DE116351C - - Google Patents
Info
- Publication number
- DE116351C DE116351C DENDAT116351D DE116351DA DE116351C DE 116351 C DE116351 C DE 116351C DE NDAT116351 D DENDAT116351 D DE NDAT116351D DE 116351D A DE116351D A DE 116351DA DE 116351 C DE116351 C DE 116351C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- naphthylamine
- naphtol
- water
- black
- 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
- 239000002253 acid Substances 0.000 claims description 9
- 239000000975 dye Substances 0.000 claims description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 claims 1
- LZYDMBZSLOSYOZ-UHFFFAOYSA-N 4-chloro-2-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1[N+]([O-])=O LZYDMBZSLOSYOZ-UHFFFAOYSA-N 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- GWZDSIJCTLAIAT-UHFFFAOYSA-N [N+](=[N-])(S(=O)(=O)O)S(=O)(=O)O Chemical compound [N+](=[N-])(S(=O)(=O)O)S(=O)(=O)O GWZDSIJCTLAIAT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HMLCSHKCTWSSDQ-UHFFFAOYSA-M sodium;2-chloro-4-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C(Cl)=C1 HMLCSHKCTWSSDQ-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
Vi: 116351 KLASSE 22 a. Vi: 116351 CLASS 22 a.
o-m^disulfosäure.o-m ^ disulfonic acid.
Patentirt im Deutschen Reiche vom 23. März 1900 ab.Patented in the German Empire on March 23, 1900.
Wenn man p-phenylendiaminsulfosaures und p-nitrochlorbenzolsulfosaures Natron in Lösung zusammen erhitzt, so bildet sich quantitativ die p-Nitro-p'-amidodiphenylamin-o-m'-disulfosäure nach der GleichungIf you p-phenylenediaminesulfosaures and sodium p-nitrochlorobenzenesulfonate in solution When heated together, the p-nitro-p'-amidodiphenylamine-o-m'-disulfonic acid is quantitatively formed according to the equation
SO,NaSO, well
NH,NH,
NH,NH,
N ΆN Ά
,SOvNa, SOvNa
NH \Λ/ NH \ Λ /
NO,NO,
+ NaCl.+ NaCl.
Dieselbe wird durch salpetrige Säure in eine Diazoverbindung übergeführt, die sich mit Aminen und Phenolen combiniren läfst.It is converted into a diazo compound by nitrous acid, which is mixed with Amines and phenols can be combined.
Als besonders werthvoll haben sich einige aus jener Diazodisulfosäure abgeleiteten Farbstoffe der Naphtolschwarz- und Naphtylaminschwarzgruppe erwiesen. Dieselben zeichnen sich von den bekannten Repräsentanten jener Farbklasse, insbesondere auch von den betreffenden Producten der französischen Patentschrift 249661 durch ihre Farbstärke, Walkechtheit, Egalisirangsfähigkeit und Decaturechtheit aus. ■ Sie lassen sich ferner mit Chrombeizen fixiren.Some dyes derived from that diazodisulfonic acid have proven to be particularly valuable the naphtol black and naphtylamine black groups. They stand out from the well-known representatives of that Color class, in particular also from the relevant products of the French patent specification 249661 due to their color strength, millfastness, leveling ability and decatility the end. ■ They can also be fixed with chrome stains.
38,9 kg Nitroamidodiphenylamindisulfosäure werden in Wasser gelöst und mit Hülfe von 6,9 kg Nitrit und 30 kg Salzsäure diazotirt. Die Diazoverbindung, die sich nach kurzer Zeit als Gallerte abscheidet, wird in die wässerige Lösung von 14,3 kg a-Naphtylamin und 11 kg Salzsäure eingetragen. Man stumpft die freie Mineralsäure dann nach und nach mit Acetat ab. Nach ca. 12 Stunden ist die Amidoazodisulfosäure in Form eines dunkelvioletten Niederschlages abgeschieden. Dieser wird abfiltrirt und in Wasser unter Zugabe der erforderlichen Menge Natronlauge gelöst. Zur Lösung fügt man bei einer Temperatur von ca. 50C. 7 kg Nitrit und 30 kg Salzsäure hinzu und läfst einige Stunden stehen. Die gebildete Diazoazodisulfosäure ist mit blauer Farbe in Wasser löslich. Trägt man sie in die mit Soda alkalisch gehaltene Lösung von 22,4 kg ßj-ßg-Naphtolsulfosäure ein, so scheidet sich der gebildete secundäre Disazofarbstoff in Form eines krystallinischen Niederschlages aus. Er löst sich mit blauvioletter Farbe in Wasser und färbt Wolle schwarz.38.9 kg of nitroamidodiphenylamine disulphonic acid are dissolved in water and diazotized with the aid of 6.9 kg of nitrite and 30 kg of hydrochloric acid. The diazo compound, which separates out as a jelly after a short time, is added to the aqueous solution of 14.3 kg of a-naphthylamine and 11 kg of hydrochloric acid. The free mineral acid is then gradually blunted with acetate. After about 12 hours, the amidoazodisulfonic acid has deposited in the form of a dark purple precipitate. This is filtered off and dissolved in water with the addition of the required amount of sodium hydroxide solution. To solve are added at a temperature of about 5 0 C. 7 kg nitrite and 30 kg of hydrochloric acid are added and läfst stand for several hours. The diazoazodisulfonic acid formed is soluble in water and has a blue color. If it is introduced into the solution of 22.4 kg βj-βg-naphthol sulfonic acid, which is kept alkaline with soda, the secondary disazo dye formed separates out in the form of a crystalline precipitate. It dissolves in water with a blue-violet color and dyes wool black.
In analoger Weise erhält man aus dem ß-Naphtol einen intensiven schwarzen Farbstoff, von besonders hervorragender Walkechtheit. Eine sehr gedeckte Nuance färbt die Combination mit Aethyl-a-naphtylamin, die in analoger Weise hergestellt wird.In an analogous way, an intense black dye is obtained from ß-naphtol, of particularly excellent flexing fastness. A very muted shade colors the combination with ethyl-a-naphthylamine, which in analog Way is made.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE116351C true DE116351C (en) |
Family
ID=385708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT116351D Active DE116351C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE116351C (en) |
-
0
- DE DENDAT116351D patent/DE116351C/de active Active
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