CH296001A - Process for the preparation of a vinyl sulfone dye. - Google Patents
Process for the preparation of a vinyl sulfone dye.Info
- Publication number
- CH296001A CH296001A CH296001DA CH296001A CH 296001 A CH296001 A CH 296001A CH 296001D A CH296001D A CH 296001DA CH 296001 A CH296001 A CH 296001A
- Authority
- CH
- Switzerland
- Prior art keywords
- vinyl sulfone
- preparation
- dyes
- dye
- sulfone dye
- 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 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002964 rayon Substances 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
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000000987 azo dye 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 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)
Description
Verfahren zur Herstellung eines Vinylsulfonfarbstoües. 1:s wurde gefunden, dass man für das Färben und Drucken von natürlichen und synthetischen Fasern geeignete wertvolle Farbstoffe erhält., wenn man in das Molekül von sauren Farbstoffen oder deren Vorproduk ten die Atomgruppierung -S02-CR=CH.., worin R Wasserstoff, einen niedrig moleku laren Kohlenwasserstoffrest oder Halogen be deutet, ein- oder mehrmals einführt.
Saure Farbstoffe, die einmal oder mehrere Male die Urrappe -S02-CR=CH2 enthal ten, können verschiedenen Farbstoffklassen angehören. Beispielsweise können sie aus der Reihe der Azofarbstoffe, der Nitrofarbstoffe, der Anthrachinonfarbstoffe, der Triphenyl- methanfarbstoffe usw. stammen. Die Herstel lung der Ausgangsstoffe kann in verschiede ner Weise durchgeführt werden. Man kann z.
B. einen sauren Farbstoff oder ein Vorpro dukt, in die Sulfinsäure bzw. ihr Natriumsalz überführen und mit ss-Chlorätllylalkohol oder Ät.hylenoxyd bzw. deren Homologen zur Reak tion bringen. Aus den dabei erhältlichen (6-Oxäth@-lsulfonen kann man in üblicher Weise die Verbindungen reit, der Gruppe --S02-CR=CH2 herstellen und diese, wenn es sieh uni Vorprodlrkte handelt, mit reak tionsfähigen Komponenten, die gegebenen falls eine saure Gruppe enthalten können, ver einigen.
Verbindungen der vorliegenden Art können auch erhalten werden, indem man Ver bindungen mit der Gruppe -S-CR=CH2 oder -SO-CR=CH2 der Oxydation unter wirft. Schliesslich kann man auch von neu tralen Farbstoffen, die eine Vinylsulfon- gruppe enthalten, ausgehen und diese sulfo- nieren.
Die Farbstoffe haben besondere Affinität zu Wolle, Seide, Acetatseide, animalisierter Zellwolle, Polyamidfasern; sie können aber auch mit Vorteil, je nach der Struktur der zu Grunde liegenden Farbstoffmoleküle, zum Färben von Baumwolle, Zellwolle oder andern. Faserstoffen pflanzlichen Ursprungs verwen det werden.
Die Farbstoffe können wegen der sehr reaktionsfähigen Vinylsulfongruppe mit reaktionsfähigen Gruppen des Fasergutes in Reaktion treten. Sie können auch auf der Fa ser polymerisiert. bzw. durch Umsetzung mit Verbindungen, die mit Vinylsuliongruppen reagieren können, weiter kondensiert werden.
llan erhält auf diese Weise Färbungen und Drucke von ausgezeichneten Echtheitseigen- schaften.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Vinyl- sulfonfarbstoffes, welches dadurch gekenn zeichnet ist, dass man die Diazoniumverbin- dung aus 1-Aminophenyl-2-vinylsulfon in sau rem Medium mit 2 Amino-8-oxynaphtha-Iin-6- sulfonsäure kuppelt. Beispiel:
In eine Mischung aus 186 Gewichtsteilen Nitrosylschw efelsäure 20,5 %ig und 360 Ge- wichtsteilen Eisessig lässt man eine Lösung von 55,2 Gewichtsteilen 1-Aminophenyl-2- "inyIsillfon in 300 Volumteilen Eisessig lang-. sam einfliessen, wobei die Temperatur bis 15 G steigen kann.
