CH303899A - Process for the preparation of a copper-containing tetrakisazo dye. - Google Patents
Process for the preparation of a copper-containing tetrakisazo dye.Info
- Publication number
- CH303899A CH303899A CH303899DA CH303899A CH 303899 A CH303899 A CH 303899A CH 303899D A CH303899D A CH 303899DA CH 303899 A CH303899 A CH 303899A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- copper
- parts
- dye
- compound
- Prior art date
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 7
- 229910052802 copper Inorganic materials 0.000 title claims description 7
- 239000010949 copper Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- -1 aminomonoazo Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 240000007817 Olea europaea Species 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 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
- 239000000975 dye Substances 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 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
- 239000000203 mixture Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- DBNPDRYVYQWGFW-UHFFFAOYSA-N N.[Cu]=O Chemical compound N.[Cu]=O DBNPDRYVYQWGFW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines kupferhaltigen Tetrakisazofarbstoffes. Das vorliegende Patent. betrifft. ein Ver fahren zur Herstellung eines kupferhaltigen Tetrakisazofarbstoffes, welehes darin besteht, (lass man 1 Mol der Diazoverbindung aus 2- Aininobenzol-l-earbonsäure mit 1 Mol 4-Aceto- aeetylamino-4' - aminodiphenyl - 3' - sulfonsäure vereinigt,
die Aminomonoazoverbindung di- azotiert, den Diazomonoazokörper mit 1 'Hol 1:Amino-2-methoxynaphthalin-6-sulfonsäure kuppelt, die entstandene Aminodisazoverbin- dung weiterdiazotiert, den Diazodisazokörper mit 1:
hlol 1,6-Dioxynaphthalin-5-(2'-carboxy)- benzolazo-3,4'-disulfonsäure kuppelt und den g<B>0'</B> ebildeten Tetrakisazofarbstoff durch Behan deln mit. einem kupferabgebenden Mittel in seine Kupferkomplexverbindung überführt.
Die hier beschriebene 1,6-Dioxy7naphthalin- 5 - C- carboxy) - benzolazo-3,4'-disulfonsäure kann durch Kuppeln von diazotierter 1-Amino- 2-e@ii-boxybenzol-4-sulfonsäure mit.
1-Oxy-6- aniinonaphtlialin-3-sulfonsäure in saurem Me- dium, Diazotieren der erhaltenen Aminomono- azoverbindung und Verkochen der Diazover- bindung hergestellt werden.
Im nachfolgenden Beispiel bedeuten die Teile Gewiehtsteile. Beispiel: 1.3,7 Teile 2-Aminobenzol-1.-earbonsäure werden. in 150 Teilen Wasser diazotiert. Man vereinigt die Diazostispension mit der natrium- bicarbonatalkalisehen Lösung von 48,4 Teilen -1 -- Acetoa eetv lamino - 4' - aminodiphenyl - 3'-sul- fonsäure in 500 Teilen Wasser.
Die entstan- dene Aminomonoazoverbindung wird abge schieden und in 500 Teilen Wasser angerührt. Man trägt die Suspension nach Zugabe von 7 Teilen Natriumnitr it. in eine Mischung aus 30 Teilen konzentrierter Salzsäure und 210 Teilen Eis ein. Nach -vierstündigem Rühren bei 10 ist die Diazotierung beendigt.
Man giesst die Diazosttspension bei 10 zu einer Lö sung aus 27,5 Teilen des Natriumsalzes der 1. Amino-2-methoxynaphthalin - 6 - sulfonsäure, 25 Teilen Natriumcarbonat und 400 Teilen Wasser. Nach Beendigung der Kupplung wird die Aminodisazoverbindung isoliert und in 600 Teilen Wasser angerührt.
Nach Zugabe von 7 Teilen Natriumnitrit trägt man die Suspension bei 10 in 30 Teile konzentrierte S S alzsäure und 200 Teile Eis ein. Die gebildete Diazodisazoverbindung wird abfiltriert und in Form einer Paste bei 10 in eine Lösung aus 51,2 Teilen des Natriumsalzes der 1.,6-Dioxy naphthalin-5-(2'-carboxy)-benzolazo-3,
4'-disul- fonsäure, 300 Teilen Wasser und 300 Teilen Pyridinbasengemisch eingetragen. Der ent standene Tetrakisazofarbstoff wird abgeschie den und abfiltriert.
