CH233348A - Process for the preparation of a tetrakisazo dye. - Google Patents
Process for the preparation of a tetrakisazo dye.Info
- Publication number
- CH233348A CH233348A CH233348DA CH233348A CH 233348 A CH233348 A CH 233348A CH 233348D A CH233348D A CH 233348DA CH 233348 A CH233348 A CH 233348A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- weight
- parts
- amino
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 11
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- -1 aminoazo Chemical group 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 239000004552 water soluble powder Substances 0.000 claims description 2
- 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 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 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
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/28—Tetrazo dyes of the type A->B->K<-C<-D
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 229425. Verfahren zur Herstellung eines Tetrakisazofarbstoffes. Vorliegende Erfindung betrifft ein Ver fahren zur Herstellung eines T@trakisazofarb- otoffes. Das Verfahren besteht :darin, -dass man diazotierte 5-(4'-Aminobenzoylamino)-2- oxybenzol -1- carbonsäure mit 1-Amino - 2- m:
ethylbenzol vereinigt, den erhaltenen Aminoazofarbstoff weiterdiazotiert und mit dem symmetrischen Harnstoff aus 2-Amino- 5-oxynaphthalin-7-sulfonsäure kuppelt.
Der neue Farbstoff stellt ein :dunkles wasiserlösliches Pulver :dar, :das vegetabilische Fasern in blaustichig roten Tönen färbt.
Beispiel: 272 Gewichtsteile 5-(4'-Aminobenzoyl- 5 amino)-2-oxybenzol-l-carbonsäure werden in 4000 Gewichtsteilen Wasser unter Zusatz von 140 Gewichtsteilen Natriumcarbonat _ warm g g elöst. Nach Zugabe von 69 Gewichtsteilen Natriumnitrit wird abgekühlt und die Lösung o in 500
Gewichtsteile Salzsäure (d = 1,18) und 3500 Gewichtsteile Eis langsam einge rührt. Die gelbe Diazoniumverbindung fällt aus und wird nach 11/2 Stunden mit einer Lösung von 107 Gewichtsteilen 1-Amino-2- methylbenzol in 85 Gewichtsteilen Salzsäure (d =1.,18), verdünnt mit wenig Wasser, ver setzt.
Man stumpft mit etwa 700 Gewichts= teilen einer 30 % igen wässrigen Natrium- acetatlösung .ganz langsam ab und isoliert den Aminoazofarbstoff in üblicher Weise.
Zur weiteren Diazotierung wird das Zwi schenprodukt mit 4000 Gewichtsteilen Was iser erneut angeschlämmt. Es werden 69 Ge wichtsteile Natriumnitrit und 500 Gewichts teile Salzsäure (d = 1,18) nacheinander zu gefügt.
Man diazotiert 2 Stunden bei Zim- mertemperatur und trägt :die erhaltene dicke Paste in eine Lösung des Natriumsalzes von 252 Gewichtsteilen des symmetrischen Harn stoffes aus 2 -Amino - 5 - oxynaphthalin -7- sul- fonsäure ein. Die Kupplung wird durch langsame Zugabe einer Lösung von 70 Ge wichtsteilen Natriumcarbonat in Wasser be schleunigt und ist nach 2 ,Stunden beendet.
Der Farbstoff wird heiss mit wenig,Salz aus- gesalzen, filtriert und getrocknet. Der so her- gestellte Tetrakvsazofarbstoff stellt ein,dunk les wasserlösliches Pulver dar, das vegetabi lische Fasern in blaustichig roten Tönen an färbt. Die Nassechtheit der Färbungen wird durch Nachbehandlung mit Chromsalzen ver bessert, ohne dass sich der Farbton wesentlich ändert.
Additional patent to main patent No. 229425. Process for the production of a tetrakisazo dye. The present invention relates to a method for producing a T @ trakisazofarb- otoffes. The process consists of: -that diazotized 5- (4'-aminobenzoylamino) -2- oxybenzene -1-carboxylic acid with 1-amino - 2- m:
ethylbenzene combined, the aminoazo dye obtained further diazotized and coupled with the symmetrical urea from 2-amino-5-oxynaphthalene-7-sulfonic acid.
The new dye is a: dark washer-soluble powder: is,: that dyes vegetable fibers in bluish red tones.
Example: 272 parts by weight of 5- (4'-aminobenzoyl-5 amino) -2-oxybenzene-1-carboxylic acid are dissolved in 4000 parts by weight of water with the addition of 140 parts by weight of hot sodium carbonate. After adding 69 parts by weight of sodium nitrite, the mixture is cooled and the solution o in 500
Parts by weight of hydrochloric acid (d = 1.18) and 3500 parts by weight of ice are slowly stirred in. The yellow diazonium compound precipitates and is after 11/2 hours with a solution of 107 parts by weight of 1-amino-2-methylbenzene in 85 parts by weight of hydrochloric acid (d = 1., 18), diluted with a little water, ver sets.
About 700 parts by weight of a 30% strength aqueous sodium acetate solution are blunted very slowly and the aminoazo dye is isolated in the usual way.
For further diazotization, the inter mediate product is slurried again with 4000 parts by weight of water. 69 parts by weight of sodium nitrite and 500 parts by weight of hydrochloric acid (d = 1.18) are added one after the other.
The mixture is diazotized for 2 hours at room temperature and the thick paste obtained is added to a solution of the sodium salt of 252 parts by weight of the symmetrical urea from 2-amino-5-oxynaphthalene-7-sulphonic acid. The coupling is accelerated by the slow addition of a solution of 70 parts by weight of sodium carbonate in water and is complete after 2 hours.
The dye is salted out hot with a little salt, filtered and dried. The tetrakosazo dye produced in this way is a dark, water-soluble powder that stains vegetable fibers in bluish red tones. The wet fastness of the dyeings is improved by aftertreatment with chromium salts without the color shade changing significantly.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE233348X | 1941-06-09 | ||
| CH229425T | 1942-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH233348A true CH233348A (en) | 1944-07-15 |
Family
ID=25727352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH233348D CH233348A (en) | 1941-06-09 | 1942-05-28 | Process for the preparation of a tetrakisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH233348A (en) |
-
1942
- 1942-05-28 CH CH233348D patent/CH233348A/en unknown
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