CH220431A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH220431A CH220431A CH220431DA CH220431A CH 220431 A CH220431 A CH 220431A CH 220431D A CH220431D A CH 220431DA CH 220431 A CH220431 A CH 220431A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- mole
- mol
- acid
- aniline
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 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 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 210000002268 wool Anatomy 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
- 229920000742 Cotton Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man einen neuen Azofarbstoff erhält, wenn man 1 Mol 1-Amino-8-oxynaphthalin - 3,6 - disulfonsäure, 1 Mol Cyanurchlorid, 1 Mol der diazotierten 4-Amino-4'-oxvazobenzol - 3,3' - dicarbonsäure,
1 Mol 4-Amino-4'- oxyazobenzol - 3'- carbon- säure und 1 Mol Anilin derart aufeinander einwirken lässt, dass die Diazoverbindung in 7-Stellung des Naphthalinrestes eingreift, und dass je 1 Halogenatom des Cyanurchlo- rids sich mit der Aminogruppe des Naphtha linderivates, der 4-Amino-4'-oxyazobenzol-3'- earbonsäure und des Anilins umsetzt.
Der neue Farbstoff stellt ein dunkles Pulver dar, das Baumwolle in schwach alkalischem Bade bei Gegenwart von Kupfersulfat und wein saurem Natrium in waschechten blaugrünen Tönen färbt.
Beispiel: 30,1 Gewichtsteile der 4-Amino-4'-oxy- azobenzol-3,3'-dicarbonsäure werden in 500 Gewichtsteilen Wasser mit 28 Gewichtsteilen 30%iger Salzsäure und 6,9 Gewichtsteilen Natriumnitrit bei 15 bis 20' diazotiert. Nach zwei Stunden wird die gebildete Diazover- bindung filtriert und der Filterrückstand in wässeriger Suspension zu einer 10%igen wässerigen Lösung von 74,5 Gewichtsteilen des tertiären Kondensationsproduktes aus 1 Mol Cyanurchlorid,
1 Mol 1-Amino-8-oxy- naphthalin-3,6-disulfonsäure, 1 Mol 4-Amino- 4'-oxyazobenzol-3'-carbonsäure und 1 Mol Anilin, die mit 50 Gewichtsteilen 30 % iger Ammoniaklösung versetzt und mit Eis auf 0 gekühlt wurden, gegeben. Der gebildete Farbstoff wird nach 6 Stunden mittels Na triumchlorid abgeschieden und getrocknet.
Process for the preparation of an azo dye. It has been found that a new azo dye is obtained if 1 mole of 1-amino-8-oxynaphthalene - 3,6 - disulfonic acid, 1 mole of cyanuric chloride, 1 mole of the diazotized 4-amino-4'-oxvazobenzene - 3,3 ' - dicarboxylic acid,
1 mole of 4-amino-4'-oxyazobenzene-3'-carboxylic acid and 1 mole of aniline can act on one another in such a way that the diazo compound engages in the 7-position of the naphthalene radical, and that every 1 halogen atom of the cyanuric fluoride combines with the amino group of the naphtha linderivates, which converts 4-amino-4'-oxyazobenzene-3'-carboxylic acid and aniline.
The new dye is a dark powder that dyes cotton in a weakly alkaline bath in the presence of copper sulfate and acidic sodium in washfast blue-green tones.
Example: 30.1 parts by weight of 4-amino-4'-oxyazobenzene-3,3'-dicarboxylic acid are diazotized in 500 parts by weight of water with 28 parts by weight of 30% strength hydrochloric acid and 6.9 parts by weight of sodium nitrite at 15 to 20 '. After two hours, the diazo compound formed is filtered and the filter residue in aqueous suspension to a 10% aqueous solution of 74.5 parts by weight of the tertiary condensation product of 1 mol of cyanuric chloride,
1 mole of 1-amino-8-oxynaphthalene-3,6-disulfonic acid, 1 mole of 4-amino-4'-oxyazobenzene-3'-carboxylic acid and 1 mole of aniline, which is mixed with 50 parts by weight of 30% ammonia solution and with ice were cooled to 0, given. The dye formed is deposited after 6 hours by means of sodium chloride and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH220431T | 1941-06-16 | ||
| CH217492T | 1941-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH220431A true CH220431A (en) | 1942-03-31 |
Family
ID=25726035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH220431D CH220431A (en) | 1941-06-16 | 1941-06-16 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH220431A (en) |
-
1941
- 1941-06-16 CH CH220431D patent/CH220431A/en unknown
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