CH205532A - Process for the preparation of a water-soluble azo dye. - Google Patents
Process for the preparation of a water-soluble azo dye.Info
- Publication number
- CH205532A CH205532A CH205532DA CH205532A CH 205532 A CH205532 A CH 205532A CH 205532D A CH205532D A CH 205532DA CH 205532 A CH205532 A CH 205532A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- soluble azo
- azo dye
- preparation
- soluble
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- 239000002966 varnish Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 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
- 150000001412 amines Chemical class 0.000 description 2
- LHFBQVAMBIBANE-UHFFFAOYSA-N benzenesulfonate;dimethylazanium Chemical compound C[NH2+]C.[O-]S(=O)(=O)C1=CC=CC=C1 LHFBQVAMBIBANE-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- CWESERWNUIUBJU-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1Cl CWESERWNUIUBJU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines wasserlöslichen Azofarbstofes. Es wurde gefunden, dass man wertvolle wasserlösliche Azofarbstoffe erhält, wenn man Diazoverbindungen von Aminen der allge meinen Zusammensetzung:
EMI0001.0004
worin g und Y Wasserstoff oder gleiche oder verschiedene aliphatische, aromatische oder aliphatisch-aromatische Reste bedeuten, mit beliebigen Kupplungskomponenten vereinigt.
Mit den so erhaltenen Farbstoffen werden, insbesondere auf Wolle, Färbungen von schi- guter Lichtechtheit erhalten. Weiterhin kön nen einige der neuen Farbstoffe in sehr licht echte Lacke übergeführt werden.
Die bei dem vorliegenden Verfahren als Diazokomponenten angewendeten Amine kön- nen durch Umsetzung der entsprechenden 1- Chlor-2-nitrobenzol-4-sulfamide mit Natrium- stilfit und anschliessende Reduktion der er haltenen Nitroverbindung hergestellt werden.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser löslichen Azofarbstoffes, welches dadurch ge kennzeichnet ist, dass man die Diazoverbin- dungvon 1-Amiiio-3-sulfonsäuredimethylamid- benzol-6-sulfonsäure mit 1-(2'-Chlorphenyl)-3- methyl-5-pyrazolon kuppelt.
<I>Beispiel:</I> Eine aus 280 Gewichtsteilen 1-Amino-3- sulfonsäuredimethylamid-benzol-6-sulfonsäure und der äquivalenten Menge Natriumcarbonat erhaltene wässerige Lösung läuft nach Zugabe der berechneten Menge Natriumnitrit in 250 Volumteile Salzsäure von 200 B6, die mit Eiswasser verdünnt sind, ein.
Die erhaltene Diazosuspension wird mit einer sodaalkali- schen Lösung von 208,5 Gewichtsteilen 1- (2'-Chlorpheny 1) - 3 - nietliyl- "5 - pyrazolon ver einigt. Nach beendeter Kupplung wird der Farbstoff abgesaugt und getrocknet.
Er stellt ein gelbes, in Wasser mit gelber Farbe lösliches Pulver dar. Die daraus her gestellten gelben Drucklacke zeichnen sieh durch sehr gute Lichtechtheit aus.
Process for the preparation of a water-soluble azo dye. It has been found that valuable water-soluble azo dyes are obtained if diazo compounds of amines of the general composition are:
EMI0001.0004
in which g and Y are hydrogen or identical or different aliphatic, aromatic or aliphatic-aromatic radicals, combined with any coupling components.
With the dyes obtained in this way, dyeings of good lightfastness are obtained, especially on wool. In addition, some of the new dyes can be converted into very light-resistant coatings.
The amines used as diazo components in the present process can be prepared by reacting the corresponding 1-chloro-2-nitrobenzene-4-sulfamides with sodium stilfit and then reducing the nitro compound obtained.
The present patent relates to a process for the preparation of a water-soluble azo dye, which is characterized in that the diazo compound of 1-amino-3-sulfonic acid dimethylamide-benzene-6-sulfonic acid with 1- (2'-chlorophenyl) -3 - methyl-5-pyrazolone couples.
<I> Example: </I> An aqueous solution obtained from 280 parts by weight of 1-amino-3-sulfonic acid dimethylamide-benzene-6-sulfonic acid and the equivalent amount of sodium carbonate runs after adding the calculated amount of sodium nitrite in 250 parts by volume of hydrochloric acid of 200 B6, which are diluted with ice water.
The diazo suspension obtained is combined with a soda-alkaline solution of 208.5 parts by weight of 1- (2'-chloropheny 1) -3-nietliyl- "5-pyrazolone. When the coupling is complete, the dye is filtered off with suction and dried.
It is a yellow powder that is soluble in water with a yellow color. The yellow printing varnishes made from it are characterized by very good lightfastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE205532X | 1937-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH205532A true CH205532A (en) | 1939-06-30 |
Family
ID=5787712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205532D CH205532A (en) | 1937-06-22 | 1938-06-13 | Process for the preparation of a water-soluble azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH205532A (en) |
-
1938
- 1938-06-13 CH CH205532D patent/CH205532A/en unknown
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