DE614838C - Process for the preparation of water-insoluble disazo dyes - Google Patents
Process for the preparation of water-insoluble disazo dyesInfo
- Publication number
- DE614838C DE614838C DEI44277D DEI0044277D DE614838C DE 614838 C DE614838 C DE 614838C DE I44277 D DEI44277 D DE I44277D DE I0044277 D DEI0044277 D DE I0044277D DE 614838 C DE614838 C DE 614838C
- Authority
- DE
- Germany
- Prior art keywords
- water
- preparation
- disazo dyes
- insoluble disazo
- parts
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- WVGKWPSLUCXKHL-UHFFFAOYSA-N bis(4-amino-3-methoxyphenyl)methanone Chemical compound C1=C(N)C(OC)=CC(C(=O)C=2C=C(OC)C(N)=CC=2)=C1 WVGKWPSLUCXKHL-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/033—Disazo dyes characterised by two coupling components of the same type in which the coupling component is an arylamide of an o-hydroxy-carboxylic acid or of a beta-keto-carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Verfahren zur Herstellung von wasserunlöslichen Disazofarbstoffen Es wurde gefunden, daß man wertvolle wasserunlösliche Disazofarbstoffe erhalten kann, wenn man die Tetrazotierungsprodukte aus 4, 4'-Diaminobenzophenon oder dessen Derivaten mit 2, 3-Oxynaphthoesäurearyliden in Gegenwart von wasserlöslichen tertiären organischen Basen kuppelt. Man erhält rote bis blaustichige ote Farbstoffe, die sich durch besondere Reinheit des Farbtons und Unlösliclikeit in Benzin und Kautschuk auszeichnen. Beispiel i 2i,2 Teile 4, 4'-Diaminobenzophenon werden, wie üblich, tetrazotiert. Die erhaltene Lösung läßt man dann in eine Lösung von 53 Teilen 2', 3'-Oxynaphthoylaininobenzol in Pyridin einlaufen. Nach beendeter Kupplung wird der Farbstoff abgesaugt, zuerst mit etwas alkalischem, dann mit reinem Wasser ausgewaschen und getrocknet. Man erhält ein leuchtend rotes Pulver, das infolge seiner Unlöslichkeit in Kautschuk und Vulkanisierechtheit zum Färben von Kautschuk und kautschukähnlichen Massen geeignet ist.Process for the preparation of water-insoluble disazo dyes It has been found that valuable water-insoluble disazo dyes are obtained can, if the tetrazotization products from 4, 4'-diaminobenzophenone or its Derivatives with 2, 3-Oxynaphthoesäurearyliden in the presence of water-soluble tertiary organic bases. Red to bluish ote dyes are obtained which due to the particular purity of the color and its insolubility in petrol and rubber distinguish. Example i 2i, 2 parts of 4, 4'-diaminobenzophenone are, as usual, tetrazotized. The resulting solution is then poured into a solution of 53 parts of 2 ', Run 3'-oxynaphthoylaininobenzene in pyridine. After the coupling is complete, the Dye sucked off, washed out first with a little alkaline, then with pure water and dried. A bright red powder is obtained, owing to its insolubility in rubber and vulcanization fastness for coloring rubber and rubber-like ones Masses is suitable.
Einen ähnlichen Farbstoff erhält man, wenn man als Tetrazokomponente dieTetrazoverbindung aus 4, 4'-Diamino-3; 3'-dichlorbenzoplienon verwendet. -Beispiel 2, 21,2 Teile 4, q.'-Diaminobenzophenon werden tetrazotiert, worauf man das Reaktionsgeinisch in eine Lösung von 64 Teilen i - (2', 3'-Oxynaphthoylamino) -naphthalin in Rohpyridin fließen läßt. Der Farbstoff ist rot und zeigt ähnliche Eigenschaften wie der in Beispiel i beschriebene. Er läßt sich z. B. als Pigmentfarbstoff für Tapeten, Öl- und ('ellulosederivatlacke mit Vorteil verwenden.A similar dye is obtained if the tetrazo compound of 4,4'-diamino-3;3'-dichlorobenzoplienone is used. Example 2, 21.2 parts of 4, q .'-diaminobenzophenone are tetrazotized, whereupon the reaction mixture is allowed to flow into a solution of 64 parts of i - (2 ', 3'-oxynaphthoylamino) naphthalene in crude pyridine. The dye is red and shows properties similar to that described in Example i. He can be z. B. as a pigment for wallpaper, oil and ('use ellulose derivative paints with advantage.
Beispiel 3 21,2 Teile 4, 4'-Diaminobenzophenon werden wie im Beispiel i tetrazotiert und finit 6o Teilen i-(2', 3'-Oxynaphtlioylamino)= 2-methoxybenzol, gelöst in a-Picolin, gekuppelt. Der erhaltene Farbstoff ist etwas blaustichiger rot als der nach Beispiel i erhaltene und besitzt im übrigen die 'gleichen Eigenschaften. Einen noch blaustichigeren Farbstoff erhält man, wenn man das Teträzotierungsprodukt aus 4, 4'-Diamino-3, 3'-dimethoxybenzophenon als Tetrazokomponente verwendet.Example 3 21.2 parts of 4,4'-diaminobenzophenone are as in the example i tetrazotized and finite 6o parts i- (2 ', 3'-Oxynaphtlioylamino) = 2-methoxybenzene, dissolved in a-picoline, coupled. The dye obtained is somewhat more bluish red than that obtained according to example i and otherwise has the same properties. An even more bluish dye is obtained if the Tetrazotation product from 4,4'-diamino-3, 3'-dimethoxybenzophenone used as the tetrazo component.
Beispiel 4 2i,2 Teile 4, 4'-Diaminobenzophenon werden tetrazotiert und mit 72 Teilen des Kondensationsproduktes aus z, 3 - Oxynaphthoesäure und i-Amino-2, 4-dimethoxy-5-chlorbenzol in Pyridin gekuppelt. Man erhält nach dem Trocknen einen sehr blaustichigroten Farbstoff, der sehr gut zum Färben von Kautschuk oder Lacken geeignet ist.Example 4 2i, 2 parts of 4,4'-diaminobenzophenone are tetrazotized and with 72 parts of the condensation product of z, 3 - oxynaphthoic acid and i-amino-2, 4-dimethoxy-5-chlorobenzene coupled in pyridine. After drying, one obtains a very bluish-tinged red dye that is very good for dyeing rubber or paints suitable is.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI44277D DE614838C (en) | 1932-04-22 | 1932-04-22 | Process for the preparation of water-insoluble disazo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI44277D DE614838C (en) | 1932-04-22 | 1932-04-22 | Process for the preparation of water-insoluble disazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE614838C true DE614838C (en) | 1935-06-19 |
Family
ID=7191248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI44277D Expired DE614838C (en) | 1932-04-22 | 1932-04-22 | Process for the preparation of water-insoluble disazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE614838C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2936305A (en) * | 1956-11-29 | 1960-05-10 | Sandoz Ag | Water-insoluble disazo dyestuffs |
-
1932
- 1932-04-22 DE DEI44277D patent/DE614838C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2936305A (en) * | 1956-11-29 | 1960-05-10 | Sandoz Ag | Water-insoluble disazo dyestuffs |
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