DE2229127C3 - Monoazo dye, process for its preparation and its use - Google Patents
Monoazo dye, process for its preparation and its useInfo
- Publication number
- DE2229127C3 DE2229127C3 DE19722229127 DE2229127A DE2229127C3 DE 2229127 C3 DE2229127 C3 DE 2229127C3 DE 19722229127 DE19722229127 DE 19722229127 DE 2229127 A DE2229127 A DE 2229127A DE 2229127 C3 DE2229127 C3 DE 2229127C3
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- monoazo dye
- dye
- dyeing
- acid
- 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.)
- Expired
Links
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 6
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- IRFCTHNJIWUUJZ-UHFFFAOYSA-N n-(3-aminophenyl)benzamide Chemical compound NC1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1 IRFCTHNJIWUUJZ-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 polyethylene Polymers 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002678 cellulose Polymers 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
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 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
Description
ClCl
Ο,Ν—Ο, Ν—
NH,NH,
NHCONHCO
dadurch gekennzeichnet, daß man 2-Chlor-4-nitranilin diazotiert und auf m-Benzoylaminoanilin kuppelt.characterized in that 2-chloro-4-nitroaniline diazotized and coupled to m-benzoylaminoaniline.
3. Verfahren zum Färben und Bedrucken von hydrophoben Fasermaterialien, dadurch gekennzeichnet, daß man den Monoazofarbstoff des Anspruchs 1 verwendet.3. A method for dyeing and printing hydrophobic fiber materials, characterized in that that the monoazo dye of claim 1 is used.
Gegenstand der vorliegenden Erfindung ist der Monoazofarbstoff der FormelThe present invention relates to the monoazo dye of the formula
O, NO, N
V-N=N-V-N = N-
V-NH,V-NH,
NHCONHCO
sowie dessen Herstellung und Verwendung zum Färben von hydrophoben Fasermaterialien.as well as its production and use for dyeing hydrophobic fiber materials.
Der Farbstoff wird erhalten, indem man 2-Chlor-4-nitranilin diazotiert und auf m-Benzoylaminoanilin kuppelt.The dye is obtained by adding 2-chloro-4-nitroaniline diazotized and coupled to m-benzoylaminoaniline.
Die Kupplung erfolgt in an sich bekannter Weise im sauren, wäßrigen oder organisch-wäßrigen Medium, gegebenenfalls in Anwesenheit eines säurebindenden Mittels, vorzugsweise Natriumacetat.The coupling takes place in a manner known per se in an acidic, aqueous or organic-aqueous medium, optionally in the presence of an acid-binding agent, preferably sodium acetate.
Der neue Farbstoff eignet sich zum Färben und Bedrucken von hydrophoben Fasermaterialien, z. B. solchen aus synthetischen Celluloseestern und aromalischen Polyestern, insbesondere solchen aus PoIyäthylenierephthalat. The new dye is suitable for dyeing and printing hydrophobic fiber materials, e.g. B. those made from synthetic cellulose esters and aromatic polyesters, in particular those made from polyethylene nerephthalate.
Die Färbung auf synthetischen Polyesterfasern sind besonders wertvoll, indem sie sich durch gute Allgemeinechtheiten auszeichnen.The colorations on synthetic polyester fibers are particularly valuable because they have good all-round fastness properties distinguish.
Gegenüber den nächstvergleichbaren bekannten Farbstoffen der FR-PS 15 72 585 weist der erfindungsgemäße Farbstoff eine Reihe anwendungstechnischer Vorteile, wie höhere Sublimier- bzw. Lichtechtheit, größere Farbstärke und verbessertes Zieh- und Aufbauvermögen, auf.Compared to the closest comparable known dyes of FR-PS 15 72 585, the inventive Dye has a number of application-related advantages, such as higher sublimation and lightfastness, greater color strength and improved drawing and building power.
