DE88848C - - Google Patents
Info
- Publication number
- DE88848C DE88848C DENDAT88848D DE88848DA DE88848C DE 88848 C DE88848 C DE 88848C DE NDAT88848 D DENDAT88848 D DE NDAT88848D DE 88848D A DE88848D A DE 88848DA DE 88848 C DE88848 C DE 88848C
- Authority
- DE
- Germany
- Prior art keywords
- mol
- dye
- blue
- acid
- dyes
- 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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- 150000001875 compounds Chemical class 0.000 claims description 6
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-Diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000002790 naphthalenes Chemical class 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- SSQQBRZUIXIPIP-UHFFFAOYSA-N 5-diazo-2-nitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CCC(=[N+]=[N-])C=C1 SSQQBRZUIXIPIP-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical group NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
- C09B35/52—Tetrazo dyes of the type
-
- 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
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift Nr. 84390 ist ein Verfahren beschrieben zur Herstellung direct färbender Azofarbstoffe, welches darin besteht, dafs man die Tetrazoverbindung des Productes folgender Constitution:In the patent specification no. 84390 a method is described for the production of direct coloring azo-dyes, which consists in using the tetrazo compound of the product of the following constitution:
HO NHHO NH
H2N-H 2 N-
HO3SHO 3 S
mit Aminen, Phenolen etc. combinirt.combined with amines, phenols, etc.
In der Patentschrift Nr. 86199 ist dann gezeigt, dafs ganz allgemein die mittelst 2 Mol. p-Nitranilin und gewisser Naphtalinderivate erhältlichen Producte der allgemeinen Constitution :In the patent specification No. 86199 it is then shown that quite generally the mean 2 moles of p-nitroaniline and certain naphthalene derivatives available products of the general constitution:
Cj0H fi-xjCj 0 H fi-xj
durch Tetrazotiren und darauf folgende Combination mit m-Toluylendiamin oder ß-Naphtol in echte und sehr intensive Farbstoffe übergeführt werden können, deren äufserst werthvolle Eigenschaften darauf zurückzuführen sind, dafs sie den Complex (Naphtalinderivat -f 2 Mol. p-Phenylendiaminrest) enthalten.by Tetrazotiren and subsequent combination with m-toluenediamine or ß-naphthol can be converted into real and very intense dyes, their extremely valuable ones Properties are due to the fact that they contain the complex (naphthalene derivative -f 2 mol. p-phenylenediamine residue).
= N C6 H4 N H, = N C 6 H 4 NH,
SO3HSO 3 H
Bei weiterer Ausbildung dieser Verfahren hat sich, wie in der Patentschrift Nr. 86915 gezeigt ist, ergeben, dafs man Farbstoffe von denselben werthvollen Eigenschaften erhält, wenn man die mit den vorgenannten Producten isomeren Substanzen der allgemeinen Formel:With further development of this method, as in patent specification No. 86915 show that dyes are obtained with the same valuable properties, if one uses the isomeric substances of the general formula:
X YX Y
C6H4 NH2 C 6 H 4 NH 2
N = N-C6H4 NH2 N=N-C6H3 (S O3 H) NH2 N = NC 6 H 4 NH 2 N = NC 6 H 3 (SO 3 H) NH 2
OH(x_y,OH (x _y,
SOsH(x_SO s H (x _
die mittelst 1 Mol. p-Nitranilinsulfosäure und ι Mol. p-Nitranilin aus gewissen Naphtalinderivaten erhalten werden, nach dem Tetrazotiren mit m-Toluylendiamin combinirt.the mean 1 mol. p-Nitranilinsulfonic acid and ι Mol. p-Nitraniline from certain naphthalene derivatives are obtained, after tetrazotization combined with m-toluylenediamine.
