CH308785A - Process for the preparation of a new disazo dye. - Google Patents
Process for the preparation of a new disazo dye.Info
- Publication number
- CH308785A CH308785A CH308785DA CH308785A CH 308785 A CH308785 A CH 308785A CH 308785D A CH308785D A CH 308785DA CH 308785 A CH308785 A CH 308785A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- yellow
- new
- preparation
- solution
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 11
- 239000000975 dye Substances 0.000 claims description 10
- 239000001361 adipic acid Substances 0.000 claims description 6
- 235000011037 adipic acid Nutrition 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- FHXUYFKYRBLZJU-UHFFFAOYSA-N 3-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=CC(S(O)(=O)=O)=C1 FHXUYFKYRBLZJU-UHFFFAOYSA-N 0.000 claims description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005695 Ammonium acetate Substances 0.000 claims description 2
- 235000019257 ammonium acetate Nutrition 0.000 claims description 2
- 229940043376 ammonium acetate Drugs 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 210000004243 sweat Anatomy 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 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
- JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound 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
- 239000002253 acid Substances 0.000 description 1
- -1 adipic acid halide Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 238000003756 stirring 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
<B>Zusatzpatent</B> zum Hauptpatent Nr. 306378. Verfahren zur Herstellung eines neuen Disazofarbstoffes. Gegenstand der Erfindung ist ein Ver fahren zur Herstellung eines neuen Disazo- farbstoffes.
Dieser neue Farbstoff wird erfindungs gemäss so erhalten, dass man 1 Mol tetrazo- tiertes Adipinsäure-bis (4-amino-N-ss-phenoxy- äthylanilid) mit 2 Mol 1-(3'-Sulfophenyl)-3- methyl-5-pyrazolon kuppelt.
Das Adipinsäure-bis(4-amino-N-ss-phen- oxyäthylanilid) ist. eine neue Verbindung vom Smp. 158-159 C, die durch Umsetzung von 4-Nitro-N-ss-phenoxyäthylanilin mit Adipin- säureehloiid in trockenem Toluol, wobei Adi- pinsäure-bis (4-nitro-N-ss-phenoxyäthylanilid) entsteht, dessen Nitrogruppe mittels Eisen und Salzsäure in Äthanol oder in wässerigem Biitanol zu einer Aminogruppe reduziert wird, erhalten werden kann.
4-Nitro-N-ss-phen- oxyäthylanilin kann durch Umsetzung von p-Nitroanilin und ss-Phenoxyäthylbromid in Gegenwart eines säurebindenden Mittels er halten werden. ss-Phenoxyäthylbromid kann durch Umsetzung von Phenol und Äthylen- dibromid erhalten. werden.
Im folgenden Beispiel sind die Teile ge wichtsmässig angegeben. <I>Beispiel:</I> Man löst 56,6 Teile Adipinsäure-bis(4- amino-N-ss-phenoxyäthylanilid) in 700 Teilen Wasser und versetzt die Lösung mit 50 Tei len 361/oiger wässeriger Salzsäure. Der erhal tenen Lösung wird bei 15-20 C eine Lösung von 13,8 Teilen Natriumnitrit in 100 Teilen Wasser zugesetzt.
Die auf diese Weise erhal tene Lösung wird hierauf im Verlaufe von 20 Minuten unter Rühren in eine Lösung von 56,4 Teilen des Natriumsalzes des 1-(3'-Sulfo- phenyl)-3-methyl-5-pyrazolons in 1500 Teilen Wasser, die zudem noch 54 Teile Natriumace- tatkristalle und 120 Teile Natriumchlorid ent hält und eine Temperatur von 15-20 C auf weist, eingetragen. Wenn die Kupplung be endet ist, wird das Gemisch auf 50 C erhitzt und hierauf filtriert. Der Rückstand wird bei 50-60 C getrocknet.
Der neue Farbstoff ist ein gelbes Pulver, das sich in warmem Wasser unter Bildung einer rötlichgelb gefärbten Lösung und in konz. Schwefelsäure unter Bildung einer grün lichgelb gefärbten Lösung löst. Dieser Farb stoff färbt Wolle aus einem Ammoniumacetat (2 '/o, bezogen auf das Gewicht des zu färben den Materials) enthaltenden Färbebad in röt- lichgel.ben Farbtönen. Die Färbungen besitzen eine sehr gute Echtheit gegen wiederholtes Waschen, Walken, Schweiss und Licht.
<B> Additional patent </B> to main patent No. 306378. Process for the production of a new disazo dye. The invention relates to a process for the production of a new disazo dye.
This new dye is obtained according to the invention in such a way that 1 mole of tetrazolated adipic acid bis (4-amino-N-ss-phenoxy-ethylanilide) with 2 moles of 1- (3'-sulfophenyl) -3-methyl-5- pyrazolone couples.
The adipic acid bis (4-amino-N-ss-phenoxyethylanilide) is. a new compound with a melting point of 158-159 C, which is formed by reacting 4-nitro-N-ss-phenoxyethylaniline with adipic acid halide in dry toluene, whereby adipic acid bis (4-nitro-N-ss-phenoxyethylanilide) is formed whose nitro group is reduced to an amino group by means of iron and hydrochloric acid in ethanol or in aqueous biitanol.
4-Nitro-N-ß-phenoxyethylaniline can be obtained by reacting p-nitroaniline and ß-phenoxyethyl bromide in the presence of an acid-binding agent. SS-Phenoxyäthylbromid can be obtained by reacting phenol and ethylene dibromide. will.
In the following example the parts are given by weight. <I> Example: </I> 56.6 parts of adipic acid bis (4-amino-N-ss-phenoxyethylanilide) are dissolved in 700 parts of water, and the solution is treated with 50 parts of 361% aqueous hydrochloric acid. A solution of 13.8 parts of sodium nitrite in 100 parts of water is added to the solution obtained at 15-20.degree.
The solution obtained in this way is then in the course of 20 minutes with stirring in a solution of 56.4 parts of the sodium salt of 1- (3'-sulfophenyl) -3-methyl-5-pyrazolone in 1500 parts of water, which also contains 54 parts of sodium acetate crystals and 120 parts of sodium chloride and has a temperature of 15-20 C, entered. When the coupling has ended, the mixture is heated to 50 ° C. and then filtered. The residue is dried at 50-60C.
The new dye is a yellow powder that dissolves in warm water to form a reddish-yellow solution and in conc. Sulfuric acid to form a greenish yellow colored solution. This dye dyes wool from a dyebath containing ammonium acetate (2%, based on the weight of the material to be dyed) in reddish-yellow shades. The dyeings have very good fastness to repeated washing, tumbling, sweat and light.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB308785X | 1951-06-06 | ||
| CH306378T | 1952-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308785A true CH308785A (en) | 1955-07-31 |
Family
ID=25735119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308785D CH308785A (en) | 1951-06-06 | 1952-06-05 | Process for the preparation of a new disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308785A (en) |
-
1952
- 1952-06-05 CH CH308785D patent/CH308785A/en unknown
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