a) 17,2 g 2-Chlor-4-nitranilin werden bei 40 bis 50 C in 90 g konzentrierter Schwefelsäure gelöst. Dann wird die Lösung auf 5 C abgekühlt, 17 cm1 Nitrosylschwefelsüure zugegeben (110 cm3 = 42 g Nitrit). 1 Stunde gerühn und auf amidosulfonsäurehaltiges Eiswasser gegossen. Zu dieser Diazollösung werden 21,1 g m-Benzoylaminoanilin in 100 cm3 Methanol gelöst bei 0 bis 5 C zugetropft. Dann wird 2 Stunden nachgerührt und danach mit 30%igcr Natriumacetatlösung auf pH 2,5 gestellt. Nach weiterem zweistündigen Rühren wird abgesaugt und neutral gewaschen. Der so dargestellte Farbstoff stellt in getrockneter Form ein rotes Pulver dar.a) 17.2 g of 2-chloro-4-nitroaniline are dissolved in 90 g of concentrated sulfuric acid at 40 to 50.degree. The solution is then cooled to 5 ° C., 17 cm 1 of nitrosylsulfuric acid are added (110 cm 3 = 42 g of nitrite). Stir for 1 hour and pour onto ice water containing amidosulfonic acid. 21.1 g of m-benzoylaminoaniline, dissolved in 100 cm 3 of methanol, are added dropwise at 0 to 5 ° C. to this diazole solution. The mixture is then stirred for a further 2 hours and then adjusted to pH 2.5 with 30% sodium acetate solution. After stirring for a further two hours, the mixture is filtered off with suction and washed neutral. The dyestuff represented in this way is a red powder in dried form.
b) 0,05 g des gut dispcrgicrten Farbstoffes werden bei 40 bis 50 C in 1 1 Wasser eingetragen, daß außerdem 2 g eines Kondensationsproduktes aromatischer Sulfonsäuren und 5 g eines aromatischen Carbonsäureesters enthält und durch Zugabe von Essigsäure auf einen pH-Wert von 4.5 bis 5 eingestellt ist. In dieses Bad geht man mit 10 g eines Gewebes aus Polyestermaterial. Man erhöht die Temperatur des Färbebades im Verlauf von 20 Minuten auf 85'1C, verweilt 20 Minuten bei dieser Temperatur und bringt die Flotte anschließend zum Kochen. Nach einer Kochdauer von etwa 60 bis 90 Minuten ist der Färbeprozeß beendet. Man erhält eine gelbstichigrote Färbung mit guter Sublimier- und Lichtechtheit.b) 0.05 g of the well dispersed dye are introduced into 1 1 of water at 40 to 50 C, which also contains 2 g of a condensation product of aromatic sulfonic acids and 5 g of an aromatic carboxylic acid ester and, by adding acetic acid, to a pH of 4.5 to 5 is set. In this bath you go with 10 g of a fabric made of polyester material. Increasing the temperature of the dyeing bath in the course of 20 minutes at 85 'C 1, dwells for 20 minutes at this temperature and then brings the liquor for cooking. The dyeing process is ended after a cooking time of about 60 to 90 minutes. A yellowish-tinged red dyeing with good sublimation and lightfastness is obtained.
Claims (2)
1. Monoazofarbstoff der Formel
ClPatent claims:
1. Monoazo dye of the formula
Cl
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722229127 DE2229127C3 (en) | 1972-06-15 | Monoazo dye, process for its preparation and its use | |
| CH853873A CH582733A5 (en) | 1972-06-15 | 1973-06-13 | |
| JP6596573A JPS4952220A (en) | 1972-06-15 | 1973-06-13 | |
| GB2834273A GB1424448A (en) | 1972-06-15 | 1973-06-14 | Dyeing polyester fibres |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722229127 DE2229127C3 (en) | 1972-06-15 | Monoazo dye, process for its preparation and its use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2229127A1 DE2229127A1 (en) | 1974-01-03 |
| DE2229127B2 DE2229127B2 (en) | 1975-11-20 |
| DE2229127C3 true DE2229127C3 (en) | 1976-07-01 |
Family
ID=
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