CH228819A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH228819A CH228819A CH228819DA CH228819A CH 228819 A CH228819 A CH 228819A CH 228819D A CH228819D A CH 228819DA CH 228819 A CH228819 A CH 228819A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- dye
- amino
- preparation
- stilbene
- Prior art date
Links
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims description 4
- 235000021286 stilbenes Nutrition 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 239000000987 azo dye Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- UETHPMGVZHBAFB-OWOJBTEDSA-N 4,4'-dinitro-trans-stilbene-2,2'-disulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O UETHPMGVZHBAFB-OWOJBTEDSA-N 0.000 claims description 2
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000203 mixture Substances 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
- 206010073261 Ovarian theca cell tumour Diseases 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-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
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 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
- 230000003472 neutralizing effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/04—Stilbene-azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 217234. Verfahren zur Darstellung eines Stilbenfarbstoffes. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines Stilbenfarbstoffes,dadurch .gekennzeichnet, dass man 4,4'-Dinitrostilben-2,2'-disulfonsäure mit einem Gemisch aus dem verseiften Azo,
- farbstoff m-Aminobenzoesiäure --> o-Meth- oxyphenylam;inom:ethylsuI,fo#ns,äure und dem Azofarbstoff 4-Chlor-2-amino-l-oxybenzol 3'-Amino-C-phenyl-1,2-N-thiazoI.o,-5- ogynaphthalin-7-suHonsäure kondensiert und das Kondensationsprodukt anschliessend mit kupferabgebenden Mitteln behandelt.
<I>Beispiel:</I> 27,1 Teile des verseiften Azofarbstoffes aus m-Aminobenzoesäune und o-Me@th:o@gy- phenylaminom-ethylsu-Ifon;
säure und 52,7 Teile .des Farbstoffes, hergestellt durch Kuppeln von diazotiertem 4-Chlor-2-amino-l-.ogybenzol mit 3'-Amino-C-phenyl-1,2-N-thiazolo-5-ogy- riaphthalin-7-,sulfonsäure in soloalkalischer Lösung in Gegenwart von Pyridin, werden mit 47,4 Teilen 4,4'-,dinitro,stilben-2,
2'-.disulfon- saurem Natrium in 600 Teilen Wasser und 80 Teilen Natronlauge 36 B6 in üblicher Weise 10 Stunden kondensiert, nachdem Er kalten neutralisiert, mit Kochsalz ausgefällt und filtriert.
Anschliessend wird der Farbstoff in üblicher Weise mit kupferabgebenden Mit teln in die Kupferverbindung übergeführt.
Er stellt .getrocknet ein dunkelviolettes Pulver dar, das sich in Wasser mit brauner, in kon- zentrierter Schwefelsäure mit marineblauer Farbe löst und Cellulosefasern in braunen Tönen von guter Licht-, Alkali- und Säure echtheit färbt.
Additional patent to main patent No. 217234. Process for the preparation of a stilbene dye. The subject of the present additional patent is a process for the preparation of a stilbene dye, characterized in that 4,4'-dinitrostilbene-2,2'-disulfonic acid is mixed with a mixture of the saponified azo,
- dye m-aminobenzoic acid -> o-methoxyphenylam; inom: ethylsuI, fo # ns, acid and the azo dye 4-chloro-2-amino-1-oxybenzene 3'-amino-C-phenyl-1,2- N-thiazoI.o, -5- ogynaphthalene-7-suHonic acid condensed and the condensation product then treated with copper-releasing agents.
<I> Example: </I> 27.1 parts of the saponified azo dye from m-aminobenzoic acid and o-Me @ th: o @ gy-phenylaminom-ethylsu-Ifon;
acid and 52.7 parts of the dye, prepared by coupling diazotized 4-chloro-2-amino-1-.ogybenzene with 3'-amino-C-phenyl-1,2-N-thiazolo-5-ogyriaphthalene -7-, sulfonic acid in solo alkaline solution in the presence of pyridine, with 47.4 parts of 4,4 '-, dinitro, stilbene-2,
2 '-. Disulphonic acid sodium in 600 parts of water and 80 parts of sodium hydroxide solution 36 B6 condensed in the usual way for 10 hours, after neutralizing cold, precipitated with sodium chloride and filtered.
The dye is then converted into the copper compound in the usual way with copper-releasing means.
When dried, it is a dark violet powder that dissolves in water with a brown color, and in concentrated sulfuric acid with a navy blue color and dyes cellulose fibers in brown shades of good light, alkali and acid fastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228819T | 1939-07-03 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH228819A true CH228819A (en) | 1943-09-15 |
Family
ID=25725947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228819D CH228819A (en) | 1939-07-03 | 1939-07-03 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH228819A (en) |
-
1939
- 1939-07-03 CH CH228819D patent/CH228819A/en unknown
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