DE273280C - - Google Patents
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- Publication number
- DE273280C DE273280C DENDAT273280D DE273280DA DE273280C DE 273280 C DE273280 C DE 273280C DE NDAT273280 D DENDAT273280 D DE NDAT273280D DE 273280D A DE273280D A DE 273280DA DE 273280 C DE273280 C DE 273280C
- Authority
- DE
- Germany
- Prior art keywords
- acids
- derivatives
- aromatic
- acid
- instead
- 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.)
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- 239000002253 acid Substances 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 7
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 6
- -1 aromatic aminothiazole derivatives Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000001808 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 241000490025 Schefflera digitata Species 0.000 claims 1
- 229940051880 analgesics and antipyretics Pyrazolones Drugs 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXUQTDZNOHRWLI-QOPOCTTISA-O Primulin Natural products O(C)c1c(O)c(OC)cc(-c2c(O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O3)cc3c(O)cc(O)cc3[o+]2)c1 PXUQTDZNOHRWLI-QOPOCTTISA-O 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 229940083761 high-ceiling diuretics Pyrazolone derivatives Drugs 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(E)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 1
- PKTAIAYSUXBPPN-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)N(C1=CC=C(C=C1)N)[N+](=O)[O-] Chemical compound C(C1=CC=CC=C1)(=O)N(C1=CC=C(C=C1)N)[N+](=O)[O-] PKTAIAYSUXBPPN-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- BTXCHYCUHBGRMK-UHFFFAOYSA-N amino sulfamate Chemical compound NOS(N)(=O)=O BTXCHYCUHBGRMK-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000003973 paint 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000001043 yellow dye Substances 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)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVe 273280 KLASSE 22«. GRUPPE- JVe 273280 CLASS 22 «. GROUP
FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. CÖLN a. Rh.FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. CÖLN a. Rh.
Verfahren zur Darstellung von Entwicklerfarbstoffen. Patentiert im Deutschen Reiche vom 8. Januar 1913 ab.Process for the preparation of developer dyes. Patented in the German Empire on January 8, 1913.
Wenn man m-Nitrobenzoyl-p-phenylendiaminsulfosäure diazotiert, mit dem aus der Dehydrothiotoluidinsulfosäure nach üblicher Methode erhältlichen Pyrazolon kuppelt und die Nitrogruppe in üblicher Weise reduziert, so erhält man einen gelben Farbstoff, der sich durch vorzügliche Affinität zur Baumwollfaser auszeichnet, und dessen Färbung nach Diazotierung und Entwicklung mit ß-NaphtolIf you have m-nitrobenzoyl-p-phenylenediaminesulfonic acid diazotized, coupled with the pyrazolone obtainable from the dehydrothiotoluidinsulfonic acid by a conventional method and the Reduced nitro group in the usual way, a yellow dye is obtained, which characterized by an excellent affinity for cotton fibers, and its coloration Diazotization and development with ß-naphtol
ίο ein rotstichiges Gelb liefert.ίο delivers a reddish yellow.
Dieses Resultat ist von technischer Bedeutung, da derartig gelbe Nuancen durch Entwicklung auf der Faser mit ß-Naphtol bisher nicht zugänglich waren.This result is of technical importance because such yellow nuances are caused by development were previously inaccessible on the fiber with ß-naphtol.
Statt der Nitrobenzoyl-p-phenylendiamin- -sulfosäure können beliebige andere Nitroarylacidylderivate aromatischer Diaminsulfosäuren, statt des Pyrazolone aus der Dehydrothiotoluidinsulfosäure Pyrazolonderivate anderer aromatischer Thiazolderivate verwendet werden. Instead of the nitrobenzoyl-p-phenylenediamine -sulfonic acid can be any other nitroarylacidyl derivatives of aromatic diaminesulfonic acids, instead of the pyrazolone from the dehydrothiotoluidinsulfonic acid pyrazolone derivatives of others aromatic thiazole derivatives can be used.
