DE221433C - - Google Patents
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- Publication number
- DE221433C DE221433C DENDAT221433D DE221433DA DE221433C DE 221433 C DE221433 C DE 221433C DE NDAT221433 D DENDAT221433 D DE NDAT221433D DE 221433D A DE221433D A DE 221433DA DE 221433 C DE221433 C DE 221433C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acid
- phenylenediamine
- aminobenzoyl
- nitrobenzoyl
- 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
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- -1 Aminophenyl Chemical group 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000003460 sulfonic acids Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- OOTIEPZZGQFJME-UHFFFAOYSA-N NN(C1=C(C=CC=C1)N)C(C1=CC=CC=C1)=O Chemical class NN(C1=C(C=CC=C1)N)C(C1=CC=CC=C1)=O OOTIEPZZGQFJME-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- VVLIWTRLJBSXLR-UHFFFAOYSA-N NC1(CC(=CC=C1)N)NC(C1=CC=CC=C1)=O Chemical compound NC1(CC(=CC=C1)N)NC(C1=CC=CC=C1)=O VVLIWTRLJBSXLR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- PFTVAIVEMNKFER-UHFFFAOYSA-N N-(3,4-dinitrophenyl)benzamide Chemical compound C1=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C1NC(=O)C1=CC=CC=C1 PFTVAIVEMNKFER-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009967 direct dyeing Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- CZUMPCZMNRCLJU-UHFFFAOYSA-N N-(2,4-diaminophenyl)benzamide Chemical compound NC1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1 CZUMPCZMNRCLJU-UHFFFAOYSA-N 0.000 description 1
- NEWHXFGKXVCSRP-UHFFFAOYSA-N N-(2,5-diaminophenyl)benzamide Chemical compound NC1=CC=C(N)C(NC(=O)C=2C=CC=CC=2)=C1 NEWHXFGKXVCSRP-UHFFFAOYSA-N 0.000 description 1
- CYYNEDNMBJDEAB-UHFFFAOYSA-N NC1(CC=C(C=C1)N)NC(C1=CC=CC=C1)=O Chemical compound NC1(CC=C(C=C1)N)NC(C1=CC=CC=C1)=O CYYNEDNMBJDEAB-UHFFFAOYSA-N 0.000 description 1
- UJGCNNDAJRLKBE-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC(=C1C)NC(C1=CC=CC=C1)=O)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1C)NC(C1=CC=CC=C1)=O)[N+](=O)[O-] UJGCNNDAJRLKBE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
-JVl 221433-KLASSE 22«. GRUPPE-JVl 221433-CLASS 22 «. GROUP
in BASEL.in Basel.
Patentiert im Deutschen Reiche vom 2. März 1909 ab. Patented in the German Empire on March 2, 1909 .
Für diese Anmeldung ist bei der Prüfung gemäß dem Unionsvertrage vomFor this registration, the examination according to the Union Treaty of
20. März 1883March 20, 1883
14. Dezember 1900 auf Grund der Anmeldung in Frankreich vom π. März 1908 anerkannt.December 14, 1900 on the basis of the registration in France from π. Recognized March 1908.
die Prioritätthe priority
Es wurde gefunden, daß man zu Farbstoffen, deren mit ß-Naphtol entwickelte Färbungen sich durch vorzügliche Waschechtheit auszeichnen, gelangt, wenn man 2 : 5 - Aminonaphtol-7-mono- bzw. -1: 7 - disulfosäure, Aminoarylacidylaminonaphtolsulfosäuren, Aminoaryl-5-oxynaphtimidazolsulfosäuren und Aminoaryl-5-oxynaphtylthiazolsulfosäuren mit Tetrazoverbindungen kuppelt, welche sich von Aminobenzoyl-m- oder p-Phenylendiamin bzw. deren Homologen ableiten. Die Darstellung dieser bisher unbekannten Verbindungen der allgemeinen FormelIt has been found that dyes whose colorations developed with β-naphtol can be obtained are characterized by excellent wash fastness, if you get 2: 5 - aminonaphtol-7-mono- or -1: 7 - disulfonic acid, aminoarylacidylaminonaphthol sulfonic acids, Aminoaryl-5-oxynaphtimidazole sulfonic acids and aminoaryl-5-oxynaphtylthiazole sulfonic acids with tetrazo compounds, which differ from aminobenzoyl-m- or p-phenylenediamine or their Derive homologues. The representation of these previously unknown connections of the general formula
,/NH-, / NH-
erfolgt zweckmäßig in der Weise, daß man entweder m- oder p-Nitranilin bzw. deren Homologen mit Nitrobenzoylchlorid kondensiert und die entstandenen Nitrobenzoylverbindungen in bekannter Weise reduziert oder aber Monoacidyl-m- oder p-Phenylendiamin bzw. deren Homologen mit Nitrobenzoylchlorid kondensiert, hierauf verseift und reduziert.expediently takes place in such a way that either m- or p-nitroaniline or their homologues condensed with nitrobenzoyl chloride and the resulting nitrobenzoyl compounds in known manner reduced or monoacidyl-m- or p-phenylenediamine or their Condensed homologues with nitrobenzoyl chloride, then saponified and reduced.
