DE423394C - Process for the preparation of azo dyes - Google Patents
Process for the preparation of azo dyesInfo
- Publication number
- DE423394C DE423394C DEF55415D DEF0055415D DE423394C DE 423394 C DE423394 C DE 423394C DE F55415 D DEF55415 D DE F55415D DE F0055415 D DEF0055415 D DE F0055415D DE 423394 C DE423394 C DE 423394C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- azo dyes
- preparation
- acid
- nitrite
- 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
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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Description
Verfahren zur Darstellung von Azofarbstoffen. Es wurde gefunden, daß man wertvolle rote über violette bis schwarze Azofarbstoffe von vorzüglicher Lichtechtheit und guter Bäuchechtheit erhält, wenn man die Diazoverbindungen aromatischer Amine einwirken läßt auf Kondensationsprodukte von Mono-oder Diaminocarbazolen, deren Homologen und Substitutionsprodukten mit i oder 2 Mol. ß-Oxynaphthoesäure und deren Substitutionsprodukten, in denen die Orthostellung zur Hydroxylgruppe unbesetzt ist. Die erhaltenen Azofarbstoffe können sowohl in Substanz als auch auf Substraten, z. B. für Lackzweike oder auf der Faser in der Art der Eisfarben, erzeugt werden.Process for the preparation of azo dyes. It was found that valuable red to purple to black azo dyes of excellent lightfastness and good stomach fastness is obtained when using the diazo compounds of aromatic amines can act on condensation products of mono- or diaminocarbazoles, their Homologues and substitution products with 1 or 2 mol. Ss-Oxynaphthoic acid and their Substitution products in which the ortho position to the hydroxyl group is unoccupied is. The azo dyes obtained can be used both in substance and on substrates, z. B. for paint doubles or on the fiber in the manner of ice colors are generated.
Die Herstellung der Carbazylide der fl-Oxynaphthoesäure geschieht in der gleichen Weise wie die der bekannten ß-Oxynaphthoesätirearylide.The carbazylides of fl-oxynaphthoic acid are produced in the same way as that of the known ß-oxynaphthoesätirearylide.
B e i s p i e 1 e.A t s p e 1 e.
1. 13,8 Teile p-Nitranilin werden mit 36 Teilen Salzsäure von :2o' B# und 7 Teilen Nitrit diazotiert und unter Kühlung einlaufen gelassen in eine Lösung von 35,2 Teilen des Kondensationsproduktes aus 18,8 Teilen ß-Oxynaphthoesäure und i8,2Teilen 3-Aminocarbazol in 14 Teilen Ätznatron und 3000 Teilen Wasser. Die Abscheidung des roten Farbstoffes beginnt sofort. Man rührt einige Zeit nach, filtriert und trocknet. 2. I8,4TeileBenzidinwerdenrnit6oTeilen Salzsäure von 2o'B# und 14Teilen Nitrit diazotiert und unter Kühlung einlaufen gelassen in eine Lösung von 92, Teilen des Kondensationsproduktes aus 37,6 Teilen ß-Oxynaphthoesäure und 65, 1 Teilen 3 - Amino-6-Brom-N-Äthylcarbazol, FP- 248', in :24 Teilen Ätznatron und 8ooo Teilen Wasser. Die Abscheidung des violetten Farbstoffes beginnt sofort. Man rührt einige Zeit nach, filtriert und, trocknet. 1. 13.8 parts of p-nitroaniline are diazotized with 36 parts of hydrochloric acid from: 2o 'B # and 7 parts of nitrite and allowed to run, with cooling, into a solution of 35.2 parts of the condensation product of 18.8 parts of β-oxynaphthoic acid and 18, 2 parts of 3-aminocarbazole in 14 parts of caustic soda and 3000 parts of water. The separation of the red dye begins immediately. The mixture is stirred for some time, filtered and dried. Diazotized 2 I8,4TeileBenzidinwerdenrnit6oTeilen hydrochloric acid of # and 2o'B 14Teilen nitrite under cooling and allowed the condensation product of 37.6 parts enter beta-hydroxynaphthoic acid and 65 in a solution of 92 parts, 1 parts of 3 - amino-6-bromo-N -Ethylcarbazole, FP- 248 ', in: 24 parts of caustic soda and 8,000 parts of water. The separation of the violet dye begins immediately. The mixture is stirred for some time, filtered and dried.
