CH302019A - Process for the preparation of a vinyl sulfone dye. - Google Patents
Process for the preparation of a vinyl sulfone dye.Info
- Publication number
- CH302019A CH302019A CH302019DA CH302019A CH 302019 A CH302019 A CH 302019A CH 302019D A CH302019D A CH 302019DA CH 302019 A CH302019 A CH 302019A
- Authority
- CH
- Switzerland
- Prior art keywords
- vinyl sulfone
- preparation
- vinyl
- amino
- methylbenzene
- 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 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 6
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-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
- 239000004552 water soluble powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- QENFKLWBWWDGLL-UHFFFAOYSA-N 3-chloro-5-methyl-4-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=C(C)C=C(S(O)(=O)=O)C=C1Cl QENFKLWBWWDGLL-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- -1 sulfuric acid ester Chemical class 0.000 description 2
- WPGVQDHXOUAJBW-UHFFFAOYSA-N 2-methyl-5-nitrobenzenesulfonyl chloride Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(Cl)(=O)=O WPGVQDHXOUAJBW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007859 condensation product 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
- 239000000155 melt Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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)
- 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- kennzeichnet ist, dass man die Diazoniumver- bindung aus 1-Amino-4-methylbenzol-3-sulfon- säure- (2'-methoxy-5'-vinylsulfonyl)-phenyl- amid mit 1-(6'-Chlor-2'-methyl-4'-sulfophe- nyl)
-3-methyl-5-pyrazolon kuppelt. Beispiel: 3,8 Gewichtsteile 1-Amino-4-methylbenzol-3-sulfonsäure-(2'-methoxy-5'-vinylsulfonyl)- phenylamid der folgenden Formel:
EMI0001.0017
werden in salzsaurer Lösung mit 10 Volum- teilen n-Natriumnitritlösung in üblicher Weise diazotig #t. Die Diazolösung lässt man dann bei 5-10 CineineLösimgvon3,6Gewichtsteilen1- (6'-Chlor-2'-methyl-4'-sulfophenyl) -3-methyl- 5-pyr azolon 83 % ig und 8 Gewichtsteilen Ka- liumacetat in 100 Volumteilen Wasser einflie ssen.
Nach beendeter Kupplung wird der Vi- nylsulfonfarbstoff der folgenden Formel:
EMI0001.0035
mit Kaliumchlorid ausgesalzen, abgesaugt, mit einer Kaliumchloridlösung gewaschen und ge trocknet.
Das so erhaltene Produkt stellt ein gelbes, wasserlösliches Pulver dar, das Wolle in gel ben Tönen von guten Echtheitseigenschaften färbt.
Das als Diazokomponente verwendete 1 Amino-4-methylbenzol-3-sulfonsäure - (2'-meth- oxy-5'-vinylsulfonyl)-phenylamid kann wie folgt dargestellt werden:
1-Nitro-4-methylbenzol-3-sulfonsäurechlorid wird mit dem Alkalisalz des Schwefelsäure- esters aus 1-Amino-2-methoxyphenyl-5-ss-oxy- äthylsulfon kondensiert, das Kondensations produkt durch Behandeln mit einem Alkali in die Vinylsulfonverbindung übergeführt und die Nitrogruppe zur Aminogruppe reduziert. Das Amin sehmilzt bei 162-163 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 compound is obtained from 1-amino-4-methylbenzene-3-sulfonic acid- (2'-methoxy-5'- vinylsulfonyl) phenyl amide with 1- (6'-chloro-2'-methyl-4'-sulfophenyl)
-3-methyl-5-pyrazolone couples. Example: 3.8 parts by weight of 1-amino-4-methylbenzene-3-sulfonic acid (2'-methoxy-5'-vinylsulfonyl) phenylamide of the following formula:
EMI0001.0017
are diazotized in the usual way in hydrochloric acid solution with 10 parts by volume of n-sodium nitrite solution. The diazo solution is then allowed to dissolve 3.6 parts by weight of 1- (6'-chloro-2'-methyl-4'-sulfophenyl) -3-methyl-5-pyrazolone 83% and 8 parts by weight of potassium acetate in 100 parts by volume at 5-10 ° C Pour in water.
After the coupling is complete, the vinyl sulfone dye has the following formula:
EMI0001.0035
salted out with potassium chloride, filtered off with suction, washed with a potassium chloride solution and dried ge.
The product thus obtained is a yellow, water-soluble powder which dyes wool in yellow shades of good fastness properties.
The 1-amino-4-methylbenzene-3-sulfonic acid - (2'-methoxy-5'-vinylsulfonyl) -phenylamide used as the diazo component can be represented as follows:
1-Nitro-4-methylbenzene-3-sulfonic acid chloride is condensed with the alkali salt of the sulfuric acid ester from 1-amino-2-methoxyphenyl-5-ss-oxy ethyl sulfone, and the condensation product is converted into the vinyl sulfone compound by treatment with an alkali and the nitro group is reduced to the amino group. The amine melts at 162-163 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH296001T | 1951-07-16 | ||
| CH302019T | 1951-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302019A true CH302019A (en) | 1954-09-30 |
Family
ID=25733652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302019D CH302019A (en) | 1951-07-16 | 1951-07-16 | Process for the preparation of a vinyl sulfone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302019A (en) |
-
1951
- 1951-07-16 CH CH302019D patent/CH302019A/en unknown
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