CH308781A - Process for the preparation of a new disazo dye. - Google Patents
Process for the preparation of a new disazo dye.Info
- Publication number
- CH308781A CH308781A CH308781DA CH308781A CH 308781 A CH308781 A CH 308781A CH 308781D A CH308781D A CH 308781DA CH 308781 A CH308781 A CH 308781A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- new
- methyl
- disazo dye
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- YNWUKJSMSIFJTD-UHFFFAOYSA-N ClC1=C(C=C(C(=C1)Cl)S(=O)(=O)O)N1N=C(CC1=O)C Chemical compound ClC1=C(C=C(C(=C1)Cl)S(=O)(=O)O)N1N=C(CC1=O)C YNWUKJSMSIFJTD-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000007935 neutral effect Effects 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
- 210000002268 wool Anatomy 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 3
- 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 306377. Verfahren zur Herstellung eines neuen Disazofarbstoffes. Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung eines neuen Disazofarbstoffes, der eine ausgezeich nete Echtheit und ein ausgezeichnetes Auf ziehvermögen aufweist, für tierische Fasern.
Der neue Disazofarbstoff wird erfindungs gemäss so erhalten, dass man 1 Mol tetrazotier- tes 3,3'-Diamino-6'-methyl-1'-N-ss-2",4"-di- ehlorphenoxyäthylbenzanilid mit 2 Mol 1-(2', 4'- Dichlor - 5'-sulfophenyl) -3-methyl-5-pyra.zo- lon kuppelt.
Das als Ausgangsmaterial verwendete sub stituierte Benzanilid ist eine neue Verbindung vom Smp. 143-144 C, die durch Kondensa tion von 4-Nitro-2-N-ss-2',4'-dichlorphenoxy- äthyltoluidin und m-Nitrobenzoylchlorid und anschliessende Reduktion der Nitrogruppen erhalten werden kann. Das substituierte To luidin kann durch Umsetzung von 4-Nitro-2- aminotoluol mit ss-2,4-Dichlorphenoxyäthyl- bromid in Gegenwart eines säurebindenden Mittels erhalten werden.
Das f-2,4-Dichlor- phenoxyäthylbromid kann durch Umsetzung von 2,4-Dichlorphenol mit Äthylendibromid in Gegenwart von Alkali erhalten werden.
In dem folgenden Beispiel sind die ange gebenen Teile gewichtsmässig zu verstehen. <I>Beispiel:</I> 43 Teile 3,3'-Diamino-6'-methyl-1'-N-ss-2", 4"-dichlor-phenoxyäthylbenzanilid (Smp. 143 bis 144 C) werden in einem Gemisch von 700 Teilen Wasser und 50 Teilen 3611/oiger wäs- seriger Salzsäure gelöst. Der auf 10 C abge kühlten Lösung wird hierauf eine Lösung von 13,8 Teilen Natriumnitrit in 100 Teilen Was ser zugesetzt.
Die so erhaltene Lösung wird hierauf im Verlaufe von 15-20 Minuten in eine gerührte Lösung von 72 Teilen des Na triumsalzes des 1- (2',4'-Dichlor-5'-sulfophe- nyl) -3-methyl-5-pyrazolons in 1000 Teilen Wasser, welcher 54 Teile Natriumacetatkri- stalle zugesetzt worden sind, bei 15-20 C ein getragen. Dem Gemisch werden hierauf im Verlaufe von 45 Minuten langsam 400 Teile Natriumchlorid zugesetzt, worauf das Gemisch auf 50-60 C erhitzt und filtriert wird. Der feste Rückstand wird dann getrocknet.
Der neue Farbstoff bildet ein gelbes Pul ver, das sich in heissem Wasser unter Bildung einer rötlichgelb gefärbten Lösung und in konzentrierter Schwefelsäure unter Bildung einer gelb gefärbten Lösung löst. Der Farb stoff färbt Wolle aus einem neutralen oder schwach sauren Färbebad in leuchtend gel ben Farbtönen. Die Färbungen weisen sehr. gute Wasch-, Walk-, Schweiss- und Lichtecht heit auf.
Additional patent to main patent No. 306377. Process for the production of a new disazo dye. The present invention relates to a process for the preparation of a new disazo dye, which has an excellent fastness and an excellent absorbability, for animal fibers.
The new disazo dye is obtained according to the invention in such a way that 1 mol of tetrazotized 3,3'-diamino-6'-methyl-1'-N-ss-2 ", 4" -di- ehlorphenoxyäthylbenzanilid with 2 mol 1- ( 2 ', 4'-dichloro-5'-sulfophenyl) -3-methyl-5-pyra.zolone couples.
The substituted benzanilide used as the starting material is a new compound with a melting point of 143-144 C, which is produced by condensation of 4-nitro-2-N-ss-2 ', 4'-dichlorophenoxy- ethyltoluidine and m-nitrobenzoyl chloride and subsequent reduction the nitro groups can be obtained. The substituted toluidine can be obtained by reacting 4-nitro-2-aminotoluene with β-2,4-dichlorophenoxyethyl bromide in the presence of an acid-binding agent.
The f-2,4-dichlorophenoxyethyl bromide can be obtained by reacting 2,4-dichlorophenol with ethylene dibromide in the presence of alkali.
In the following example, the specified parts are to be understood in terms of weight. <I> Example: </I> 43 parts of 3,3'-diamino-6'-methyl-1'-N-ss-2 ", 4" -dichlorophenoxyethylbenzanilide (melting point 143 to 144 C) are in one Mixture of 700 parts of water and 50 parts of 3611 / oiger aqueous hydrochloric acid dissolved. The solution, cooled to 10 C, is then added to a solution of 13.8 parts of sodium nitrite in 100 parts of water.
The solution thus obtained is then poured into a stirred solution of 72 parts of the sodium salt of 1- (2 ', 4'-dichloro-5'-sulfophenyl) -3-methyl-5-pyrazolone in the course of 15-20 minutes in 1000 parts of water, to which 54 parts of sodium acetate crystals have been added, at 15-20 ° C. 400 parts of sodium chloride are then slowly added to the mixture over the course of 45 minutes, whereupon the mixture is heated to 50-60 ° C. and filtered. The solid residue is then dried.
The new dye forms a yellow powder that dissolves in hot water to form a reddish yellow solution and in concentrated sulfuric acid to form a yellow solution. The dye dyes wool from a neutral or weakly acidic dye bath in bright yellow shades. The colorations are very wise. good fastness to washing, fulling, perspiration and light.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB308781X | 1951-05-25 | ||
| CH306377T | 1952-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308781A true CH308781A (en) | 1955-07-31 |
Family
ID=25735115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308781D CH308781A (en) | 1951-05-25 | 1952-05-24 | Process for the preparation of a new disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308781A (en) |
-
1952
- 1952-05-24 CH CH308781D patent/CH308781A/en unknown
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