CH302018A - Process for the preparation of a vinyl sulfone dye. - Google Patents
Process for the preparation of a vinyl sulfone dye.Info
- Publication number
- CH302018A CH302018A CH302018DA CH302018A CH 302018 A CH302018 A CH 302018A CH 302018D A CH302018D A CH 302018DA CH 302018 A CH302018 A CH 302018A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- vinyl sulfone
- dye
- sulfone
- bromovinyl
- Prior art date
Links
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- UWLNKHDLVZEYKQ-UHFFFAOYSA-N 4-chloro-3-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC(S(O)(=O)=O)=CC=C1Cl UWLNKHDLVZEYKQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- -1 1-aminophenyl Chemical group 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 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
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Vinylsulfonfarbstoffes. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Herstellung eines Vinylsulfonfarbstoffes, welches dadurch ge- kennzeiehnet ist, dass man die Diazoniumv er- bindLing aus 1-Aminophenyl-3-(a-bromvinyl- sulfon) mit 1-(2'-Chlor-5'-sulfophenyl)-3-me- thyl-5-py razolon kuppelt.
<I>Beispiel:</I> 7,86 Gewichtsteile 1-Aminophenyl-3- (a- bromvinylsulfon) der Formel:
EMI0001.0018
werden in salzsaurer Lösung mit 30 Volumtei- 1en n-i\atriumnitritlösung diazotiert. Die Di- azolösung lässt man bei 0-8 C in eine Lösung von 10,5 Gewichtsteilen 1-(2'-Chlor-5'-sulfo- phenyl)-3-methyl-5-pyrazolon,
30 Volumteilen n-Natronlauge und 7 Gewichtsteilen kristalli siertem Natriumacetat in 150 Volumteilen Wasser einfliessen. Durch Zusatz von kristalli siertem Natriumaeetat wird dafür gesorgt, dass das Reaktionsgemisch nicht kongosauer wird. Nach beendeter Kupplung wird durch Erwär men auf 40-50 C der Farbstoff in Lösung gebracht. Durch Zugabe von Kochsalz wird dann der Farbstoff der folgenden Formel:
EMI0001.0034
abgeschieden, abgesaugt, mit Kochsalzlösung neutral gewaschen und getrocknet.
Das so erhaltene Produkt stellt ein gelbes Pulver dar, das Wolle in gelben Tönen von guten Echtheitseigenschaften. färbt.
Das als Diazokomponente verwendete 1- Aminophenyl - 3 - (a - bromv inylsulfon) kann durch Anlagerung von Brom an Phenyl-vinyl- sulfon, Abspaltung von Bromwasserstoff, Ni- trierung des Pheriyl-a-bromvinylsulfons in schwefelsaurer Lösung und 'Reduktion des 1- Nitrophenyl-3-(a-bromvinylsulfons) erhalten werden.
Das Amin schmilzt bei 94 C.
Process for the preparation of a vinyl sulfone dye. The subject of the present additional patent is a process for the production of a vinyl sulfone dye, which is characterized in that the diazonium compounds are made from 1-aminophenyl-3- (a-bromovinyl sulfone) with 1- (2'-chloro 5'-sulfophenyl) -3-methyl-5-pyrazolone couples.
<I> Example: </I> 7.86 parts by weight of 1-aminophenyl-3- (a-bromovinyl sulfone) of the formula:
EMI0001.0018
are diazotized in hydrochloric acid solution with 30 parts by volume of n-i \ atrium nitrite solution. The diazo solution is left at 0-8 ° C. in a solution of 10.5 parts by weight of 1- (2'-chloro-5'-sulfophenyl) -3-methyl-5-pyrazolone,
Pour 30 parts by volume of n-sodium hydroxide solution and 7 parts by weight of crystallized sodium acetate into 150 parts by volume of water. The addition of crystallized sodium acetate ensures that the reaction mixture does not become acidic to the Congo. After the coupling is complete, the dye is brought into solution by heating to 40-50 ° C. By adding table salt, the dye becomes the following formula:
EMI0001.0034
deposited, filtered off with suction, washed neutral with sodium chloride solution and dried.
The product obtained in this way is a yellow powder, the wool in yellow tones has good fastness properties. colors.
The 1-aminophenyl - 3 - (a - bromovynylsulfon) used as a diazo component can be obtained by adding bromine to phenyl vinyl sulfone, splitting off hydrogen bromide, nitrating the pheriyl a-bromovinyl sulfone in a sulfuric acid solution and reducing the 1- Nitrophenyl-3- (a-bromovinyl sulfone) can be obtained.
The amine melts at 94 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH302018T | 1951-07-16 | ||
| CH296001T | 1951-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302018A true CH302018A (en) | 1954-09-30 |
Family
ID=25733651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302018D CH302018A (en) | 1951-07-16 | 1951-07-16 | Process for the preparation of a vinyl sulfone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302018A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231171A (en) * | 1990-12-24 | 1993-07-27 | Basf Aktiengesellschaft | Reactive dyes having an allylsulfonyl or propargylesulfonyl group |
-
1951
- 1951-07-16 CH CH302018D patent/CH302018A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231171A (en) * | 1990-12-24 | 1993-07-27 | Basf Aktiengesellschaft | Reactive dyes having an allylsulfonyl or propargylesulfonyl group |
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