337 Teile m-Nitrobenzoyl-p-phenylendiaminsulfosäure werden mit 69 Teilen Natriumnitrit und Salzsäure diazotiert und mit 404 Teilen i-Dehydrothiotolyl - 3 - methyl- 5 -pyrazolonsulfosäure in sodaalkalischer Lösung vereinigt. Dann werden 450 Teile kristallisiertes Schwefelnatrium zugegeben; es wird aufgekocht und nach Lösung der Farbstoff durch Zugeben von Kochsalz ausgesalzen, filtriert und getrocknet. Er zieht mit gelber Farbe auf Baumwolle. Die diazotierte Färbung liefert bei der Entwicklung mit ß-Naphtol ein waschechtes rotstichiges Gelb.337 parts of m-nitrobenzoyl-p-phenylenediaminesulfonic acid are diazotized with 69 parts of sodium nitrite and hydrochloric acid and with 404 Share i-dehydrothiotolyl-3-methyl-5-pyrazolone sulfonic acid combined in soda-alkaline solution. Then 450 parts of crystallized sodium sulphide are added; it is boiled and after dissolving the dye, salted out by adding common salt, filtered and dried. He draws with yellow paint on cotton. The diazotized color results in development with ß-naphtol real reddish yellow.
Statt der Nitrobenzoyl-p-phenylendiaminsulfosäure kann man allgemein Mononitroarylacidylderivate aromatischer Diaminsulfosäuren, z. B. 4 · 4'-Diaminodiphenyl-3 · 3'-disulfosäure, 4 · 4' - Diaminodiphenylharnstoff-3 · 3' - disulfosäure, Diaminostilbendisulfosäure, 2 · 6 - Toluylendiamino - 4 - sulfosäure verwenden. Man erhält sie durch Kondensation von z. B. einem Molekül Nitrobenzoylchlorid mit einem Molekül der entsprechenden Diaminosulfosäure in alkalischer bzw. essigsaurer Lösung. Ihre zum Teil gelb gefärbten Natriumsalze sind in heißem Wasser leicht, in kaltem Wasser schwer löslich. Die freien Säuren sind in Wasser unlöslich. Sie lassen, sich in üblicher Weise diazotieren und mit Azokomponenten kuppeln.Instead of nitrobenzoyl-p-phenylenediaminesulfonic acid one can generally mononitroarylacidyl derivatives of aromatic diaminesulfonic acids, e.g. B. 4x4'-diaminodiphenyl-3x3'-disulfonic acid, 4 4 '- diaminodiphenylurea 3 3' - disulfonic acid, diaminostilbene disulfonic acid, Use 2 · 6 - toluenediamino - 4 - sulfonic acid. They are obtained through condensation from Z. B. one molecule of nitrobenzoyl chloride with one molecule of the corresponding diaminosulfonic acid in alkaline or acetic acid solution. Their sodium salts, some of which are yellow in color, are light in hot water, Slightly soluble in cold water. The free acids are insoluble in water. You let Diazotize in the usual way and couple with azo components.
Statt des Pyrazolons aus der Dehydrothiotoluidinsulfosäure können diejenigen aus der Primulinsulfosäure, aus der Aminophenyli · 2-naphtothiazol-7-sulfosäure und anderen aromatischen Aminothiazolderivaten verwendet werden. Diese Pyrazolonderivate werden in der üblichen Weise durch Reduktion der entsprechenden Diazoverbindungen zu Hydrazinen und Kondensation derselben mit Acetessigester bzw. Oxalessigester erhalten. Sie sind als freie Säuren gelb gefärbt und vereinigenInstead of the pyrazolone from the dehydrothiotoluidinsulfonic acid, those from the primulin sulfonic acid, from the aminophenyli · 2-naphtothiazole-7-sulfonic acid and others aromatic aminothiazole derivatives can be used. These pyrazolone derivatives are in the usual way by reducing the corresponding diazo compounds to hydrazines and condensation of the same with acetoacetic ester or oxaloacetic ester. they are colored yellow as free acids and combine
Claims (1)
Verfahren zur Darstellung von Entwicklerfarbstoffen, darin bestehend, daß man diazotierte Mononitro- oder Acidylaminoarylacidylderivate aromatischer Diaminsulfosäiiren mit den aus aromatischen Aminothiazolderivaten erhältlichen Pyrazolonen oderPyrazoloncarbonsäuren kuppelt und die Nitrogruppe reduziert bzw. den Acidylaminorest verseift.Pate ν τ-Α ν SPEU c η:
Process for the preparation of developer dyes, which consists in coupling diazotized mononitro or acidylaminoarylacidyl derivatives of aromatic diaminesulfonic acids with the pyrazolones or pyrazolonecarboxylic acids obtainable from aromatic aminothiazole derivatives and reducing the nitro group or saponifying the acidylamino radical.
Publications (1)
Publication Number | Publication Date |
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DE273280C true DE273280C (en) |
Family
ID=529747
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT273280D Active DE273280C (en) |
Country Status (1)
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DE (1) | DE273280C (en) |
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