CH211001A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211001A CH211001A CH211001DA CH211001A CH 211001 A CH211001 A CH 211001A CH 211001D A CH211001D A CH 211001DA CH 211001 A CH211001 A CH 211001A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- oxy
- azo dye
- parts
- preparation
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 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 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 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
- C09B35/38—Trisazo dyes ot the type
- C09B35/40—Trisazo dyes ot the type the component K being a dihydroxy or polyhydroxy compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 208538. Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass ein neuer Azo- farbstoff hergestellt werden kann, wenn man 1 Mol 1,3-Dioxybenzol einerseits mit 1 Mol der Diazoverbindung aus 1-Oxy-2-aminoben- zol-4-sulfamid und anderseits mit 1 Mol der Diazoazoverbindung, die bei der einseitigen Kupplung tetrazotierten 4,
4'-Diaminodiphenyls mit 3-Methyl-2-oxy-l-benzoesäure entsteht, vereinigt.
Der erhaltene Farbstoff bildet ein dunkel gefärbtes Pulver, das sich in Wasser und verdünnten Alkalien mit bräunlicher und in konzentrierter Schwefelsäure mit rotvioletter Farbe löst. Baumwolle und regenerierte Zel lulose werden aus Glaubersalz enthaltendem Bade in braunen Tönen gefärbt, die durch Nachbehandlung mit Metall-, insbesondere Kupfersalzen; vorzüglich licht- und waschecht werden.
<I>Beispiel:</I> 18,4 Teile 4,4'-Diaminodiphenyl werden in bekannter Weise mit 52 Teilen konzen trierter Salzsäure und 1.4 Teilen Natrium nitrit in die Tetrazoverbindung übergeführt. Diese lässt man zu einer bei 4 C gehaltenen Lösung fliessen, die man aus 18 Teilen 3- Methyl-2-oxy-l-benzoesäure und 55 Teilen wasserfreiem Natriumcarbonat erhalten hat.
In kurzer Zeit bildet sich die braune Diazo- azoverbindung der Formel
EMI0001.0022
Diese kombiniert man nun mit dem Mono- azofarbstoff, den man erhält, wenn man die Diazoverbindung aus 18,8 Teilen 1-Ogy-2- aminobenzol-4-sulfamid in Gegenwart von 25 Teilen wasserfreiem Natriumcarbonat rnit 11 Teilen 1,3-Dioxyberrzol kuppelt.
Die Kupplung zum Morroazofarbstoff ist sofort beendet und die rote Lösung desselben wird nun zu der oben erhaltenen Diazoazoverbindung gegeben, worauf eine braune Fällung des Trisazo- farbstoffes entsteht.
Man rührt nun 10-15 Stunden, erwärmt darauf auf<B>60'</B> und gibt 200 Teile einer 15 %igen Kochsalzlösung zu, nur eine gut filtrierbare Form des Farbstoffes zu erhalten. Man filtriert noch warm, trocknet und pul verisiert den schwärzlichen Filterrückstand.
<B> Additional patent </B> to main patent no. 208538. Process for the production of an azo dye. It has been found that a new azo dye can be prepared if 1 mole of 1,3-dioxybenzene is mixed with 1 mole of the diazo compound from 1-oxy-2-aminobenzene-4-sulfamide and with 1 mole of the diazoazo compound , the tetrazotized 4,
4'-Diaminodiphenyls formed with 3-methyl-2-oxy-1-benzoic acid, combined.
The dye obtained forms a dark-colored powder which dissolves in water and dilute alkalis with a brownish color and in concentrated sulfuric acid with a red-violet color. Cotton and regenerated Zel lulose are dyed from bath containing Glauber's salt in brown tones, which by post-treatment with metal, especially copper salts; excellent lightfast and washfast.
<I> Example: </I> 18.4 parts of 4,4'-diaminodiphenyl are converted into the tetrazo compound in a known manner with 52 parts of concentrated hydrochloric acid and 1.4 parts of sodium nitrite. This is allowed to flow to a solution kept at 4 ° C. which has been obtained from 18 parts of 3-methyl-2-oxy-1-benzoic acid and 55 parts of anhydrous sodium carbonate.
The brown diazo-azo compound of the formula is formed in a short time
EMI0001.0022
This is then combined with the monoazo dye which is obtained when the diazo compound is coupled from 18.8 parts of 1-Ogy-2-aminobenzene-4-sulfamide in the presence of 25 parts of anhydrous sodium carbonate with 11 parts of 1,3-dioxyberrzene .
The coupling to the Morroazo dye is ended immediately and the red solution of the same is now added to the diazoazo compound obtained above, whereupon a brown precipitate of the Trisazo dye results.
The mixture is then stirred for 10-15 hours, then heated to <B> 60 '</B> and 200 parts of a 15% sodium chloride solution are added to obtain only a readily filterable form of the dye. It is filtered while warm, dried and pulverized the blackish filter residue.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208538T | 1938-07-22 | ||
| CH211001T | 1938-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211001A true CH211001A (en) | 1940-08-15 |
Family
ID=25724530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211001D CH211001A (en) | 1938-07-22 | 1938-07-22 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211001A (en) |
-
1938
- 1938-07-22 CH CH211001D patent/CH211001A/en unknown
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