CH192978A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH192978A CH192978A CH192978DA CH192978A CH 192978 A CH192978 A CH 192978A CH 192978D A CH192978D A CH 192978DA CH 192978 A CH192978 A CH 192978A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- azo dye
- parts
- production
- green
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid 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
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000725 suspension Substances 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/30—Other polyazo dyes
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 187120. Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Azofarbstoff erhält, wenn man 1 Mol 4',4"- Diaminodibenzoyl -1;
3@- @diamino - 8 - ogynaph- thaIin-6-sulfonsäure mit 1 Mol des diazotier- ten Azofarbstoffes aus 2,5-Dichloranilin-4- sulfonsäure und 2-Methogy-l-aminonaphtha- lin-7-sulfonsäure vereinigt.
Der so erhaltene Farbstoff bildet ein dunkles Pulver, ,das sich in Wasser mit .omünlichblauer Farbe löst und Baumwolle in grünlich-blauen Tönen färbt, die durch Weiterdiazotieren auf der Faser und Entwickeln mit 1-Phenyl-3-methyl-,5- pyrazolon grün, licht- und waschecht werden. <I>Beispiel:</I> 24,2 Teile der 2.,5-Dichloranilin-4-sulfon- säure werden in 600 Teilen Wasser und 6 Teilen Natriumkarbonat gelöst und auf 0 abgekühlt.
Hierauf gibt man 25 Teile einer 30%igen Salzsäure zu und lässt unter gutem Rühren 35 Teile einer 20%igen Natrium- nitritlösung unter die Flüssigkeitsoberfläche einlaufen. Nach beendigter Diazotierung ,gibt man 25 Teile 2-Methogy-l-aminonaph- thalin-7-sulfonsäure, in 600 Teilen Wasser und 6 Teilen Natriumkarbonat neutral gelöst, hinzu.
Die Kupplung geht unter Zusatz von Natriumacetat sehr gut und man lässt über Nacht rühren. Durch Zusatz einer 4 % igen Natriumhydrogydlösung wird der gebildete Monoazofarbstoff neutral in Lösung ge bracht, 35 Teile einer 20%igen Natrium- nitritlösung eingetragen und bei 0 bis 5 indirekt diazotiert,
indem man 30 Teile einer 30%igen .Salzsäure unter gutem Rühren auf einmal einstürzt. Dann lässt man noch 4 :Stunden bei 10 bis<B>15'</B> rühren, .scheidet aus der Lösung durch gochsalzzusatz die Diazoverbindung ab und schwemmt sie in 1000 Teilen Eiswasser an.
Diese Auf- schwemmung lässt man in eine Lösung von 50 Teilen 4',4" - Diaminodibenzoyl - 1,3 - ,di- amino-8-ogynaphthalin-:6-sulfonsäure in 400 Teilen Wasser unter Zusatz von 30 Teilen Ammoniak (25%ig) und 10-0 Teilen Pyridin zulaufen und rührt über Nacht. Der gebil- dete Disazofarbstoff wird ausgesalzen, ab: filtriert und getrocknet.
Additional patent to main patent No. 187120. Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1 mol of 4 ', 4 "-diaminodibenzoyl -1;
3 @ - @diamino - 8 - ogynaphthaIin-6-sulfonic acid combined with 1 mol of the diazotized azo dye from 2,5-dichloroaniline-4-sulfonic acid and 2-methogy-1-aminonaphthalin-7-sulfonic acid.
The dye thus obtained forms a dark powder, which dissolves in water with a .omünlichblauer color and dyes cotton in greenish-blue tones, which by further diazotizing on the fiber and developing with 1-phenyl-3-methyl-, 5-pyrazolone green , lightfast and washfast. <I> Example: </I> 24.2 parts of the 2nd, 5-dichloroaniline-4-sulfonic acid are dissolved in 600 parts of water and 6 parts of sodium carbonate and cooled to zero.
25 parts of a 30% strength hydrochloric acid are then added and 35 parts of a 20% strength sodium nitrite solution are allowed to run under the surface of the liquid with thorough stirring. When the diazotization is complete, 25 parts of 2-methogy-1-aminonaphthalene-7-sulfonic acid, dissolved neutral in 600 parts of water and 6 parts of sodium carbonate, are added.
The coupling goes very well with the addition of sodium acetate and the mixture is left to stir overnight. By adding a 4% sodium hydrogen solution, the monoazo dye formed is brought into neutral solution, 35 parts of a 20% sodium nitrite solution are added and diazotized indirectly at 0 to 5,
by collapsing 30 parts of a 30% strength hydrochloric acid at once with thorough stirring. The mixture is then left to stir for a further 4 hours at 10 to 15 ', the diazo compound is separated out from the solution by adding sodium chloride and washed over with 1000 parts of ice water.
This suspension is left in a solution of 50 parts of 4 ', 4 "-diaminodibenzoyl-1,3-, di-amino-8-ogynaphthalene-: 6-sulfonic acid in 400 parts of water with the addition of 30 parts of ammonia (25% ig) and 10-0 parts of pyridine run in and stir overnight. The disazo dye formed is salted out, filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH187120T | 1934-09-29 | ||
| CH192978T | 1934-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH192978A true CH192978A (en) | 1937-09-15 |
Family
ID=25721480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH192978D CH192978A (en) | 1934-09-29 | 1934-09-29 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH192978A (en) |
-
1934
- 1934-09-29 CH CH192978D patent/CH192978A/en unknown
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