DE4032923A1 - New reactive sulpho:phenyl:azo-pyridone dyes - Google Patents
New reactive sulpho:phenyl:azo-pyridone dyesInfo
- Publication number
- DE4032923A1 DE4032923A1 DE19904032923 DE4032923A DE4032923A1 DE 4032923 A1 DE4032923 A1 DE 4032923A1 DE 19904032923 DE19904032923 DE 19904032923 DE 4032923 A DE4032923 A DE 4032923A DE 4032923 A1 DE4032923 A1 DE 4032923A1
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- pyridone
- following formula
- acid
- substd
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/36—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to some other heterocyclic ring
- C09B62/40—Azo dyes
- C09B62/405—Monoazo dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Description
Gegenstand der Erfindung sind Monoazoreaktivfarbstoffe, die in Form der freien Säure der Struktur (1)The invention relates to monoazoreactive dyes in the form of the free Acidity of structure (1)
entsprechen, wobeicorrespond with
mit der Maßgabe, daß der Pyridonrest mit wenigstens einem Sulfato- oder Sulfonsäurerest substituiert ist.with the proviso that the pyridone residue with at least one sulfato or Sulfonic acid residue is substituted.
Hervorzuheben sind Farbstoffe der Struktur (2)Of special note are dyes of the structure (2)
wobei
R₂ = CH₂SO₃H, SO₃H und
R₃ = H, CH₃ oder C₂H₅,in which
R₂ = CH₂SO₃H, SO₃H and
R₃ = H, CH₃ or C₂H₅,
sowie Farbstoffe der Struktur (3)and structure dyes (3)
wobeiin which
Besonders bevorzugt sind Farbstoffe der Struktur (4)Dyes of the structure (4) are particularly preferred
wobeiin which
R₃ = H, CH₃ oder C₂H₅.R₃ = H, CH₃ or C₂H₅.
Gegenstand der Erfindung ist auch das Verfahren zur Herstellung der Reaktivfarbstoffe der Struktur (1), indem manThe invention also relates to the process for producing the Reactive dyes of structure (1) by
-
a) Aminoazofarbstoffe der Struktur (5),
wobei
R₁, R₂ und R₃ die anfangs genannte Bedeutung haben,
mit 2,3-Dichlor-6-(bzw. 5-)chinoxalincarbonsäurechlorid in Gegenwart säurebindender Mittel kondensiert, oder abera) aminoazo dyes of structure (5), in which
R₁, R₂ and R₃ have the meaning given above,
condensed with 2,3-dichloro-6- (or. 5-) quinoxaline carboxylic acid chloride in the presence of acid-binding agents, or else -
b) das Monokondensationsprodukt aus 2,4-Diaminobenzolsulfonsäure und 2,3-
Dichlor-6-(bzw. 5-)chinoxalincarbonsäurechlorid in üblicher Weise diazotiert
und auf sulfato- oder sulfogruppenhaltige Pyridone der Struktur (6) oder
solche der Struktur (7),
wie sie z. B. in der DE-OS 21 62 858 aufgeführt sind,
wobei
R₁, R₂ und R₃ die anfangs genannte Bedeutung zukommt,
kuppelt.b) the monocondensation product of 2,4-diaminobenzenesulfonic acid and 2,3-dichloro-6- (or. 5) quinoxalinecarboxylic acid chloride is diazotized in a conventional manner and on pyridones of structure (6) or those of structure (7) containing sulfato or sulfo groups, as they e.g. B. are listed in DE-OS 21 62 858,
in which
R₁, R₂ and R₃ have the meaning given above,
couples.
Die Aminoazoverbindungen der Struktur (5) erhält man durch Kuppeln von diazotierter 4-Acylamino-2-aminobenzolsulfonsäure auf Pyridone der Struktur (6) und (7) und anschließende saure Verseifung der resultierenden Acylaminoazoverbindungen der Struktur (8).The aminoazo compounds of structure (5) are obtained by coupling diazotized ones 4-acylamino-2-aminobenzenesulfonic acid on pyridones of structure (6) and (7) followed by acidic saponification of the resulting acylaminoazo compounds the structure (8).