Nach etwa zweistündigem Verrühren bei 15 C giesst. man :die Lösung auf Eis und zerstört die eventuell vorhandene freie salpetrige Säure mit Amidosulfonsäure. In die klare Diazolösung lässt man nun bei :5 bis 10 C 77,7 Gewichtsteile 2-Amino-8-oxy- naphthalin-6-sulfonsäure 92,1 a/oig, gelöst in 720 Volumteilen Wasser und 300 Volumteilen n-Natronlauge, einfliessen.
Nach beendeter Kupplung wird der Viiiylsulfonfarbstoff der folgenden Formel:
EMI0002.0020
mit Kochsalz ausgesalzen, abgesatugt, mit Kochsalzlösung neutral gewasehen und ge trocknet.
Das so erhaltene Produkt stellt ein dunkel rotes Pulver dar, das Wolle in lebhaften blaustiehigen Rottönen von ;-uten Eehtheits- eigenseha.ften färbt. '
Process for the preparation of a vinyl sulfone dye. 1: s it was found that valuable dyes suitable for dyeing and printing natural and synthetic fibers are obtained. If the atomic grouping -S02-CR = CH .., where R is hydrogen, is added to the molecule of acidic dyes or their preproducts , a low molecular hydrocarbon radical or halogen be means, one or more times.
Acid dyes that contain the primordial black horse -S02-CR = CH2 once or several times can belong to different dye classes. For example, they can come from the series of azo dyes, nitro dyes, anthraquinone dyes, triphenyl methane dyes, etc. The production of the starting materials can be carried out in various ways. You can z.
B. an acidic dye or a Vorpro product, converted into the sulfinic acid or its sodium salt and bring to reaction with ss-Chlorätllylalkohol or Ät.hylenoxyd or their homologues. From the (6-oxeth @ -lsulfones obtainable in this way) the compounds of the group --S02-CR = CH2 can be prepared in the usual way and these, if they are uni preliminary products, with reactive components, which may be acidic Group may contain agree.
Compounds of the present type can also be obtained by subjecting compounds with the group -S-CR = CH2 or -SO-CR = CH2 to oxidation. Finally, neutral dyes containing a vinyl sulfone group can also be used as a starting point and sulfonated.
The dyes have a special affinity for wool, silk, acetate silk, animalized rayon, polyamide fibers; however, they can also be used to advantage, depending on the structure of the underlying dye molecules, for dyeing cotton, rayon or other. Fibers of vegetable origin are used.
Because of the very reactive vinyl sulfone group, the dyes can react with reactive groups on the fiber material. They can also be polymerized on the fiber. or by reaction with compounds that can react with vinyl sulfone groups, condensed further.
In this way, llan receives dyeings and prints with excellent fastness properties.
The subject of the present patent is a process for the preparation of a vinyl sulfone dye, which is characterized in that the diazonium compound from 1-aminophenyl-2-vinyl sulfone in an acidic medium with 2 amino-8-oxynaphtha-Iin-6- sulfonic acid couples. Example:
A solution of 55.2 parts by weight of 1-aminophenyl-2- ”inylisolphone in 300 parts by volume of glacial acetic acid is allowed to slowly flow into a mixture of 186 parts by weight of nitrosyl sulfuric acid 20.5% and 360 parts by weight of glacial acetic acid, the temperature being 15 G can rise.
After stirring for about two hours at 15 C, it is poured. man: put the solution on ice and destroy any free nitrous acid with sulfamic acid. 77.7 parts by weight of 2-amino-8-oxynaphthalene-6-sulfonic acid 92.1 a / oig, dissolved in 720 parts by volume of water and 300 parts by volume of n-sodium hydroxide solution, are now allowed to flow into the clear diazo solution at: 5 to 10 ° C. .
After the coupling is complete, the vinyl sulfone dye has the following formula:
EMI0002.0020
Salted out with common salt, suctioned off, washed neutral with common salt solution and dried.
The product obtained in this way is a dark red powder which dyes wool in lively blue-tinged red tones with its own special properties. '
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH296001T | 1951-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296001A true CH296001A (en) | 1954-01-31 |
Family
ID=4489078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296001D CH296001A (en) | 1951-07-16 | 1951-07-16 | Process for the preparation of a vinyl sulfone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296001A (en) |
-
1951
- 1951-07-16 CH CH296001D patent/CH296001A/en unknown
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