DE297414C - - Google Patents
Info
- Publication number
- DE297414C DE297414C DENDAT297414D DE297414DA DE297414C DE 297414 C DE297414 C DE 297414C DE NDAT297414 D DENDAT297414 D DE NDAT297414D DE 297414D A DE297414D A DE 297414DA DE 297414 C DE297414 C DE 297414C
- Authority
- DE
- Germany
- Prior art keywords
- oxynaphthalene
- derivatives
- substituted
- benzoyl radical
- benzoylethylamino
- 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
- 239000000975 dye Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000001808 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 241000947840 Alteromonadales Species 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 297414 KLASSE 22 a. GRUPPE- M 297414 CLASS 22 a. GROUP
Monoazofarbstoffe^Monoazo dyes ^
Zusatz zum Patent 296991.Addendum to patent 296991.
Patentiert im Deutschen Reiche vom 4. September 1914 ab. Längste Dauer: 6. August 1929.Patented in the German Empire on September 4, 1914. Longest duration: August 6, 1929.
Durch das Hauptpatent 296991 ist ein Verfahren zur Darstellung von zur Herstellung von Pigmentfarben geeigneten Monoazofarbstoffen geschützt, darin bestehend, daß man die Diazoverbindung des i-Aminoanthrachinons miti-Benzo ylamino-7-oxynaphtalin oder dessen im Benzoylrest substituierten Derivaten, mit oder ohne Zusatz von Türkischrotöl oder ähnlich wirkenden Mitteln, in Gegenwart oder Abwesenheit von Substraten, kuppelt.By the main patent 296991 is a method for the representation of for the production Protected by pigment dyes suitable monoazo dyes, consisting in that the diazo compound of i-aminoanthraquinone miti-Benzo ylamino-7-oxynaphthalene or its derivatives substituted in the benzoyl radical, with or without the addition of Turkish red oil or similarly acting agents, in the presence or absence of substrates, couples.
Es hat sich nun weiter gezeigt, daß sich auch die N-Alkylderivate des i-Benzoylamino-7-oxynaphtalins oder dessen im Benzoylrest substituierten Derivaten in ausgezeichneterIt has now been shown that the N-alkyl derivatives of i-benzoylamino-7-oxynaphthalene are also found or its derivatives substituted in the benzoyl radical in excellent
1S Weise zur Herstellung solcher Pigmentazofarbstoffe eignen. 1 S manner for the production of such pigment azo dyes are suitable.
Die genannten Derivate des i-Benzoylamino-7-oxynaphtalins können z. B. durch Einwirkung der ι Mol. entsprechenden Menge von Benzoylchlorid oder dessen Substitutionsprodukten auf die i-Alkylamino-7-oxynaphtaline, die ihrerseits z. B. durch Alkalischmelze der entsprechenden i-Monoalkylaminonaphtalin-7-sulfosäuren erhältlich sind, in Gegenwart eines indifferenten Lösungsmittels und in Ab- oder Anwesenheit von salzsäurebindenden Mitteln dargestellt werden. Sie bilden in reinem Zustande farblose kristallinische Körper, die in Wasser sehr schwer, in Ätzalkalien dagegen leicht löslich sind. Sie können aus organischen Lösungsmitteln, z. B. aus Alkohol umkristallisiert werden. Das i-Benzoyläthylamino-7-oxynaphtalin schmilzt bei etwa 224 bis 225°, das i-Benzoylmethylamino-7-oxynaphtalin bei etwa 186 bis 187 °, das 1 · 2'-Chlorbenzoyläthylamino-7-oxynaphtalin bei etwa 232 bis 233 °.The mentioned derivatives of i-benzoylamino-7-oxynaphthalene can e.g. B. by the action of ι Mol. Corresponding amount of Benzoyl chloride or its substitution products on the i-alkylamino-7-oxynaphthalenes, which in turn z. B. by alkali melting of the corresponding i-monoalkylaminonaphthalene-7-sulfonic acids are available in the presence of an inert solvent and in off or Presence of hydrochloric acid binding agents are shown. They form in a pure state colorless crystalline bodies, which are very difficult in water, but in caustic alkalis are easily soluble. You can from organic solvents, e.g. B. recrystallized from alcohol will. I-Benzoylethylamino-7-oxynaphthalene melts at about 224 to 225 °, the i-benzoylmethylamino-7-oxynaphthalene at about 186 to 187 °, the 1 · 2'-chlorobenzoylethylamino-7-oxynaphthalene at about 232 to 233 °.
