CH310828A - Process for the production of a metallizable polyazo dye. - Google Patents
Process for the production of a metallizable polyazo dye.Info
- Publication number
- CH310828A CH310828A CH310828DA CH310828A CH 310828 A CH310828 A CH 310828A CH 310828D A CH310828D A CH 310828DA CH 310828 A CH310828 A CH 310828A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- parts
- diazotized
- acid
- dye
- Prior art date
Links
- -1 polyazo Polymers 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000001879 copper Chemical class 0.000 claims description 4
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 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 2
- 239000000975 dye Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- LHTUXJXQOHCGTA-UHFFFAOYSA-N 2-(1-aminonaphthalen-2-yl)-2-hydroxyacetic acid Chemical compound NC1=C(C=CC2=CC=CC=C12)C(C(=O)O)O LHTUXJXQOHCGTA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 1
- 241000784732 Lycaena phlaeas Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide 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
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
-
- 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
- C09B31/16—Trisazo dyes
- C09B31/22—Trisazo dyes from a coupling component "D" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines metallisierbaren Polyazofarbstoffes. Es wurde gefunden, dass man wertvolle, metallisierbare Tris- und Polyazofarbstoffe der allgemeinen Formel
EMI0001.0008
worin Acyl einen Carbacylrest bedeutet, er hält, wenn man n Moleküle einer Diazonium- verbindung der Benzolreihe- (A), die in o- ,
Stellung zur Diazogruppe einen metallisier- baren Substituenten enthält, mit einer mono primären Aminoverbindung der Formel (Acy@l-CH2-CO-NH),i B-NH2 welche Verbindung sich von einer mehrkerni gen, substantiven Polyaminverbindung (B) der Benzolreihe ableitet, und in welcher alle Aminogruppen bis auf eine acyloaeetyliert sind, vereinigt,
den erhaltenen Aminoazofarb- stoff diazotiert und die Diazoverbindung in saurem Mittel mit einer in p-Stellung zur Aminogruppe kuppelnden 1-Amino-2-alkoxy- naphthalinverbindung (D), die substituierte Alkylreste in den Alkoxygruppen und Sulfon- säuregruppen enthalten kann,
vereinigt und den so erhaltenen Aminopolyazofarbst.off di- azotiert und in alkalischem Mittel mit einer 2-Acylamino-6-oxy-naphthalin-8-sulfonsäure kuppelt.
Die neuen Polyazofarbstoffe sind in Form ihrer Alkalisalze in heissem Wasser mit grüner Farbe löslich und färben Cellulosefasern aus dem Glaubersalz enthaltenden Färbebad direkt in oliven, gelbgrünen bis grünen Tönen. Bei der Nachbehandlung der Cehulosefärbungen mit kupferabgebenden Mitteln wird der Farb ton nur wenig verändert, dagegen werden die NTassechtheiten und die Lichtechtheit wesent lich verbessert.
Die Kupferung kann im Färbe bad oder auf frischem Bad mit übliehen Kupfersalzen, wie zum Beispiel Kupferacetat oder Kupfersulfat, in neutralem bis schwach saurem Mittel erfolgen. Gegebenenfalls kann man auch gegen Alkalien beständige Kupfer verbindungen verwenden, wie sie bei der Um setzung von Kupfersulfat mit Natriumtartrat in soloalkalischem Bad erhalten werden.
Gegenstand vorliegenden Patentes ist nun ein Verfahren zur Herstellung eines metalli- sierbaren Trisazofarbstoffes. Das Verfahren ist dadurch gekennzeichnet, d'ass man diazo- tiertes 2-Amino-l-oxy-benzol-4-methylsulfon mit 5-(3'-Acetoa.cetylamino-benzoylamino)-2- amino-benzol-l-sulfonsäure kuppelt, den erhal tenen Monoazofarbstoff weiterdiazotiert,
mit 1-Amino-naphthalin-2-glykolsäure vereinigt, die entstandene Verbindung diazotiert und. mit 2-Benzoy'lamino-6-oxy-naphthalin-8-sulfon- säure kuppelt.