13,8 Teile m - Nitranilin werden in etwa 300 Teilen Wasser unter Zusatz von 13 Teilen Salzsäure gelöst, mit 15 Teilen kristallisiertem Natriumacetat versetzt und bei 50 ° C. ig Teile m-Nitrobenzoylchlorid zugegeben. Das Kondensationsprodukt 13.8 parts of m - nitroaniline are roughly 300 parts of water with the addition of 13 parts of hydrochloric acid dissolved, with 15 parts of crystallized Sodium acetate is added and parts of m-nitrobenzoyl chloride are added at 50.degree. The condensation product
fällt als grauer Niederschlag aus, welcher abfiltriert und in bekannter Weise, z. B. mittels Eisen und etwas Essigsäure, reduziert wird. Die so erhaltene Diamindverbindung (m-Aminobenzoyl-m-phenylendiamin) kristallisiert aus heißem Wasser in hellen Blättchen.precipitates as a gray precipitate, which is filtered off and in a known manner, for. B. by means of iron and some acetic acid, is reduced. The diamine compound thus obtained (m-aminobenzoyl-m-phenylenediamine) crystallizes from hot water in light-colored flakes.
In ähnlicher Weise verfährt man behufs Darstellung von m- oder ρ - Aminobenzoylp-phenylendiamin, o-, m- oder p-Aminobenzoylm-toluylendiamm, o- oder ρ - Aminobenzoylm-phenylendiamin. A similar procedure is used to prepare m- or ρ-aminobenzoylp-phenylenediamine, o-, m- or p-aminobenzoylm-toluenediamine, o- or ρ - aminobenzoylm-phenylenediamine.
Zur näheren Charakteristik der technisch besonders in Frage kommenden Nitrobenzoylnitroaminoverbindungen bzw. der entsprechenden Aminobenzoyldiamine diene folgende Tabelle:For more detailed characteristics of the technically particularly suitable nitrobenzoylnitroamino compounds or the corresponding aminobenzoyldiamines are used in the following table:
3030th
3535
4040
4-54-5
5050
m-Nitrobenzoyl-p-nitranilin (Schmp. 249 °) gelblich gefärbtes Pulver aus Nitro- 55m-nitrobenzoyl-p-nitroaniline (mp. 249 °) yellowish colored powder of nitro-55
benzol. m-Aminobenzoyl-p-phenylendiamin (Schmp. 150 °) .... bräunliche Nädelchen kristallisiert ausbenzene. m-aminobenzoyl-p-phenylenediamine (melting point 150 °) .... brownish needles crystallize out
Alkohol.Alcohol.
p-Nitrobenzoyl-p-nitranilin (Schmp. 266 °) blaßgelbes kristallinisches Pulver ausp-Nitrobenzoyl-p-nitroaniline (mp. 266 °) pale yellow crystalline powder from
Alkohol kristallisiert.Alcohol crystallizes.
p-Aminobenzoyl-p-phenylendiamin (Schmp. 205 °). . . . bräunliche Nadeln aus Wasser kristalli- 50p-aminobenzoyl-p-phenylenediamine (melting point 205 °). . . . brownish needles of water crystalline 50
siert.sated.
5 m-Nitrobenzoyl-m-nitranilin (Schmp. 185 °) bräunliche, feine Nädelchen aus Alkohol. 5 m-nitrobenzoyl-m-nitroaniline (melting point 185 °) brownish, fine needles made from alcohol.
m-Ammobenzoyl-m-phenylendiamin (Schmp. 130°) ... bräunliche, aus Lamellen bestehendem-Ammobenzoyl-m-phenylenediamine (melting point 130 °) ... brownish, consisting of lamellae
Kristalldrusen aus Alkohol. 55Crystal drusen made from alcohol. 55
p-Nitrobenzoyl-m-nitranilin (Schmp. 227°) gelbliche Nädelchen.p-Nitrobenzoyl-m-nitroaniline (mp. 227 °) yellowish needles.