Ausgewählte Beispiele für sulfogruppenhaltige Pyridone der Struktur (6) und (7) sind u. a.:Selected examples of sulfo-containing pyridones of structure (6) and (7) are u. a .:
3-Aminocarbonyl-1,4-dimethyl-5-sulfomethyl-6-hydroxy-2-pyridon,
3-Aminocarbonyl-1-ethyl-4-methyl-5-sulfomethyl-6-hydroxy-2-pyridon,
1,4-Dimethyl-5-sulfo-6-hydroxy-2-pyridon,
4-Methyl-5-sulfo-(4′-sulfobenzyl)-6-hydroxy-2-pyridon,
1-Methyl-4-sulfomethyl-6-hydroxy-2-pyridon,
1-Ethyl-3,4-bis-(sulfomethyl)-6-hydroxy-2-pyridon,
4-Methyl-1-(2′-sulfoethyl)-6-hydroxy-2-pyridon,
4-Methyl-1-(2′-sulfatoethyl)-6-hydroxy-2-pyridon,
4-Methyl-1-(2′-sulfatoethyl)-3-sulfo-6-hydroxy-2-pyridon,
3-Chlor-4-methyl-1-(2′-sulfoethyl)-6-hydroxy-2-pyridon,
3,4-Dimethyl-1-(2′-sulfatoethyl)-6-hydroxy-2-pyridon,
4-Carboxy-3-sulfomethyl-6-hydroxy-2-pyridon.3-aminocarbonyl-1,4-dimethyl-5-sulfomethyl-6-hydroxy-2-pyridone,
3-aminocarbonyl-1-ethyl-4-methyl-5-sulfomethyl-6-hydroxy-2-pyridone,
1,4-dimethyl-5-sulfo-6-hydroxy-2-pyridone,
4-methyl-5-sulfo- (4'-sulfobenzyl) -6-hydroxy-2-pyridone,
1-methyl-4-sulfomethyl-6-hydroxy-2-pyridone,
1-ethyl-3,4-bis (sulfomethyl) -6-hydroxy-2-pyridone,
4-methyl-1- (2'-sulfoethyl) -6-hydroxy-2-pyridone,
4-methyl-1- (2'-sulfatoethyl) -6-hydroxy-2-pyridone,
4-methyl-1- (2′-sulfatoethyl) -3-sulfo-6-hydroxy-2-pyridone,
3-chloro-4-methyl-1- (2'-sulfoethyl) -6-hydroxy-2-pyridone,
3,4-dimethyl-1- (2'-sulfatoethyl) -6-hydroxy-2-pyridone,
4-carboxy-3-sulfomethyl-6-hydroxy-2-pyridone.
Die Azoreaktivfarbstoffe der Struktur (1) färben hydroxylgruppenhaltiges Fasermaterial, insbesondere Baumwolle, in brillanten gelben Nuancen. Die Farbstoffe zeigen ein hervorragendes Aufziehvermögen und liefern hohe Fixierausbeuten. Das Echtheitsniveau der Färbungen ist ausgezeichnet.The azo reactive dyes of structure (1) dye those containing hydroxyl groups Fiber material, especially cotton, in brilliant yellow shades. The Dyes show excellent absorbency and deliver high Fixing yields. The level of authenticity of the dyeings is excellent.
Die oben angegebenen Formeln sind die der freien Säuren. Im allgemeinen erhält man bei der Synthese Salze, auf die sich die vorliegende Erfindung ebenfalls bezieht, im allgemeinen die Alkalisalze, insbesondere die Na- oder Li-Salze und verwendet die Farbstoffe auch in dieser Form zum Färben. The formulas given above are those of free acids. Generally receives one in the synthesis salts on which the present invention also relates relates, generally the alkali salts, in particular the Na or Li salts and also uses the dyes in this form for dyeing.
