CH298035A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH298035A CH298035A CH298035DA CH298035A CH 298035 A CH298035 A CH 298035A CH 298035D A CH298035D A CH 298035DA CH 298035 A CH298035 A CH 298035A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- dye
- aminophenyl
- methylbenzthiazole
- azo dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 8
- -1 nitroazo Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 244000061775 Olea africana Species 0.000 claims description 2
- 235000002852 Olea africana Nutrition 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007747 plating 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
- CIQWSXLSSTYHKB-UHFFFAOYSA-N 2-(4-aminophenyl)-6-methyl-3h-1,3-benzothiazole-2-sulfonic acid Chemical compound S1C2=CC(C)=CC=C2NC1(S(O)(=O)=O)C1=CC=C(N)C=C1 CIQWSXLSSTYHKB-UHFFFAOYSA-N 0.000 claims 1
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007865 diluting Methods 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
- 239000000203 mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 29.5052. verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man zu. einem wertvollen Azofarbstoff gelangt, wenn man diazotierte 5-Nitro-2-amino-benzoesäure in al kalischem Medium mit der 2-[4'-(8"-Oxynaph- thyl - [9-"'] -aminophenyl) ] -6-methylbenzthiazol- X,6"-disulfonsäure,
in welcher die in X Stellung befindliche Sulfonsäuregruppe die selbe Stellung einnimmt wie die Sulfonsäure- gruppe der durch Sulfonieren von 2-(4'- Aminophenyl) -,6 - methylbenzt.hiazol mittels konzentrierter Schwefelsäure erhältlichen 2 (4'- Aminophenyl) @6-methylbenzthiazolsulfon- säure, kuppelt,
den so erhaltenen Nitroazo- farbstoff zum Aminoazofarbstoff reduziert und diesen zusammen mit 4-Amino-2-chlor-4'- oxy-1,1'-azobenzol-3'-carbonsäure phosgeniert.
Der neue Farbstoff bildet ein dunkles Pul ver, das sieh in Wasser mit oliver Farbe löst und Baumwolle nach dem ein- oder zwei- badigen Nachkupferungsverfahren in brau nen Olivetönen von guter Wasch- und Licht echtheit färbt.
Beispiel: 18,2 Teile 5-Nitro-2-aminabenzoesäure wer den in bekannter Weise diazotiert. Ander seits werden 55 Teile 2-[4'-(S"-Oxynaphthyl- [ 2" ] - aminophenyl) ] - 6 - methylbenzthiazol- X,
6"-disulfonsäure in 200 Teilen Wasser un ter Zusatz von 50 Teilen 30prozentiger wü.s- seriger Ammoniaklösung gelöst und bei 0 die diazotierte 5-Nitro-2-aminobenzoesäure zu dieser Lösung unter Rühren zugegeben.
Wenn die Monoazo-Kupplung nach mehr stündigem Rühren beendet ist, erwärmt man das Kupplungsgemisch ohne zu verdünnen auf 50 und gibt unter Rühren eine konzentrierte wässerige Lösung von 42 'Teilen kristallisier tem Schwefelnatrium zu. Durch die Reak tion steigt die Temperatur auf 58 . Man er wärmt noch 1 Stunde auf 75 , dann säuert man vorsichtig mit Salzsäure an und filtriert.
Der gebildete Aminoazofarbstoff wird durch Umlösen aus schwach alkalischer, verdünnter, wässeriger Lösung von Schwefelrückständen befreit und mit Natriumchlorid abgeschieden, abfiltriert und getrocknet.
14,1 Teile des so gewonnenen Aminoazo- fa.rbstoffes werden zusammen mit 6,3 Teilen des Natriumsalzes des 4-Amino-2-chlor-4'- oxy-1,1'-azubenzol 3'-carbonsäure in 2000 Tei len Wasser gelöst, der Lösung 20 Teile Na- triumearbonat zugesetzt und bei 30 bis 35 unter Rühren, Phosgen eingeleitet.
Man be handelt - unter Ersatz des verbrauchten Natriumcarbonats - so lange mit Phosgen, bis keine freie Aminogruppe mehr nachweisbar ist. Der gebildete unsymmetrische Harnstoff wird abfiltriert, aus wässeriger, natrium- carbonat-alkalischer Lösung umgelöst und mit Hilfe von Natriumehlorid als Natriumsalz ab geschieden.
<B> Additional patent </B> to main patent No. 29.5052. process for the production of an azo dye. It was found that one too. a valuable azo dye is obtained when diazotized 5-nitro-2-amino-benzoic acid is mixed with 2- [4 '- (8 "-oxynaphthyl - [9-"'] -aminophenyl)] -6- in alkaline medium methylbenzthiazole-X, 6 "-disulfonic acid,
in which the sulfonic acid group in the X position occupies the same position as the sulfonic acid group of the 2 (4'-aminophenyl) @ 6- obtainable by sulfonating 2- (4'-aminophenyl) -, 6 - methylbenzt.hiazole by means of concentrated sulfuric acid methylbenzthiazolesulfonic acid, coupling,
the nitroazo dye thus obtained is reduced to the aminoazo dye and this is phosgenated together with 4-amino-2-chloro-4'-oxy-1,1'-azobenzene-3'-carboxylic acid.
The new dye forms a dark powder that dissolves in water with an olive color and colors cotton in brown olive tones with good wash and lightfastness using the one- or two-bath copper plating process.
Example: 18.2 parts of 5-nitro-2-aminabenzoic acid who diazotized in a known manner. On the other hand, 55 parts of 2- [4 '- (S "-oxynaphthyl- [2"] - aminophenyl)] - 6 - methylbenzthiazol- X,
6 "-disulfonic acid dissolved in 200 parts of water with the addition of 50 parts of 30 percent aqueous ammonia solution and at 0 the diazotized 5-nitro-2-aminobenzoic acid was added to this solution with stirring.
When the monoazo coupling has ended after more hours of stirring, the coupling mixture is heated to 50 without diluting and a concentrated aqueous solution of 42 parts of crystallized sodium sulphide is added with stirring. The reaction increases the temperature to 58. It is warmed to 75 for a further hour, then carefully acidified with hydrochloric acid and filtered.
The aminoazo dye formed is freed from sulfur residues by redissolving from weakly alkaline, dilute, aqueous solution and precipitated with sodium chloride, filtered off and dried.
14.1 parts of the aminoazo-dye obtained in this way are mixed with 6.3 parts of the sodium salt of 4-amino-2-chloro-4'-oxy-1,1'-azubenzene 3'-carboxylic acid in 2000 parts of water dissolved, 20 parts of sodium carbonate were added to the solution and phosgene was passed in at 30 to 35 with stirring.
One treats - replacing the used sodium carbonate - with phosgene until no free amino group can be detected any more. The unsymmetrical urea that is formed is filtered off, redissolved in an aqueous, sodium carbonate-alkaline solution and separated as the sodium salt with the aid of sodium chloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH295052T | 1950-08-11 | ||
| CH298035T | 1950-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH298035A true CH298035A (en) | 1954-04-15 |
Family
ID=25733558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH298035D CH298035A (en) | 1950-08-11 | 1950-08-11 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH298035A (en) |
-
1950
- 1950-08-11 CH CH298035D patent/CH298035A/en unknown
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