DE278422C - - Google Patents
Info
- Publication number
- DE278422C DE278422C DENDAT278422D DE278422DA DE278422C DE 278422 C DE278422 C DE 278422C DE NDAT278422 D DENDAT278422 D DE NDAT278422D DE 278422D A DE278422D A DE 278422DA DE 278422 C DE278422 C DE 278422C
- Authority
- DE
- Germany
- Prior art keywords
- acids
- acid
- water
- derivatives
- 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
Links
- -1 aromatic diaminosulfonic acids Chemical class 0.000 claims description 9
- 239000000975 dye Substances 0.000 claims description 6
- 230000000875 corresponding Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 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
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- 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
- 229940044174 4-phenylenediamine Drugs 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22«. GRUPPECLASS 22 «. GROUP
Verfahren zur Darstellung von Entwicklerfarbstoffen.Process for the preparation of developer dyes.
Zusatz zum Patent 273280. Addendum to patent 273280.
Patentiert im Deutschen Reiche vom 29. Juni 1913 ab. Längste Dauer: 7. Januar 1928.Patented in the German Empire on June 29, 1913. Longest duration: January 7, 1928.
Durch das Hauptpatent 273280 ist ein Verfahren zur Darstellung von Entwicklerfarbstoffen geschützt, welches darin besteht, daß man diazotierte Mononitro- oder Acidylaminoarylacidylderivate aromatischer Diaminsulfosäuren mit den aus aromatischen Aminothiazolderivaten erhältlichen Pyrazolonen oder Pyrazoloncarbonsäuren kuppelt und die Nitrogruppe reduziert bzw. den Acidylaminorest verseift.The main patent 273280 is a method for the preparation of developer dyes protected, which consists in the fact that one diazotized mononitro or acidylaminoarylacidyl derivatives aromatic diaminesulfonic acids with the pyrazolones obtainable from aromatic aminothiazole derivatives or Pyrazoloncarboxylic acids couple and reduce the nitro group or the acidylamino radical saponified.
Es wurde nun gefunden, daß man zu neuen wertvollen Farbstoffen gelangt, wenn man die gemäß dem Hauptpatente verwendeten Nitro- oder Acidylaminoderivate aromatischer Diaminsulfosäuren hier durch die entsprechenden Derivate von Diamincarbonsäuren ersetzt.It has now been found that new valuable dyes can be obtained if the according to the main patent used nitro or acidylamino derivatives of aromatic diamine sulfonic acids replaced here by the corresponding derivatives of diamine carboxylic acids.
301 Teile 4-m-Nitrobenzoyl-i · 4-phenylendiamin-2-carbonsäure (erhältlich durch Kondensation von ι - Acetyl -1 · 4 - phenylendiamin - 2-carbonsäure mit m-Nitrobenzoylchlorid und Abspaltung der Acetylgruppe als farblose, in Wasser, Säuren und Alkalien leicht lösliche Substanz, die aus essigsaurer Lösung durch Aussalzen wiedergewonnen wird) werden mit 67 Teilen Natriumnitrit und Salzsäure diazotiert (die farblose Diazoverbindung ist leicht löslich) und mit 404 Teilen i-Dehydrothiotolyl-4-methyl-5-pyrazolonsulfosäure in sodaalkalischer Lösung gekuppelt. Nach Beendigung der Kupplung werden 450 Teile kristallisiertes Schwefelnatrium zugegeben und aufgekocht. Der in Lösung gegangene reduzierte Farbstoff wird ausgesalzen, filtriert und getrocknet. Er löst sich leicht in Wasser, färbt Baumwolle gelb an und geht, auf der Faser diazotiert und mit ß-Naphtol entwickelt, in ein waschechtes rotstichiges Gelb über. Statt der Nitrobenzoyl - ρ - phenylendiamincarbonsäure kann man entsprechende Derivate der 3 · 5-Diaminobenzoesäure, Diaminodiarylcarbonsäuren und anderer verwenden.301 parts