22,3 Teile i-Aminoanthrachinon werden in ■ bekannter Weise in konzentrierter Schwefelsäure diazotiert. Das wie üblich isolierte Diazoniumsulfat wird in Wasser gelöst und in eine mit überschüssigem Acetat versetzte Lösung von 33 Teilen 1 · 2'-Chlorbenzoyläthylaminö-7-oxynaphtalin in Wasser und der nötigen Menge Natronlauge einlaufen gelassen. Nach beendeter Kuppelung wird der Farbstoff filtriert, ausgewaschen und in Pastenform gebracht oder getrocknet. Die Kuppelung kann auch in alkalischer Lösung sowie in Gegenwart von Türkischrotöl oder ähnlich wirkenden Mitteln vorgenommen werden. Ferner können die bei der Pigmentfarbenherstellung üblichen Substrate schon bei der Farbstoffdarstellung zugesetzt werden.22.3 parts of i-aminoanthraquinone are in a known manner in concentrated sulfuric acid diazotized. The diazonium sulfate isolated as usual is dissolved in water and in a solution of 33 parts of 1 · 2'-Chlorbenzoyläthylaminö-7-oxynaphtalin mixed with excess acetate run in water and the necessary amount of sodium hydroxide solution. When the coupling is complete, the dye will filtered, washed out and pasted or dried. The coupling can also in an alkaline solution as well as in the presence of Turkish red oil or similar effects Funds are made. Furthermore, the customary in pigment paint production can be used Substrates are added during the preparation of the dye.
In analoger Weise verfährt man, wenn man statt des 1 ·^'-Chlorbenzoyläthylamino^-oxynaphtalins andere im Benzoylrest substituierte Derivate des i-Benzoyläthylamino-7-oxynaphtalins verwendet.The procedure is analogous if, instead of the 1 · ^ '- chlorobenzoylethylamino ^ -oxynaphthalene other derivatives of i-benzoylethylamino-7-oxynaphthalene substituted in the benzoyl radical used.
Die wässerige Lösung des aus 22,3 Teilen I-Aminoanthrachinon erhaltenen Diazoniumsulfats wird in eine mit überschüssigem Acetat versetzte Lösung von 30 Teilen i-Benzoyläthylamino-7-oxynaphtalin in Wasser und der nötigen Menge Natronlauge einlaufen gelassen. Nach beendeter Kuppelung wird der Farbstoff abfiltriert, ausgewaschen und in Pastenform gebracht oder getrocknet.The aqueous solution of the diazonium sulfate obtained from 22.3 parts of I-aminoanthraquinone is in a mixed with excess acetate solution of 30 parts of i-benzoylethylamino-7-oxynaphthalene run in water and the necessary amount of sodium hydroxide solution. When the coupling is complete, the dye will filtered off, washed out and put into paste form or dried.
In analoger Weise verfährt man, wenn man das i-Benzoyläthylamino-7-oxynaphtalin durch andere 1 - Benzoylalkylamino - 7 - oxynaphtaline oder deren im Benzoylrest substituierten Derivate ersetzt.The procedure is analogous if the i-benzoylethylamino-7-oxynaphthalene is through other 1-benzoylalkylamino-7-oxynaphthalines or their derivatives substituted in the benzoyl radical replaced.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE297414C true DE297414C (en) |
Family
ID=551713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT297414D Active DE297414C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE297414C (en) |
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0
- DE DENDAT297414D patent/DE297414C/de active Active
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