CH217962A - Process for the preparation of a polyazo dye. - Google Patents
Process for the preparation of a polyazo dye.Info
- Publication number
- CH217962A CH217962A CH217962DA CH217962A CH 217962 A CH217962 A CH 217962A CH 217962D A CH217962D A CH 217962DA CH 217962 A CH217962 A CH 217962A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- weight
- parts
- amino
- preparation
- Prior art date
Links
- -1 polyazo Polymers 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- 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 5
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 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 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 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 description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052979 sodium sulfide 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
- C09B43/16—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
<B>Zusatzpatent</B> zum Hauptpatent Nr. 215147. Verfahren zur Herstellung eines Polyazofarbstoffes. Es wurde gefunden, dass man einen neuen Polyazofarbstoff erhalten kann, wenn man auf 1 Mol Cyanurchlorid 2 Mol des Monoazofarbstoffes, der erhalten wird durch Reduzieren der Nitrogruppe zur Aminogruppe in dem Produkt,
das selbst erhalten wird durch Einwirkenlassen von 4-Nitrobenzoyl- ehlorid auf .den Monoazofarbstoff aus @diazo- tierter 3-Amino-2-oxy-l-carboxybenzol-5-sul- fonsäure und 1-Methyl-3-aminobenzol und 1 Mol 4-Amino-4'-oxyazobenzol-3'-carbon- säure einwirken lässt.
Der neue Polyazofarb- stoff färbt Baumwolle in schwach alkali schem Bade bei Gegenwart von Kupfersulfat und weinsaurem Natrium in waschechten, rotstichig gelben Tönen an.
<I>Beispiel:</I> 70,2 Gewichtsteile des Monoazofarbstoffes aus diazotierter 3-Amino-2-oxy-l-aarboxy- benzol-5-sulfonsäurL- und 1-Methyl-3-amino- benzol werden als Natriumsalz in 500 Ge wichtsteilen Wasser unter Zusatz von 27 Ge- wichtsteilen Natriumacetat gelöst. Diese Lö sung wird bei etwa<B>60'</B> mit 39 Gewichts teilen 4-Nitrobenzoylchlorid, die mit 10 Ge wichtsteilen Aceton versetzt wurden, behan delt.
Man reduziert das Nitrobenzoylprodukt mit 84 Gewichtsteilen kristallisiertem Na triumsulfid, die in 150 Gewichtsteilen Was ser gelöst wurden, bei<B>65-70'</B> zum Amino- benzoylprodukt.
94 Gewichtsteile des abgeschiedenen Re duktionsproduktes werden als neutrale Lö sung in 1.000 Gewichtsteilen Wasser zu einer Anschlämmung von 18,4 Gewichtsteilen Cyanurchlorid in 500 Gewichtsteilen kaltem Wassergegeben. Die bei der Kondensation entstehende Salzsäure wird durch" die entspre chende Menge Natriumearbonat neutralisiert. Die Temperatur wird langsam auf 40' ge steigert und 2 Stunden bei 40-45 gehalten.
Hernach werden 27,8 Gewichtsteile 4-amino- 4'-oxy-1,1'-azobenzol-3'-carbonsaures Na trium, :die in 500 Gewichtsteilen Wasser ge löst wurden, zum Dikondensationsprodukt ge- geben und die Temperatur während 3 Stun den auf 80 gehalten. Das tertiäre Konden sationsprodukt ist nach dieser Zeit gebildet. Es wird mittels Natriumchlorid abgeschieden und getrocknet.
<B> Additional patent </B> to main patent No. 215147. Process for the production of a polyazo dye. It has been found that a new polyazo dye can be obtained if, for 1 mole of cyanuric chloride, 2 moles of the monoazo dye, which is obtained by reducing the nitro group to the amino group in the product,
which itself is obtained by allowing 4-nitrobenzoyl chloride to act on the monoazo dye from @ diazo-tated 3-amino-2-oxy-1-carboxybenzene-5-sulphonic acid and 1-methyl-3-aminobenzene and 1 mol of 4 -Amino-4'-oxyazobenzene-3'-carboxylic acid can act.
The new polyazo dye dyes cotton in a weakly alkaline bath in the presence of copper sulfate and tartrate of sodium in washfast, reddish yellow tones.
<I> Example: </I> 70.2 parts by weight of the monoazo dye from diazotized 3-amino-2-oxy-1-aarboxy-benzene-5-sulfonic acid and 1-methyl-3-aminobenzene are used as the sodium salt in 500 Parts by weight of water with the addition of 27 parts by weight of sodium acetate dissolved. This solution is treated at about <B> 60 '</B> with 39 parts by weight of 4-nitrobenzoyl chloride to which 10 parts by weight of acetone have been added.
The nitrobenzoyl product is reduced with 84 parts by weight of crystallized sodium sulfide, which were dissolved in 150 parts by weight of water, at 65-70 'to the amino benzoyl product.
94 parts by weight of the separated reduction product are added as a neutral solution in 1,000 parts by weight of water to a slurry of 18.4 parts by weight of cyanuric chloride in 500 parts by weight of cold water. The hydrochloric acid formed during the condensation is neutralized with the appropriate amount of sodium carbonate. The temperature is slowly increased to 40 ° and kept at 40-45 for 2 hours.
Thereafter, 27.8 parts by weight of 4-amino-4'-oxy-1,1'-azobenzene-3'-carboxylic acid sodium: which were dissolved in 500 parts by weight of water, are added to the dicondensation product and the temperature is maintained for 3 hours kept at 80. The tertiary condensation product is formed after this time. It is precipitated using sodium chloride and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215147T | 1939-07-12 | ||
| CH217962T | 1939-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217962A true CH217962A (en) | 1941-11-15 |
Family
ID=25725685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217962D CH217962A (en) | 1939-07-12 | 1939-07-12 | Process for the preparation of a polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH217962A (en) |
-
1939
- 1939-07-12 CH CH217962D patent/CH217962A/en unknown
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