33,4 g 4-Acetamino-2-aminobenzolsulfonsäure werden in bekannter Weise unter sauren Bedingungen mit Natriumnitritlösung diazotiert. Zur fertigen Diazoniumsalzsuspension fügt man 39,5 g 3-Aminocarbonyl-1,4-dimethyl-5-sulfomethyl-6- hydroxy-2-pyridon und stellt den pH der Reaktionsmischung langsam mit 20%iger Sodalösung auf pH 7,5 und hält ihn konstant. Nach 30 Minuten ist die Kupplung beendet.33.4 g of 4-acetamino-2-aminobenzenesulfonic acid are added in a known manner acidic conditions diazotized with sodium nitrite solution. For the finished diazonium salt suspension 39.5 g of 3-aminocarbonyl-1,4-dimethyl-5-sulfomethyl-6- are added hydroxy-2-pyridone and slowly adjust the pH of the reaction mixture to 20% Soda solution to pH 7.5 and keeps it constant. After 30 minutes the clutch is out completed.
Die Farbstoffmischung (Volumen ca. 700 ml) wird nun mit 100 ml konzentrierter Salzsäure sauer gestellt und für 1 Stunde auf 95-98°C erwärmt. Dabei resultiert kurzzeitig eine tiefgelbe Lösung. Gegen Ende der Verseifung fällt die Aminoazoverbindung in kristalliner Form aus. Es wird auf Raumtemperatur abgekühlt und nach Zugabe von 40 g Kochsalz abgesaugt.The dye mixture (volume approx. 700 ml) is now concentrated with 100 ml Hydrochloric acid acidified and warmed to 95-98 ° C for 1 hour. The result is briefly a deep yellow solution. The aminoazo compound falls towards the end of the saponification in crystalline form. It is cooled to room temperature and after the addition of 40 g of sodium chloride.
Die feuchte gelbe Paste wird in 400 ml Wasser angerührt und mit Lithiumhydroxidlösung bei pH 6,5 gelöst. Die auf 45°C erwärmte Lösung wird mit 44 g frisch sublimiertem 2,3-Dichlor-6-chinoxalincarbonsäurechlorid versetzt. Die Acylierungsreaktion hält man nun durch Zudosieren von Sodalösung konstant zwischen 6,5 und 7,0. Die Temperatur beträgt weiterhin 45°C. Nachdem keine pH-Änderung mehr zu beobachten ist, erhöht man auf 50°C, fügt 10 g Filterhilfe und 5 g Aktivkohle zu und klärt die Lösung ab. Zum warmen Filtrat fügt man 30 g Kochsalz und rührt so lange, bis Raumtemperatur erreicht ist. Der gelbe Reaktivfarbstoff wird abgesaugt und bei 70°C getrocknet. Man erhält 120 g eines salzhaltigen Farbstoffpulvers, das Baumwolle in brillantem, grünstichig gelben Ton färbt und dem nachstehende Struktur zukommt (λmax (H₂O)=423 nm).The moist yellow paste is stirred in 400 ml of water and dissolved with lithium hydroxide solution at pH 6.5. 44 g of freshly sublimed 2,3-dichloro-6-quinoxalinecarboxylic acid chloride are added to the solution, which has been heated to 45 ° C. The acylation reaction is now kept constant between 6.5 and 7.0 by metering in soda solution. The temperature is still 45 ° C. After no further change in pH can be observed, increase to 50 ° C., add 10 g of filter aid and 5 g of activated carbon and clarify the solution. 30 g of table salt are added to the warm filtrate and the mixture is stirred until room temperature is reached. The yellow reactive dye is filtered off and dried at 70 ° C. This gives 120 g of a salt-containing dye powder which dyes cotton in a brilliant, greenish yellow tone and has the structure below (λ max (H₂O) = 423 nm).