of 4-m-nitrobenzoyl-i.4-phenylenediamine-2-carboxylic acid (obtainable by condensation of ι - acetyl -1 · 4 - phenylenediamine - 2-carboxylic acid with m-nitrobenzoyl chloride and cleavage of the acetyl group as a colorless, in Water, acids and alkalis easily soluble substance, which by acetic acid solution through Salting out is recovered) are diazotized with 67 parts of sodium nitrite and hydrochloric acid (the colorless diazo compound is easily soluble) and with 404 parts of i-dehydrothiotolyl-4-methyl-5-pyrazolone sulfonic acid coupled in a soda-alkaline solution. After the coupling has ended, 450 parts are crystallized Sulfur sodium added and boiled. The reduced dye that went into solution is salted out, filtered and dried. It dissolves easily in water, dyes cotton turns yellow and, diazotized on the fiber and developed with ß-naphtol, turns into a real one reddish yellow over. Instead of nitrobenzoyl - ρ - phenylenediamine carboxylic acid can corresponding derivatives of 3 · 5-diaminobenzoic acid, diaminodiarylcarboxylic acids and other use.
Das Nitrobenzoylderivat der 3 · 5-Diäminobenzoesäure ist farblos und in Wasser, besonders bei Gegenwart von Alkalien oder Mineralsäuren, leicht löslich; es wird aus essigsaurer Lösung durch Kochsalz ausgesalzen. Die Diazoverbindung ist in Wasser leicht löslieh. Das Mononitrobenzoylderivat der 4 · 4'-Diaminodiphenyl-3 · 3'-dicarbonsäure, durch Umsetzung der Dicarbonsäure mit einem Molekül Nitrobenzoylchlorid bei gewöhnlicher Temperatur erhältlich, ist alkalisch leicht löslieh, wird aber durch Säuren, auch durch Mineralsäuren, ausgefällt. Es ist meist durch Oxydationsprodukte schwach grüngrau gefärbt. Die gelb gefärbte Diazoverbindung ist in Wasser schwer löslich. Die Substanzen habenThe nitrobenzoyl derivative of 3 · 5-dieminobenzoic acid is colorless and especially in water easily soluble in the presence of alkalis or mineral acids; it becomes acetic acid Salt out the solution with table salt. The diazo compound is easily soluble in water. The mononitrobenzoyl derivative of 4x4'-diaminodiphenyl-3x3'-dicarboxylic acid Reaction of the dicarboxylic acid with a molecule of nitrobenzoyl chloride at ordinary Temperature available, is easily soluble in alkaline, but is by acids, also by Mineral acids, precipitated. It is mostly colored pale green-gray by oxidation products. The yellow colored diazo compound is sparingly soluble in water. The substances have
keinen Schmelzpunkt, sondern zersetzen sich bei höherer Temperatur.no melting point, but decompose at a higher temperature.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE278422C true DE278422C (en) |
Family
ID=534427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT278422D Active DE278422C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE278422C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3117117A (en) * | 1959-09-16 | 1964-01-07 | Ici Ltd | Dyestuffs capable of reaction with textile fibers having acylatable hydrogen atoms |
| WO2004018414A2 (en) * | 2002-08-23 | 2004-03-04 | Pharmacia & Upjohn Company Llc | Antibacterial agents |
-
0
- DE DENDAT278422D patent/DE278422C/de active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3117117A (en) * | 1959-09-16 | 1964-01-07 | Ici Ltd | Dyestuffs capable of reaction with textile fibers having acylatable hydrogen atoms |
| WO2004018414A2 (en) * | 2002-08-23 | 2004-03-04 | Pharmacia & Upjohn Company Llc | Antibacterial agents |
| WO2004018414A3 (en) * | 2002-08-23 | 2004-06-17 | Upjohn Co | Antibacterial agents |
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