Der erhaltene neue Trisazofarbstoff stellt ein dunkles Pulver dar, das Celllulosefasern in lebhaften, gelbstichig grünen Tönen färbt, die durch Nachbehandlung mit Kupfersalzen licht-, wasch- und säureeeht werden.
<I>Beispiel:</I> 18,7 Teile 2-Amino-1-oxy-benzol-4-methyl- sulfon werden in 200 Teilen Wasser mit 15 Teilen konz. Salzsäure gelöst und bei 10 mit 6,9 Teilen Natriumnitrit diazotiert. Die ent standene Suspension fliesst zu einer Lösung von 41 Teilen 5-(3'-Acetoacetylamino-benzoyl- amino)
-2-amino-ben7ol-1-sulfonsäure in 400 Teilen Wasser und 24 Teilen Natriumbicar- bonat. Nach beendeter Kupplung wird der gelbe 1VZonoazofarbstoff ausgesalzen und ab filtriert.
Den Presskuchen löst man in 1000 Teilen Wasser und versetzt mit 6,9 Teilen Natriumnitrit. Durch Auftropfen auf 40 Teile konz. Salzsäure bei 10-15 erhält man eine gelbe Diazosuspension, die nach vierstündigem Rühren mit 5 Teilen Natriumcarbonat. schwach kongosauer gestellt und mit einer Lösung von 21,7 Teilen 1-Amino-naphthalin-2-glykolsäure und 20 Teilen Natriumaeetat. vereinigt wird. Zur Beschleunigung der Kupplung wird mit 4 Teilen Natriumcarbonat bis zur schwach sauren Reaktion abgestumpft.
Man löst den gebildeten Disazofarbstoff mit. 5 Teilen Ätz natron, vermischt mit 400 Teilen Kochsalz, 60 Teilen konz. Salzsäure und diazotiert mit 8,2 Teilen Natriumnitrit bei 20 . Nach be endeter Diazotierung wird filtriert und ge waschen. Die Diazoverbindung wird in Gegen wart von 150 Teilen Pyridin und 20 Teilen Natriumcarbonat mit 34,3 Teilen 2-Benzoyl- amino-6-oxy-naphthalin-8-sulfonsäure in 200 Teilen Wasser vereinigt.
Der grüne Trisazofarbstoff der Formel
EMI0002.0041
wird mit wenig Kochsalz ausgeschieden, ab filtriert. und von anhaftenden Verunreinigun gen freigewaschen. Er stellt ein dunkles Pul ver dar, welches sich in Wasser mit grüner und in konz. Schwefelsäure mit olivgrüner Farbe löst. Er färbt Fasern aus natürlicher oder regenerierter Cellulose in lebhaften, gelb stichig grünen Tönen an. Durch Nachbehand- hing mit Kupfersalzen werden die Färbungen licht-, wasch- und säureecht.
Process for the production of a metallizable polyazo dye. It has been found that valuable, metallizable tris and polyazo dyes of the general formula
EMI0001.0008
where acyl means a carbacyl radical, it holds when one n molecules of a diazonium compound of the benzene series- (A), which in o-,
Position to the diazo group contains a metallizable substituent, with a mono primary amino compound of the formula (Acy @ l-CH2-CO-NH), i B-NH2 which compound is derived from a polynuclear, substantive polyamine compound (B) of the benzene series, and in which all amino groups except for one are acyloaeetylated, combined,
the aminoazo dye obtained is diazotized and the diazo compound is diazotized in an acidic agent with a 1-amino-2-alkoxynaphthalene compound (D) which couples in the p-position to the amino group and which may contain substituted alkyl radicals in the alkoxy groups and sulfonic acid groups,
combined and the resulting Aminopolyazofarbst.off diazotized and coupled in an alkaline medium with a 2-acylamino-6-oxy-naphthalene-8-sulfonic acid.
