CH248689A - Process for the production of a metallizable polyazo dye. - Google Patents
Process for the production of a metallizable polyazo dye.Info
- Publication number
- CH248689A CH248689A CH248689DA CH248689A CH 248689 A CH248689 A CH 248689A CH 248689D A CH248689D A CH 248689DA CH 248689 A CH248689 A CH 248689A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- dye
- acid
- oxy
- metallizable
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- -1 polyazo Polymers 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 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
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 243333. Verfahren zur Herstellung eines metallisierbaren Polyazofarbstoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines metallisier baren Polyazofarbstoffes. Das Verfahren ist dadurch gekennzeichnet, dass 1-Amino-8-oxy- na.phthalin-3,
6-disulfonsäure sauer mit diazo- tiertem 1-Amino-4-nitro-benzol und alkalisch mit diazotierter 5-Nitro-2-amino-benzoesäure gekuppelt, der erhaltene Dinitro-disazofarb- stoff zum Diamino - disazofarbstoff redu ziert,
dieser tetra.zotiert und beidseitig mit dem durch saure Kupplung von diazotierter 1-Amino-4-oxy-benzol-3-carbonsäure mit 2- i@.mino-5-oxy-naphtha.lin-7-sulfonsäure erhal tenen Monoazofarbstoff gekuppelt wird.
Der neue Hexakisazofarbstoff bildet ein dunkles Pulver, das sich in Wasser mit rot stichig blauer und in konzentrierter Schwef el- säure mit blaugrauer Farbe löst. Er färbt Fasern aus natürlicher oder regenerierter Cellulose in grauen Tönen.
Beim Nachbehandeln mit Kupfersulfat oder Chromsulfat werden diese in der Nuance kaum verändert, dagegen in den Na.ssecht- heiten wesentlich verbessert. <I>Beispiel:</I> 13,8 Teile 1-Amino-4-nitro-benzol werden in üblicher Weise dianotiert und in mineral saurem Medium mit 31,9 Teilen 1-Amino-8- oxy-naphthalin-3,6-disulfonsäure gekuppelt.
Man macht mit überschüssiger Soda alkalisch und vereinigt den erhaltenen Monoazofa.rb- stoff mit einer aus 18,2 Teilen 5-Nitro-2- amino-benzoesäure, 6,9 Teilen Natriumnitrit und der nötigen Menge Salzsäure hergestell ten Diazoniumlösung. Der fertig gebildete Disazofarbstoff scheidet sich in bronzieren- den Kristallen aus. Er wird abfiltriert, in der notwendigen Menge Wasser gelöst. und bei 35 mit 23,4 Teilen Natriumsulfid reduziert.
Der mit Salzsäure abgeschiedene Diamino- disazofarbstoff wird in Sodalösung gelöst, vom gebildeten Schwefel abfiltriert, mit 13,8 Teilen Natriumnitrit vermischt und in über schüssige verdünnte Salzsäure eingetropft. Nach einigen Stunden ist die Bildung der Tetrazoverbindung beendet.
Man vereinigt sie mit 80,6 Teilen des durch saure Kupplung von dianotierter 1-Amino-4-oxy-benzo1-3-car- bonsKure mit 2 - Amino - 5 - oxy-naphthalin-7- sulfonsäure erhaltenen Monoazofarbstoffes. in Gegenwart von 80 Teilen Soda. Nach einiger Zeit ist die Kupplung beendet und der Hexa- kisazofarbstoff abgeschieden. Er wird ab filtriert, mit verdünnter Sole gewaschen und getrocknet.
Additional patent to main patent No. 243333. Process for the production of a metallizable polyazo dye. The present patent is a process for the preparation of a metallizable polyazo dye. The method is characterized in that 1-amino-8-oxy- na.phthalin-3,
6-disulfonic acid coupled acidically with diazotized 1-amino-4-nitro-benzene and alkaline with diazotized 5-nitro-2-amino-benzoic acid, the resulting dinitro-disazo dye is reduced to the diamino-disazo dye,
this tetra.zotiert and is coupled on both sides with the monoazo dye obtained by acidic coupling of diazotized 1-amino-4-oxy-benzene-3-carboxylic acid with 2- i @ .mino-5-oxy-naphtha.lin-7-sulfonic acid .
The new hexakisazo dye forms a dark powder that dissolves in water with a red, tinged blue color and in concentrated sulfuric acid with a blue-gray color. It dyes fibers made of natural or regenerated cellulose in gray tones.
After treatment with copper sulphate or chromium sulphate, the shade is hardly changed, but the wetness properties are significantly improved. <I> Example: </I> 13.8 parts of 1-amino-4-nitro-benzene are dianotized in the customary manner and mixed with 31.9 parts of 1-amino-8-oxy-naphthalene-3,6 in a mineral acid medium -disulfonic acid coupled.
It is made alkaline with excess soda and the resulting monoazofa.rb material is combined with a diazonium solution prepared from 18.2 parts of 5-nitro-2-aminobenzoic acid, 6.9 parts of sodium nitrite and the necessary amount of hydrochloric acid. The completely formed disazo dye separates out in bronzing crystals. It is filtered off and dissolved in the necessary amount of water. and reduced at 35 with 23.4 parts of sodium sulfide.
The diamino disazo dye deposited with hydrochloric acid is dissolved in soda solution, the sulfur formed is filtered off, mixed with 13.8 parts of sodium nitrite and added dropwise to excess dilute hydrochloric acid. The formation of the tetrazo compound has ended after a few hours.
They are combined with 80.6 parts of the monoazo dye obtained by acidic coupling of dianotized 1-amino-4-oxy-benzo1-3-carboxylic acid with 2-amino-5-oxy-naphthalene-7-sulfonic acid. in the presence of 80 parts of soda. After some time, the coupling has ended and the hexakisazo dye has been deposited. It is filtered off, washed with dilute brine and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH248689T | 1944-05-25 | ||
| CH243333T | 1944-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH248689A true CH248689A (en) | 1947-05-15 |
Family
ID=25728801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH248689D CH248689A (en) | 1944-05-25 | 1944-05-25 | Process for the production of a metallizable polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH248689A (en) |
-
1944
- 1944-05-25 CH CH248689D patent/CH248689A/en unknown
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