DEF0013022MA - - Google Patents
Info
- Publication number
- DEF0013022MA DEF0013022MA DEF0013022MA DE F0013022M A DEF0013022M A DE F0013022MA DE F0013022M A DEF0013022M A DE F0013022MA
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- diazotized
- acid
- amino
- methyl
- 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.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 12
- ULWHWCKQINGKAY-UHFFFAOYSA-N 2-amino-4-methyl-1,3-thiazole-5-carbonitrile Chemical compound CC=1N=C(N)SC=1C#N ULWHWCKQINGKAY-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229960000583 Acetic Acid Drugs 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000011528 polyamide (building material) Substances 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DELJOESCKJGFML-DUXPYHPUSA-N (E)-3-aminobut-2-enenitrile Chemical compound C\C(N)=C/C#N DELJOESCKJGFML-DUXPYHPUSA-N 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
Tag der Anmeldung: 14. Oktober 1953 Bekanntgemacht am 17. Mai 1956Registration date: October 14, 1953. Advertised on May 17, 1956
DEUTSCHES PATENTAMTGERMAN PATENT OFFICE
Es wurde gefunden, daß man neue wertvolle, wasserunlösliche Monoazofarbstoffe erhält, wenn man diazotiertes 2-Amino-4-methyl-5-cyanthiazol mit kupplungsfähigen Aminobenzolabkömmlingen vereinigt, die keine Sulfonsäure- oder Carbonsäure-It has been found that new valuable, water-insoluble monoazo dyes are obtained if one diazotized 2-amino-4-methyl-5-cyanthiazole with couplable aminobenzene derivatives combined that do not contain sulfonic acid or carboxylic acid
^ gruppen enthalten. Infolge ihrer großen Kupplungsehergie läßt sich diese Diazoverbindung auch mit Verbindungen vereinigen, die üblicherweise nicht zur Herstellung von Azofarbstoffen Verwendung finden.^ groups included. As a result of their great clutch hergy this diazo compound can also be combined with compounds that are customary cannot be used for the production of azo dyes.
Das 2-Amino-4-methyl-5-cyanthiazol läßt sichThe 2-amino-4-methyl-5-cyanthiazole can
nach Bulletin of the Chemical Society of Japan 25 (1952), Nr. i, S. 16 bis 18, aus Diacetonitril durch Bromieren und Umsetzung mit Thioharnstoff herstellen. according to Bulletin of the Chemical Society of Japan 25 (1952), No. i, pp. 16 to 18, from diacetonitrile Brominate and react with thiourea.
Die neuen Farbstoffe eignen sich z. B. zum Färben von Acetatkunstseide, vollsynthetischen Fasern, wie Polyamidfasern, Polyurethanfasern, Polyesterfasern oder Polyacrylnitrilfasern, sowie Lacken und Kunststoffen. Die mit den neuen Farbstoffen erhältlichen Färbungen zeichnen sich durch große Klarheit und gute Lichtechtheit aus. Den aus der deutschen Patentschrift 789 850 bekannten Farbstoffen sind die neuen Farbstoffe in der Lichtechtheit deutlich überlegen.The new dyes are suitable for. B. for dyeing acetate rayon, fully synthetic fibers, such as polyamide fibers, polyurethane fibers, polyester fibers or polyacrylonitrile fibers, as well as paints and plastics. The one with the new dyes available dyeings are characterized by great clarity and good lightfastness. The one from the German Patent 789 850 known dyes are the new dyes in light fastness clearly superior.
zol werden in 50 ecm Schwefelsäure von 400 Be unter starker Kühlung diazotiert. Die intensiv gelbgefärbte Diazolösung läßt man in eine Lösung, hergestellt durch Auflösen von 2/ioo Mol = 3,67 g ι - Dioxäthylamino - 3 - methylbenzol in 25 ecm 5o°/oiger Essigsäure und Austragen auf 1000 ecmzol are diazotized in 50 ecm sulfuric acid of 40 0 Be with strong cooling. The intensive yellow colored diazo solution is allowed in a solution prepared by dissolving 2 / ioo mole = 3.67 g ι - Dioxäthylamino - 3 - methylbenzene in 25 cc 5o ° / discharging cent acetic acid and 1000 cc
609 526/439609 526/439
F 13022 IVb/22 äF 13022 IVb / 22 ä
Eiswasser, einlaufen. Die Kupplung setzt momentan ein. Der Farbstoff wird isoliert, säurefrei gewaschen und getrocknet. Er kann aus Methanol umkristallisiert werden. Er färbt Äcetatkünstseide und Polyamidfasern in klaren violetten Tönen von guter Lichtechtheit.Ice water, run in. The clutch is currently working. The dye is isolated and washed free of acid and dried. It can be recrystallized from methanol. He dyes acetate artificial silk and polyamide fibers in clear violet shades of good lightfastness.
2/ioo Mol = 2,78 g 2-Amino-4-methyl-5-cyanthiazol werden in 50 ecm Schwefelsäure von 400Be bei ο bis 20 diazotiert. Die Diazolösung läßt man in eine Suspension von 2/ioo Mol = 3,26 g i-Diäthylamino - 3 - methylbenzol, hergestellt durch Lösen in 50 ecm Eisessig und Austragen auf 1000 ecm Eiswasser, einlaufen. Die Kupplung setzt momentan ein. Der Farbstoff wird abgesaugt, auf der Nutsche säurefrei gewaschen und getrocknet. Er färbt Acetatkunstseide und Polyamidfasern in klaren violetten Tönen von guter Lichtechtheit. 2 / ioo mole = 2.78 g 2-amino-4-methyl-5-cyanthiazol are diazotized in 50 cc of sulfuric acid of 40 Be at 0 to 2 ο 0th The diazo solution is allowed to a suspension of 2 / ioo mole = 3.26 g i-diethylamino - 3 - methylbenzene, prepared by dissolving in 50 cc of glacial acetic acid, and discharging at 1000 cc of ice-water shrink. The clutch is currently working. The dye is filtered off with suction, washed acid-free on the suction filter and dried. It dyes acetate rayon and polyamide fibers in clear purple tones with good lightfastness.
. . '. . '
2/ioo Mol = 2,78 g
zol werden in 50 ecm Schwefelsäure von 40 ° Be
bei o° diazotiert. Die gelbe Diazolösung läßt man in eine Suspension von 2/ioo Mol = 3,84 g I-Diäthylamino
- 3 - äthoxybenzol, hergestellt durch Lösen in 50 ecm Eisessig und Austragen auf
1000 cm Eiswasser, einlaufen. Der Farbstoff wird isoliert, säurefrei gewaschen und getrocknet. Er
färbt Acetatkunstseide in klären rotvioletten Tönen von guter Lichtechtheit. 2 / ioo mole = 2.78 g
zol are diazotized in 50 ecm sulfuric acid of 40 ° Be at 0 °. The yellow diazo solution is allowed to a suspension of 2 / ioo mole = 3.84 g I-diethylamino - 3 - äthoxybenzol prepared by dissolving in 50 cc of glacial acetic acid, and discharging at 1000 cm of ice-water shrink. The dye is isolated, washed free of acid and dried. He dyes acetate silk in clear red-violet shades of good lightfastness.
Claims (1)
Family
ID=
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