DE188819C - - Google Patents
Info
- Publication number
- DE188819C DE188819C DENDAT188819D DE188819DA DE188819C DE 188819 C DE188819 C DE 188819C DE NDAT188819 D DENDAT188819 D DE NDAT188819D DE 188819D A DE188819D A DE 188819DA DE 188819 C DE188819 C DE 188819C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- solution
- added
- dye
- oxide hydrate
- 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 8
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000920 calcium hydroxide Substances 0.000 claims description 4
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- ZKGFCAMLARKROZ-UHFFFAOYSA-N oxozinc;hydrate Chemical compound O.[Zn]=O ZKGFCAMLARKROZ-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 7
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YYSVBOXCBRNESR-UHFFFAOYSA-N 2-(chloroamino)-3-nitrophenol Chemical compound [N+](=O)([O-])C=1C(=C(C=CC=1)O)NCl YYSVBOXCBRNESR-UHFFFAOYSA-N 0.000 description 2
- NCBBZXRTYWOPLK-UHFFFAOYSA-N 2-nitramidooxybenzoic acid Chemical compound [N+](=O)([O-])NOC=1C(C(=O)O)=CC=CC=1 NCBBZXRTYWOPLK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- DZQXQAXLDXJEAG-UHFFFAOYSA-N n-(2-hydroxyphenyl)nitramide Chemical compound OC1=CC=CC=C1N[N+]([O-])=O DZQXQAXLDXJEAG-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical class NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 1
- WZSBYBXNPKFJTA-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrophenol Chemical compound CC1=CC(N)=C(O)C=C1[N+]([O-])=O WZSBYBXNPKFJTA-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- OUHREBGMGVQVQJ-UHFFFAOYSA-N 5-diazo-6-nitrocyclohexa-1,3-dien-1-ol Chemical class OC1=CC=CC(=[N+]=[N-])C1[N+]([O-])=O OUHREBGMGVQVQJ-UHFFFAOYSA-N 0.000 description 1
- KDEURZJJYFEAKC-UHFFFAOYSA-N N-(3-hydroxy-2-methylphenyl)nitramide Chemical compound [N+](=O)([O-])NC1=C(C(=CC=C1)O)C KDEURZJJYFEAKC-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- FKLRBKPRLBWRKK-UHFFFAOYSA-N magnesium;oxygen(2-);hydrate Chemical compound O.[O-2].[Mg+2] FKLRBKPRLBWRKK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift 184689 wurde einIn the patent 184689 a
Verfahren zur Darstellung von Azofarbstoffen, die sich von der Chromotropsäure ableiten, beschrieben, das darin besteht, daß man diejenigen diazotierten Nitro-o-aminophenole in Gegenwart von Kalkhydrat mit Chromotropsäure kombiniert, welche zugleich p-Nitranilinderivate sind, z. B. Nitroaminophenol Process for the preparation of azo dyes, which are derived from the chromotropic acid, described, which consists in the fact that those diazotized nitro-o-aminophenols combined in the presence of hydrated lime with chromotropic acid, which are also p-nitroaniline derivatives, e.g. B. nitroaminophenol
NH2- OH-NO2 = 1 -.2: 4,NH 2 - OH-NO 2 = 1-2: 4,
NitroaminokresolNitroaminocresol
CHB = 1:2:4:5,
ig Nitrochloraminophenol CH B = 1: 2: 4: 5,
ig nitrochloraminophenol
NH2- OH. N0.2- Cl = ι : 2 : 4 : 5,
Nitroaminooxybenzoesäure NH 2 - OH. N0. 2 - Cl = ι: 2: 4: 5,
Nitroaminooxybenzoic acid
NH2. O H'. NO2- C O O H = 1:2:4:5. 20 NH 2 . O H '. NO 2 - COOH = 1: 2: 4: 5. 20th
Die auffallende Wirkungsweise des Kalkhydrats, nämlich der glatte Reaktionsverlauf in dessen Gegenwart im Gegensatz zu üblichen Azokombinationsbedingungen, bleibt zunächst unerklärt. Es wurde bei weiterer Untersuchung gefunden, daß auch andere Erdalkalioxydhydrate, sowie Magnesium- und Zinkoxydhydrat die Umsetzung der in Rede stehenden Diazonitrophenole mit Chromotropsäure zum Monoazofarbstoffe wie Kalkhydrat gleich günstig beeinflussen. Verwendet man Magnesium- oder Zinkoxydhydrat in solchem Verfahren, so ist es angezeigt, die Temperatur bei etwa 30 bis 40° zu halten, um,die sonst langsam erfolgende Umsetzung zu beschleunigen. The striking mode of action of hydrated lime, namely the smooth course of the reaction in its presence, in contrast to the usual azo combination conditions, remains initially unexplained. Upon further investigation it was found that others Alkaline earth oxide hydrates, as well as magnesium and zinc oxide hydrate, the implementation of the talk standing diazonitrophenols with chromotropic acid to monoazo dyes such as hydrated lime affect equally favorably. If one uses magnesium or zinc oxide hydrate in such Procedure, it is indicated to keep the temperature at around 30 to 40 ° in order to achieve that otherwise slow implementation to accelerate.