3. G r u n d i e r u n g: Kondensationsprodukt aus i Mol. ß-Oxynaphthoesäure mit 1 MOI- 3-Aminocarbazol, Fp. 313 -bis 314'. 13,5 9 lösen in 40 ccm Natronlauge, 34' B#, 30 ccm NatrontürkischrotGl, 5o Prozent, mit heißem Wasser auf 1 1 stellen. 3. G run d c ycle. Condensation product of i mol ß-oxynaphthoic acid with 1 MOI 3-aminocarbazole, mp 313 bis 314 '.. Dissolve 1 3.5 9 in 40 ccm sodium hydroxide solution, 34 'B #, 30 ccm sodium turkish red glass, 5o percent, set to 1 1 with hot water.
Ausfärben in p-Arninophenylazo-cx-naphthylamin: 2,62 9, 5,2 ccm Salzsäure, 2-2,' B#, 1,44 g Nitrit, auf 1 1 stellen, neutralisieren Ulit 4 9 essigsaurem Natron.Coloring in p-aminophenylazo-cx-naphthylamine: 2.62 cc, 5.2 cc hydrochloric acid, 2-2, 'B #, 1.44 g nitrite, set to 1 1 , neutralize ulit 4 9 acetic acid soda.
4. G r u n d i e r u n g: Kondensationsprodukt aus :2 Mol. ß-Oxynaphthoesäure mit I MOI. 3,6-Diaminocarbazol, Fp. über 300'. io,2 g lösen in 30 cem Natronlauge, 34' B#, 30 ccm Na-Urontürkischrotöl, 50 Prozent, mit heißem Wasser auf 1 1 stellen.4. G run d c ycle: condensation product of:. 2 moles of beta-oxynaphthoic acid with I MOI. 3,6-diaminocarbazole, m.p. over 300 '. 10, 2 g dissolve in 30 cem sodium hydroxide solution, 34 'B #, 30 ccm Na uron turkish red oil, 50 percent, set to 1 1 with hot water.
Ausfärben in p-Aminophenylazo-a-naphthviamin - 2-,62 g, 5,2, ccm Salzsäure, 22,' B#, 1,-t4 g Nitrit, auf 1 1 stellen, neutralisieren mit 4 g essigsaurem Natron. 5. G r u n d i e r u n g: Kondensationsprodukt aus i Mol. ß-Oxynaphthoesäure mit i Mol. 3-Arninocarbazol, 13,5 9 lösen in 4o ccm Natronlauge, 34' B#, 30 ccm Natrontürkischrotöl, 50 Prozent, mit heißem Wasser auf 1 1 stellen.Discolouring in p-aminophenylazo-a-naphthviamin - 2, 62 g, 5.2 cc of hydrochloric acid, 22, 'B # 1, -T4 g nitrite at 1 1 represent, neutralize with 4 g of sodium acetate. 5. G run d c ycle. Condensation product of beta-oxynaphthoic acid with i Mol i mole of 3-Arninocarbazol, 13.5 9 dissolved in 4o cc of sodium hydroxide solution, 34 'B #, 30 cc Natrontürkischrotöl, 50 percent, with hot water to 1. 1 set.
A,usfärben in einer Diazolösung aus: 2-,gi o - Phenetidinazo - a - naphthylamin, 2,6 ccm Salzsäure, 2,2.0 B#, 0,72 g Nitrit, auf 1 1 stellen, neutralisieren mit .2 g essigsaurem Natrium.Color in a diazo solution from: 2-, gi o - phenetidinazo -a- naphthylamine, 2.6 cc hydrochloric acid, 2.2.0 B #, 0.72 g nitrite, set to 1 1 , neutralize with .2 g acetic acid sodium.
