. | Station for assembling pressed sheet-metal structures with welding robots also usable periodically for checking the fixtures used in the station |
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