Zu der Lösung von 38 kg des Dinatriumsalzes der Chromotropsäure gibt man 25 kg Zinkoxydhydrat und die aus 15,4kg Nitroaminophenol 25 kg are added to the solution of 38 kg of the disodium salt of chromotropic acid Zinc oxide hydrate and that from 15.4kg nitroaminophenol
NH2. O H. NO2 = I :2: 4 NH 2 . O H. NO 2 = I : 2: 4
mit 25 kg Salzsäure (20 ° Be) und 6,9 kg Nitrit dargestellte Diazoverbindung. Man erwärmt unter Umrühren auf 30 bis 35 °. Im Verlauf einiger Stunden ist dann die Farbstoffbildung beendet. Durch Ansäuern mit Salzsäure und Zugabe von Kochsalz scheidet man den Farbstoff ab, dessen Eigenschaften schon in der Patentschrift 184689 beschrieben sind.diazo compound prepared with 25 kg of hydrochloric acid (20 ° Be) and 6.9 kg of nitrite. One warms up with stirring to 30 to 35 °. In the course of a few hours, the dye is then formed completed. Acidification with hydrochloric acid and addition of common salt separates the dye and its properties are already described in patent 184689.
5555
Beispiel II.
18,6 kg Nitrochloraminophenol
NH2.0H-NO2-Cl= I : 2 : 4 : 5Example II.
18.6 kg of nitrochloraminophenol
NH 2 .0H-NO 2 -Cl = I: 2: 4: 5
werden wie üblich in die Diazoverbindung übergeführt und diese in die Lösung von 38 kg des. Dinatriumsalzes der Chromotropsäure eingetragen, zu welcher Magnesiumoxydhydrat hinzugegeben ist, frisch hergestellt durch Fällen von 40 kg Bittersalz mit äquivalenter Menge Natronlauge. Man erwärmt allmählich auf 300. Die Farbstoffbildung vollzieht sich im Laufe mehrerer Stunden; dann wird filtriert, angesäuert undare converted into the diazo compound as usual and this is added to the solution of 38 kg of the disodium salt of chromotropic acid, to which magnesium oxide hydrate has been added, freshly prepared by precipitating 40 kg of Epsom salt with an equivalent amount of sodium hydroxide solution. The mixture is gradually warmed to 30 ° . The dye formation takes place in the course of several hours; then it is filtered, acidified and
Kochsalz zugegeben, um den schon beschriebenen Farbstoff abzuscheiden.Table salt added to deposit the dye already described.
Beispiel III.Example III.
Die aus 16,8' kg 5-Nitro-2-amino-p-kresol wie üblich erhaltene Diazoverbindung wird in die mit 50 kg Barythydrat versetzte' Lösung von 38 kg des Dinatriumsalzes der Chromotropsäure eingetragen. Nach mehrstündigem Rühren filtriert man und scheidet den bekannten Farbstoff aus der Lösung durch Ansäuern mit Salzsäure und Zugabe von Kochsalz ab.The diazo compound obtained as usual from 16.8 kg of 5-nitro-2-amino-p-cresol is in the 'solution of 38 kg of the disodium salt added with 50 kg of baryta hydrate Chromotropic acid entered. After several hours of stirring, the mixture is filtered and separated the known dye from the solution by acidification with hydrochloric acid and addition of common salt.
kg Nitroaminooxybenzoesäure
-OH-NO9 'COOH= ι : ;kg nitroaminooxybenzoic acid
-OH-NO 9 'COOH = ι:;
19,!
NH2 19 ,!
NH 2
■4: 5 werden nach üblicher Methode in die Diazoverbindung übergeführt und diese in eine mit 50 kg Barythydrat versehene Lösung von 38 kg des Dinatriumsalzes der Chromotropsäure eingetragen. , Nach" mehrstündigem Rühren filtriert man und scheidet den schon bekannten Farbstoff aus der Lösung durch Salzsäure und Kochsalz ab. ■ 4: 5 are converted into the diazo compound by the usual method and this is added to a solution of 38 kg of the disodium salt of chromotropic acid provided with 50 kg of barythydrate. After several hours of stirring, the mixture is filtered and the known dye is separated from the solution by means of hydrochloric acid and common salt.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE188819C true DE188819C (en) |
Family
ID=452413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT188819D Active DE188819C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE188819C (en) |
-
0
- DE DENDAT188819D patent/DE188819C/de active Active
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