6. Grundi erun g genau wie bei Beispiel 5. 6. Grundi chan g just as in Example 5. FIG.
Ausfärben in einer Diazolösung aus: 2,75 9 m - Arninobenzaldehydazo - a - naphthylarnin, :2,6 ccm Salzsäure, :22' B#, 0,72 9 Nitrit, auf 1 1 stellen, neutralisieren mit 2 g essigsaurem Natrium.Color in a diazo solution from: 2.75 9 m - aminobenzaldehyde azo - a - naphthylamine,: 2.6 ccm hydrochloric acid,: 22 'B #, 0.72 9 nitrite, set to 1 1 , neutralize with 2 g sodium acetic acid.
7. G r u n d i e r u n g: Kondensationsprodukt aus 2 Mol. ß-Oxynaphthoesäure mit I MOI- 3-6-Diaminocarbazol. io,2 g lösen in 30 ccm Natronlauge, 34' B#, 30 ccm, Türkischrotöt" 5o Prozent, mit heißem Wasser auf 1 1 stellen. 7. G run d c ycle: condensation product of 2 moles of beta-oxynaphthoic acid with I MOI 3-6-diaminocarbazole.. 10, 2 g dissolve in 30 cc sodium hydroxide solution, 34 'B #, 30 cc, Turkish red pot "5o percent, set to 1 1 with hot water.
Ausfärben in einer Diazolösung aus: 5,8-9 g o - Phenetidinazo - a - naphthylamil-1, 5,2, ccni Salzsäure, 220 B#, 1,44 g Nitrit, auf 2, 1 stellen, neutralisieren mit 4 g essigsaurem Natrium. 8. Grundierung genau wie bei Beispiel 7. Discolouring in a diazo solution from: 5.8 to 9 g o - Phenetidinazo - a - naphthylamil-1, 5,2, cc of hydrochloric acid, 220 B #, 1.44 g nitrite, set to 2, 1, neutralizing with 4 g of sodium acetate . 8. Primer exactly as in example 7.
Ausfärben in einer DiazolÖsung aus: 5,5 g m - -#%,minobenzaldehydazo - a - naphthvlamin, 5,2 ccm Salzsäure, 22' B#, 444 9 Nitrit, auf :2 1 stellen, neutralisieren mit 4 9 essigsaurem Natrium.Color in a diazole solution from: 5.5 g m - - #%, minobenzaldehydazo - a - naphthvlamin, 5.2 ccm hydrochloric acid, 22 'B #, 444 9 nitrite, set to: 2 1 , neutralize with 4 9 sodium acetic acid.
Das. abgekochte, getrocknete Baumwollgarn wird mit der Naphtholgrundierung gut imprägniert, hierauf abgewunden und ohne getrocknet zu werden in dem betreffenden Diazobad ausgefärbt, dann wird kalt gewaschen, durch ein 5o' C warmes Sodabad genommen (?- g Soda katziniert im Liter), wieder kalt gewaschen und getrocknet.That. Boiled, dried cotton yarn is well impregnated with the naphthol primer, then unwound and dyed in the relevant diazo bath without being dried, then washed cold, taken in a 5o C warm soda bath (? - g soda catinated per liter), washed cold again and dried.
Man erhält tiefe Schwarz von sehr guten Echtheitseigenschaften.Deep blacks with very good fastness properties are obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF55415D DE423394C (en) | 1924-02-09 | 1924-02-09 | Process for the preparation of azo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF55415D DE423394C (en) | 1924-02-09 | 1924-02-09 | Process for the preparation of azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE423394C true DE423394C (en) | 1926-01-04 |
Family
ID=7107669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF55415D Expired DE423394C (en) | 1924-02-09 | 1924-02-09 | Process for the preparation of azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE423394C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2110413A1 (en) * | 2007-02-14 | 2009-10-21 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Dispersing agent for organic pigment and use thereof |
-
1924
- 1924-02-09 DE DEF55415D patent/DE423394C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2110413A1 (en) * | 2007-02-14 | 2009-10-21 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Dispersing agent for organic pigment and use thereof |
| EP2110413A4 (en) * | 2007-02-14 | 2011-03-02 | Dainichiseika Color Chem | Dispersing agent for organic pigment and use thereof |
| US7993446B2 (en) | 2007-02-14 | 2011-08-09 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Dispersing agent for organic pigment and use thereof |
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