10 p-Aminobenzoyl-m-phenylendiamin (Schmp. 1730) . . . . graues Pulver.10 p-aminobenzoyl-m-phenylenediamine (m.p. 173 0 ). . . . gray powder.
m-Nitrobenzoyl-p-nitro-o-toluidin (Schmp. 193°). glänzende, nahezu weiße Blättchen ausm-nitrobenzoyl-p-nitro-o-toluidine (mp. 193 °). shiny, almost white leaves
Alkohol.Alcohol.
m-Aminobenzoyl-m-toluylendiamin (Schmp. 17J°) .... bräunliches kristallinisches Pulver aus 60m-aminobenzoyl-m-toluylenediamine (melting point 17J °) .... brownish crystalline powder from 60
Methylalkohol. 15 p-Nitrobenzoyl-p-nitro-o-toluidin (Schmp. 2140) bräunlich gelbe Nadeln aus Alkohol.Methyl alcohol. 15 p-Nitrobenzoyl-p-nitro-o-toluidine (mp. 214 0 ) brownish yellow needles from alcohol.
11,4 Teile m-Aminobenzoyl-m-phenylendiamin werden in 200 bis 300 Teilen Wasser unter Zusatz von 30 Teilen Salzsäure heiß gelöst, nach Erkalten der Lösung mit 7,2 Teilen Natriumnitrit tetrazotiert und die Tetrazolösung mit einer sodaalkalischen Lösung von 32 Teilen 2 : 5-Aminonaphtol-i: 7 - disulfosäure vereinigt. Nach erfolgter Kombination wird aufgekocht, ausgesalzen und filtriert. Der Farbstoff bildet ein in Wasser mit orangegelber Farbe lösliches, braunrotes Pulver. In konzentrierter Schwefelsäure löst er sich mit gelbroter Farbe. Die direkte Baumwollfärbung besitzt eine orangefarbige Nuance und geht beim Diazotieren und Entwickeln mit ,8-Naphtal in ein klares Blaurot über.11.4 parts of m-aminobenzoyl-m-phenylenediamine are dissolved hot in 200 to 300 parts of water with the addition of 30 parts of hydrochloric acid, after cooling the solution tetrazotized with 7.2 parts of sodium nitrite and the tetrazole solution combined with a soda-alkaline solution of 32 parts of 2: 5-aminonaphthol-i: 7 - disulfonic acid. After the combination has been made, it is boiled, salted out and filtered. The dye forms a brown-red powder soluble in water with an orange-yellow color. In concentrated Sulfuric acid dissolves with a yellow-red color. The direct cotton dye has a Orange shade and goes into 8-naphthalene when diazotized and developed clear blue red over.
Die nach Beispiel 2 erhaltene Tetrazolösung läßt man in eine alkalische Lösung von 36 Teilen m-Aminobenzoyl-2:5-aminonaphtol-7-sulfosäure einlaufen. Der Farbstoff liefert auf Baumwolle in direkter Färbung rote Nuancen, die beim Entwickeln mit ß-Naphtol in Rotorange übergehen.The tetrazo solution obtained according to Example 2 is left in an alkaline solution of 36 parts of m-aminobenzoyl-2: 5-aminonaphthol-7-sulfonic acid come in. The dye provides red nuances in direct dyeing on cotton, which when developed with ß-naphtol change to red-orange.
Die aus 11,4 Teilen m-Aminobenzoyl-m-phenylendiamm dargestellte Tetrazolösung wirdThe 11.4 parts of m-aminobenzoyl-m-phenylenediamine shown tetrazo solution is
mit Soda neutralisiert, hierauf eine Lösung von 12 Teilen 2: 5-Aminonaphtol-7-sulfosäure und 20 Teilen Soda in 200 Teilen Wasser zugefügt. Nachdem die Bildung des Zwischenproduktes beendet ist, läßt man eine Lösung von 18Teilenm- oder p-Aminobenzoyl-2: 5-naphtol-7-sulfosäure zufließen, kocht nach einiger Zeit auf und salzt den Farbstoff aus. Er färbt Baumwolle in direkter Färbung rot an. Die mit ß-Naphtol entwickelten Färbungen besitzen eine bräunlich-bordeauxrote Nuance.neutralized with soda, then a solution of 12 parts of 2: 5-aminonaphthol-7-sulfonic acid and 20 parts of soda in 200 parts of water were added. After the formation of the intermediate is complete, a solution of 18 parts of m- or p-aminobenzoyl-2: 5-naphthol-7-sulfonic acid is left flow in, boils up after a while and salt out the dye. It stains cotton red in direct dyeing. The colorations developed with ß-naphtol have a brownish-burgundy shade.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE221433C true DE221433C (en) |
Family
ID=482406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT221433D Active DE221433C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE221433C (en) |
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