The new polyazo dyes, in the form of their alkali salts, are soluble in hot water with a green color and dye cellulose fibers from the dyebath containing Glauber's salt directly in olive, yellow-green to green shades. In the aftertreatment of the cehulose dyeings with copper-releasing agents, the color tone is only slightly changed, but the NTassfastness and lightfastness are significantly improved.
The copper plating can be done in the dye bath or on a fresh bath with common copper salts, such as copper acetate or copper sulfate, in a neutral to slightly acidic agent. If necessary, you can also use copper compounds resistant to alkalis, such as those obtained when converting copper sulfate with sodium tartrate in a solo alkaline bath.
The present patent now relates to a process for the production of a metallizable trisazo dye. The process is characterized in that diazotized 2-amino-1-oxy-benzene-4-methylsulfone is coupled with 5- (3'-acetoa.cetylamino-benzoylamino) -2-aminobenzene-1-sulfonic acid , further diazotizes the monoazo dye obtained,
combined with 1-amino-naphthalene-2-glycolic acid, the resulting compound is diazotized and. with 2-Benzoy'lamino-6-oxy-naphthalene-8-sulfonic acid.
The new trisazo dye obtained is a dark powder that dyes cellulose fibers in lively, yellowish green tones, which are light, washable and acidic after treatment with copper salts.
<I> Example: </I> 18.7 parts of 2-amino-1-oxy-benzene-4-methylsulfone are concentrated in 200 parts of water with 15 parts. Dissolved hydrochloric acid and diazotized at 10 with 6.9 parts of sodium nitrite. The resulting suspension flows into a solution of 41 parts of 5- (3'-acetoacetylamino-benzoyl-amino)
-2-amino-ben7ol-1-sulfonic acid in 400 parts of water and 24 parts of sodium bicarbonate. When the coupling is complete, the yellow 1V zonoazo dye is salted out and filtered off.
The press cake is dissolved in 1000 parts of water and 6.9 parts of sodium nitrite are added. By dripping onto 40 parts of conc. Hydrochloric acid at 10-15 gives a yellow diazo suspension which, after stirring for four hours with 5 parts of sodium carbonate. Made weakly Congo acid and with a solution of 21.7 parts of 1-amino-naphthalene-2-glycolic acid and 20 parts of sodium acetate. is united. To accelerate the coupling, 4 parts of sodium carbonate are used to truncate until the reaction is weakly acidic.
The disazo dye formed is also dissolved. 5 parts of caustic soda, mixed with 400 parts of table salt, 60 parts of conc. Hydrochloric acid and diazotized with 8.2 parts of sodium nitrite at 20. When the diazotization has ended, it is filtered and washed. The diazo compound is combined in the presence of 150 parts of pyridine and 20 parts of sodium carbonate with 34.3 parts of 2-benzoylamino-6-oxynaphthalene-8-sulfonic acid in 200 parts of water.
The green trisazo dye of the formula
EMI0002.0041
is excreted with a little salt, filtered off. and washed free of adhering impurities. It represents a dark powder, which is green in water and in conc. Dissolves sulfuric acid with an olive green color. It stains fibers made from natural or regenerated cellulose in lively, yellow, green tones. Post-treatment with copper salts makes the colorations light, washable and acid-fast.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH310828T | 1952-10-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH310828A true CH310828A (en) | 1955-11-15 |
Family
ID=4494306
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH310828D CH310828A (en) | 1952-10-16 | 1952-10-16 | Process for the production of a metallizable polyazo dye. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH310828A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4211698A (en) * | 1977-08-23 | 1980-07-08 | Ciba-Geigy Corporation | Disazo dyes containing an acetoacetanilide middle component |
-
1952
- 1952-10-16 CH CH310828D patent/CH310828A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4211698A (en) * | 1977-08-23 | 1980-07-08 | Ciba-Geigy Corporation | Disazo dyes containing an acetoacetanilide middle component |
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