Ersetzt man nun in Beispiel 1 die Kupplungskomponente 3-Aminocarbonyl-1,4-dimethyl- 5-sulfomethyl-6-hydroxy-2-pyridon durch vergleichbare Pyridonderivate, so gelangt man zu ebenfalls wertvollen Farbstoffen, die Baumwolle alle in der gleichen grünstichig gelben Nuance färben.If, in example 1, the coupling component 3-aminocarbonyl-1,4-dimethyl 5-sulfomethyl-6-hydroxy-2-pyridone by comparable pyridone derivatives, see above you also get valuable dyes, the cotton all in the same Color greenish yellow shade.
Claims (7)
R₂ = CH₂SO₃H, SO₃H,
R₃ = H, CH₃ oder C₂H₅.3. Dyes according to claim 1 of the following formula in which
R₂ = CH₂SO₃H, SO₃H,
R₃ = H, CH₃ or C₂H₅.
R₃ = H, CH₃ oder C₂H₅.5. Dyes according to claim 1 of the following formula in which
R₃ = H, CH₃ or C₂H₅.
- a) Aminoazofarbstoffe der Struktur (5),
wobei
R₁, R₂ und R₃ die anfangs genannte Bedeutung haben,
mit 2,3-Dichlor-6-(bzw. 5-)chinoxalincarbonsäurechlorid in Gegenwart säurebindender Mittel kondensiert, oder aber - b) das Monokondensationsprodukt aus 2,4-Diaminobenzolsulfonsäure
und 2,3-Dichlor-6-(bzw. 5-)chinoxalincarbonsäurechlorid in üblicher
Weise diazotiert und auf sulfato- oder sulfogruppenhaltige Pyridone
der Struktur (6) oder solche der Struktur (7),
wobei
R₁, R₂ und R₃ die anfangs genannte Bedeutung zukommt,
kuppelt.
- a) aminoazo dyes of structure (5), in which
R₁, R₂ and R₃ have the meaning given above,
condensed with 2,3-dichloro-6- (or. 5-) quinoxaline carboxylic acid chloride in the presence of acid-binding agents, or else - b) the monocondensation product of 2,4-diaminobenzenesulfonic acid and 2,3-dichloro-6- (or. 5) quinoxalinecarboxylic acid chloride is diazotized in a conventional manner and on pyridones of structure (6) or those of structure (7) containing sulfato or sulfo groups, in which
R₁, R₂ and R₃ have the meaning given above,
couples.
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19904032923 DE4032923A1 (en) | 1990-10-17 | 1990-10-17 | New reactive sulpho:phenyl:azo-pyridone dyes |
EP91109244A EP0465829B1 (en) | 1990-06-19 | 1991-06-06 | Reactive azodyes |
DE59104208T DE59104208D1 (en) | 1990-06-19 | 1991-06-06 | Azoreactive dyes. |
US07/712,860 US5212289A (en) | 1990-06-19 | 1991-06-10 | Reactive azo dyestuffs obtained by coupling diazotized acylamino-aminobenzene sulfonic acid compounds with pyridone derivatives |
JP3167427A JPH07122029B2 (en) | 1990-06-19 | 1991-06-13 | Reactive azo dye |
BR919102506A BR9102506A (en) | 1990-06-19 | 1991-06-18 | DYES, PROCESS FOR PREPARING COMPOUNDS AND PROCESS FOR DYING OR PRINTING A FIBROUS MATERIAL |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19904032923 DE4032923A1 (en) | 1990-10-17 | 1990-10-17 | New reactive sulpho:phenyl:azo-pyridone dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
DE4032923A1 true DE4032923A1 (en) | 1992-04-23 |
Family
ID=6416452
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19904032923 Withdrawn DE4032923A1 (en) | 1990-06-19 | 1990-10-17 | New reactive sulpho:phenyl:azo-pyridone dyes |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE4032923A1 (en) |
-
1990
- 1990-10-17 DE DE19904032923 patent/DE4032923A1/en not_active Withdrawn
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