So erhält man Farbstoffe von ähnlichen werthvollen Eigenschaften, wenn man an StelleThus one obtains dyes of similar valuable properties, if one takes in place
der in dem Verfahren des Patentes Nr. 86915 benutzten Tetrazoverbindung ausgeht von der Tetrazoverbindung der Substanz nachfolgender Constitution:that in the process of patent No. 86915 Tetrazo compound used starts from the tetrazo compound of the substance below Constitution:
HO3 SHO 3 S
= N-C6H1- NH2 = NC 6 H 1 - NH 2
= N-C6H3 = NC 6 H 3
/SO3H/ SO 3 H
Dieses Product läfst sich herstellen aus P1 ß2-Amidonaphtol-ß3-sulfosäure durch Combination mit je ι Mol. p-Nitrodiazobenzolsulfosäure und p-Nitrodiazobenzol und darauf folgende Reduction.This product can be prepared from P 1 ß 2 -amidonaphthol-ß 3 -sulfonic acid by combining with ι mol. P-nitrodiazobenzenesulfonic acid and p-nitrodiazobenzene and subsequent reduction.
Um aus demselben den neuen Farbstoff herzustellen, verfährt man beispielsweise wie folgt:In order to produce the new dye from the same, one proceeds, for example, as follows:
14 kg des durch obige Formel gekennzeichneten Productes werden mittelst 3,5 kg Nitrit in salzsaurer Lösung in die Tetrazoverbindung übergeführt. Die dunkelblaue Lösung der letzteren läfst man alsdann einlaufen in eine stets alkalisch gehaltene Lösung von 6,1 kg m-Toluylendiamin. Der Farbstoff bildet sich sofort und scheidet sich gröfstentheils als dunkler Niederschlag ab. Nach längerem Stehen wärmt man auf und schlägt den Farbstoff durch Zusatz von Kochsalzlösung nieder; derselbe wird abfiltrirt, geprefst und getrocknet. Der Farbstoff stellt ein metallisch glänzendes Pulver dar, das wenig in kaltem Wasser, leichter in heifsem mit blauer Farbe löslich ist. Aus der wässerigen Lösung wird derselbe von Alkalien ohne Farbenumschlag theilweise gefällt; vollständig schlagen Mineralsäuren die freie Farbsäure in blauschwarzen Flocken nieder. In Alkohol ist der neue Farbstoff unlöslich; derselbe löst sich in concentrirter Schwefelsäure mit grünblauer Farbe, die Lösung wird beim Verdünnen erst violettblau, dann fallen braunviolette Flocken au's; auf ungeheizter Baumwolle erzeugt der Farbstoff im Salz- und Seifenbade intensiv blauschwarze Töne von bemerkenswerther Echtheit.14 kg of the product identified by the above formula becomes 3.5 kg of nitrite on average converted into the tetrazo compound in hydrochloric acid solution. The dark blue solution of the the latter is then allowed to run into a 6.1 kg solution, which is always kept alkaline m-tolylenediamine. The dye is formed immediately and for the most part separates as dark precipitation from. After standing for a long time, warm up and beat the dye down by adding saline solution; it is filtered off, pressed and dried. The dye is a metallic, shiny powder, which is little in cold water, is more easily soluble in hot water with blue color. The aqueous solution becomes the same partly precipitated from alkalis without color change; mineral acids completely beat that free color acid in blue-black flakes. The new dye is insoluble in alcohol; it dissolves in concentrated sulfuric acid with a green-blue color, the solution becomes when diluted first violet-blue, then brown-violet flakes fall; on unheated Cotton, the dye produces intense blue-black tones of in salt and soap baths remarkable authenticity.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE88848C true DE88848C (en) |
Family
ID=360711
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT88848D Active DE88848C (en) |
Country Status (1)
Country | Link |
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DE (1) | DE88848C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5447354A (en) * | 1993-11-10 | 1995-09-05 | Delp; Melvin D. | Children's wagon top conversion assembly |
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0
- DE DENDAT88848D patent/DE88848C/de active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5447354A (en) * | 1993-11-10 | 1995-09-05 | Delp; Melvin D. | Children's wagon top conversion assembly |
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