Zur Überführung in seine Kupferkomplex verbindung wird er in 2500 Teilen Wasser gelöst. Nach Zugabe von 15 Teilen Natrium- , earbonat lässt man der Farbstofflösung bei 85 bis 95 innerhalb von 20 Minuten die durch Versetzen einer Lösung von 75 Teilen kristalli siertem Kupfersulfat in 500 Teilen Wasser mit. 150 Teilen einer wässerigen Ammoniak-, lösung 25% hergestellte Kupferoxydammo- niaklösung zufliessen.
Man kocht die Masse während S Stunden am Rückfluss, salzt dar aus den kupferhaltigen Tetrakisazofarbstoff mittels Zusatz von Salz aus, filtriert ihn ab und troeknet ihn.
Der neue Farbstoff ist ein dunkles Pulver, das sich in Wasser mit grüner und in konzen trierter Schwefelsäure mit graugrüner Farbe löst und Fasern aus Cellulose in oliven Tönen von guter Wasch- und Lichtechtheit, färbt.
Process for the preparation of a copper-containing tetrakisazo dye. The present patent. concerns. a process for the production of a copper-containing tetrakisazo dye, which consists in (let 1 mol of the diazo compound from 2-amino-benzene-1-carboxylic acid be combined with 1 mol of 4-aceto-aeetylamino-4 '- aminodiphenyl - 3' - sulfonic acid,
the aminomonoazo compound diazotized, the diazomonoazo body coupled with 1 'Hol 1: amino-2-methoxynaphthalene-6-sulfonic acid, the aminodisazo compound formed further diazotized, the diazodisazo body with 1:
hlol 1,6-dioxynaphthalene-5- (2'-carboxy) - benzolazo-3,4'-disulfonic acid couples and the tetrakisazo dye formed by treatment with it. converted into its copper complex compound by a copper releasing agent.
The 1,6-dioxy7naphthalene-5-C-carboxy) -benzenazo-3,4'-disulfonic acid described here can be obtained by coupling diazotized 1-amino-2-e @ ii-boxybenzene-4-sulfonic acid with.
1-oxy-6-aniinonaphthalen-3-sulfonic acid can be prepared in an acidic medium, diazotizing the amino monoazo compound obtained and boiling off the diazo compound.
In the following example the parts mean weight parts. Example: 1.3.7 parts of 2-aminobenzene-1-carbonic acid are used. diazotized in 150 parts of water. The diazo suspension is combined with the sodium bicarbonate alkali solution of 48.4 parts of -1-acetoa eetv lamino-4'-aminodiphenyl-3'-sulphonic acid in 500 parts of water.
The aminomonoazo compound formed is separated out and stirred in 500 parts of water. The suspension is worn after the addition of 7 parts of sodium nitrate. into a mixture of 30 parts of concentrated hydrochloric acid and 210 parts of ice. After stirring for four hours at 10, the diazotization is complete.
The Diazosttspension is poured at 10 to a solution of 27.5 parts of the sodium salt of the 1st amino-2-methoxynaphthalene-6-sulfonic acid, 25 parts of sodium carbonate and 400 parts of water. After the coupling has ended, the aminodisazo compound is isolated and stirred up in 600 parts of water.
After adding 7 parts of sodium nitrite, the suspension is introduced at 10 in 30 parts of concentrated hydrochloric acid and 200 parts of ice. The diazodisazo compound formed is filtered off and in the form of a paste at 10 in a solution of 51.2 parts of the sodium salt of 1st, 6-Dioxy naphthalene-5- (2'-carboxy) -benzolazo-3,
4'-disulphonic acid, 300 parts of water and 300 parts of pyridine base mixture entered. The resulting tetrakisazo dye is deposited and filtered off.
To convert it into its copper complex compound, it is dissolved in 2500 parts of water. After adding 15 parts of sodium, carbonate, the dye solution is left at 85 to 95 within 20 minutes with the copper sulfate crystallized by adding a solution of 75 parts in 500 parts of water. 150 parts of an aqueous ammonia solution, 25% produced copper oxide ammonia solution are poured in.
The mass is refluxed for 5 hours, salted out of the copper-containing tetrakisazo dye by the addition of salt, filtered off and dried.
The new dye is a dark powder that dissolves in water with green and in concentrated sulfuric acid with a gray-green color and colors fibers made of cellulose in olive tones with good wash and lightfastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH303899T | 1951-12-18 | ||
| CH301444T | 1952-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH303899A true CH303899A (en) | 1954-12-15 |
Family
ID=25734382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH303899D CH303899A (en) | 1951-12-18 | 1951-12-18 | Process for the preparation of a copper-containing tetrakisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH303899A (en) |
-
1951
- 1951-12-18 CH CH303899D patent/CH303899A/en unknown
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