CH165038A - Process for the preparation of a black azo dye. - Google Patents
Process for the preparation of a black azo dye.Info
- Publication number
- CH165038A CH165038A CH165038DA CH165038A CH 165038 A CH165038 A CH 165038A CH 165038D A CH165038D A CH 165038DA CH 165038 A CH165038 A CH 165038A
- Authority
- CH
- Switzerland
- Prior art keywords
- black
- dye
- azo dye
- coupled
- amino
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 3
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 claims description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 239000004552 water soluble powder Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 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
- C09B35/50—Tetrazo dyes
- C09B35/60—Tetrazo dyes of the type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 150006. Verfahren zur Herstellung eines schwarzen Azofarbstoffes. Vorliegendes Patent bezieht sich auf ein Verfahren zur Herstellung eines schwarzen Azofarbstoffes, dadurch gekennzeichnet, dass man p-Nitranilin dianotiert und in saurer Lösung mit 1-Amino-8-naphthol-4.6-disulfo- säure kuppelt, den Monoazofarbstoff in al kalischer Lösung mit dianotiertem 5-Nitro- 2-amino-l-anisol kuppelt, den Disazofarbstoff reduziert,
tetrazotiert und mit 1 Mol m-Phe- nylendiamin und 1 Mol 3.5-Diaminobenzoe- säure kuppelt.
Der so erhaltene Farbstoff ist ein schwar zes, wasserlösliches Pulver und färbt Baum wolle in schwarzen Tönen, die durch Nach behandlung mit Formaldehyd und Kupfer salzen wasch- und lichtecht werden.
<I>Beispiel:</I> 13,8 kg p-Nitranilin werden in üblicher Weise dianotiert und in saurem Medium mit 31,9 kg 1-Amirro-8-naphthol-4.6-disrrlfosäure gekuppelt. Der erhaltene Monoazofarbstoff wird in sodaalkalischer Lösung mit einer aus 17,2 kg 5-Nitro-2-amino-l-anisol bereite ten Diazolösung weitergekuppelt und der isolierte Disazofarbstoff mit einer Lösung von 72 kg kristallisiertem Schwefelnatrium reduziert.
Der abgeschiedene Farbstoff wird mit Wasser angeteigt und unter Kühlung mit einer wässerigen Lösung von 14 kg Natriumnitrit und überschüssiger Salzsäure versetzt. Die so erhaltene Tetrazosuspension wird unter Kühlung mit einer wässerigen Lösung von 10,8 kg m-Phenylendiamin ver setzt. Man stumpft die freie Mineralsäure zum Beispiel mit Natriumacetat ab und gibt dann eine überschüssige Soda enthaltende Lösung von 15,2 kg 3.5-Diamino-benzoesäure hinzu. Der erhaltene Farbstoff wird filtriert und getrocknet.
Additional patent to main patent no. 150006. Process for the production of a black azo dye. The present patent relates to a process for the production of a black azo dye, characterized in that p-nitroaniline is dianotized and coupled with 1-amino-8-naphthol-4,6-disulfonic acid in acidic solution, the monoazo dye in alkaline solution with dianotized 5-nitro-2-amino-l-anisole couples, reduces the disazo dye,
tetrazotized and coupled with 1 mol of m-phenylenediamine and 1 mol of 3,5-diaminobenzoic acid.
The dye obtained in this way is a black, water-soluble powder and dyes cotton in black tones, which are washed and lightfast after treatment with formaldehyde and copper salts.
<I> Example: </I> 13.8 kg of p-nitroaniline are dianotized in the usual way and coupled with 31.9 kg of 1-amirro-8-naphthol-4,6-disulfoic acid in an acidic medium. The monoazo dye obtained is further coupled in a soda-alkaline solution with a diazo solution prepared from 17.2 kg of 5-nitro-2-amino-1-anisole and the isolated disazo is reduced with a solution of 72 kg of crystallized sodium sulphide.
The deposited dye is made into a paste with water and, while cooling, an aqueous solution of 14 kg of sodium nitrite and excess hydrochloric acid are added. The tetrazo suspension obtained in this way is ver sets with cooling with an aqueous solution of 10.8 kg of m-phenylenediamine. The free mineral acid is blunted, for example with sodium acetate, and then a solution of 15.2 kg of 3,5-diamino-benzoic acid containing excess soda is added. The dye obtained is filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH150006T | 1930-10-06 | ||
| CH165038T | 1933-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH165038A true CH165038A (en) | 1933-10-31 |
Family
ID=25715554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH165038D CH165038A (en) | 1930-10-06 | 1933-03-03 | Process for the preparation of a black azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH165038A (en) |
-
1933
- 1933-03-03 CH CH165038D patent/CH165038A/en unknown
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