DE1544451C3 - Water-insoluble monoazo dyes and process for their preparation - Google Patents
Water-insoluble monoazo dyes and process for their preparationInfo
- Publication number
- DE1544451C3 DE1544451C3 DE19651544451 DE1544451A DE1544451C3 DE 1544451 C3 DE1544451 C3 DE 1544451C3 DE 19651544451 DE19651544451 DE 19651544451 DE 1544451 A DE1544451 A DE 1544451A DE 1544451 C3 DE1544451 C3 DE 1544451C3
- Authority
- DE
- Germany
- Prior art keywords
- cyanoethyl
- water
- dyes
- methyl
- mol
- 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
- 239000000975 dye Substances 0.000 title claims description 19
- 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 4
- 238000000034 method Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 description 10
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 230000001808 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 6
- 229940018167 2-amino-5-nitrothiazole Drugs 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- CGPPWNTVTNCHDO-UHFFFAOYSA-N 2-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Br CGPPWNTVTNCHDO-UHFFFAOYSA-N 0.000 description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229960000583 Acetic Acid Drugs 0.000 description 3
- VQTGUFBGYOIUFS-UHFFFAOYSA-N Nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- NOHOYGXEORYNFY-UHFFFAOYSA-N 3-(3-phenylpropoxy)aniline Chemical compound NC1=CC=CC(OCCCC=2C=CC=CC=2)=C1 NOHOYGXEORYNFY-UHFFFAOYSA-N 0.000 description 1
- XDTMMCQOYPEAJM-UHFFFAOYSA-N 3-chloro-N-(2-phenylethyl)aniline Chemical compound ClC1=CC=CC(NCCC=2C=CC=CC=2)=C1 XDTMMCQOYPEAJM-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- KHAYUQIOYHYRCC-UHFFFAOYSA-N 3-methyl-N-(2-phenylethyl)aniline Chemical compound CC1=CC=CC(NCCC=2C=CC=CC=2)=C1 KHAYUQIOYHYRCC-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N M-Anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Description
CH2CH2 CH 2 CH 2
CH7CH7CNCH 7 CH 7 CN
worin der Phenylkern K noch in 5-Stellung, in 6-Stellung und in 2-Stellung zur Aminogruppe wie vorstehend angegeben substituiert sein kann, kuppelt.wherein the phenyl nucleus K is still in the 5-position, in 6-position and in 2-position to the amino group may be substituted as indicated above, couples.
O7NO 7 N
2525th
ist und der Phenylkern K noch in 2-Stellung zur Azobrücke durch Chlor, Methyl, Methoxy oder Acetylamino und im Falle von in 2-Stellung zur Azobrücke vorhandenem Methyl oder Acetylamino zusätzlich noch durch Methoxy in 5-Stellung zur Azogruppe sowie im Falle von in 2-Stellung zur Azogruppe vorhandenem Methyl zusätzlich noch durch Chlor in 3-Stellung zur Azogruppe substituiert sein kann.and the phenyl nucleus K is still in the 2-position to the azo bridge by chlorine, methyl, methoxy or Acetylamino and in the case of methyl or acetylamino present in the 2-position to the azo bridge additionally by methoxy in the 5-position to the azo group and in the case of methyl present in the 2-position to the azo group can additionally be substituted by chlorine in the 3-position to the azo group.
2. Verfahren zur Herstellung wasserunlöslicher Monoazofarbstoffe gemäß Anspruch 1 der allgemeinen Formel2. Process for the preparation of water-insoluble monoazo dyes according to claim 1 of the general formula
Die vorliegende Erfindung betrifft wertvolle wasserunlösliche Monoazofarbstoffe der allgemeinen FormelThe present invention relates to valuable water-insoluble monoazo dyes of the general formula
R-N =R-N =
worin R der Restwhere R is the remainder
CH7CH,CH 7 CH,
CH2CH2CNCH 2 CH 2 CN
oderor
R-N =R-N =
worin R der Restwhere R is the remainder
CH2CH2 CH 2 CH 2
CH7CH7CNCH 7 CH 7 CN
O7NO 7 N
O7NO 7 N
=/= /
O7NO 7 N
ist und der Phenylkern K noch in 2-Stellung zur Azobrücke durch Chlor, Methyl, Methoxy oder Acetylamino und im Falle von in 2-Stellung zur Azobrücke vorhandenem Methyl oder Acetylamino zusätzlich noch durch Methoxy in 5-Stellung zur Azogruppe sowie im Falle von in 2-Stellung zur Azogruppe vorhandenem Methyl zusätzlich noch durch Chlor in 3-Stellung zur Azogruppe substituiert sein kann.and the phenyl nucleus K is still in the 2-position to the azo bridge through chlorine, methyl, methoxy or acetylamino and additionally in the case of methyl or acetylamino present in the 2-position to the azo bridge nor by methoxy in the 5-position to the azo group and in the case of those present in the 2-position to the azo group Methyl can also be substituted by chlorine in the 3-position to the azo group.
Die erfindungsgemäßen Farbstoffe werden erhalten, indem man 1 Mol der Diazoniumverbindung eines Amins der allgemeinen Formel RNH2, worin R die vorstehend angegebene Bedeutung hat, mit 1 Mol des tertiären Amins der FormelThe dyes according to the invention are obtained by adding 1 mol of the diazonium compound of an amine of the general formula RNH 2 , in which R has the meaning given above, to 1 mol of the tertiary amine of the formula
ist und der Phenylkern K. noch in 2-Stellung zur Azobrücke durch Chlor, Methyl, Methoxy oder Acetylamino und im Falle von in 5-Stellung zur Aminogruppe vorhandenem Methyl oder Acetylamino zusätzlich noch durch Methoxy in 2-Stellung zur Aminogruppe sowie im Falle von in 5-Stellung zur Aminogruppe vorhandenem Methyl zusätzlich noch durch Chlor in 6-Stellung zur Aminogruppe substituiert sein kann, dadurch gekennzeichnet, daß man 1 Mol der Diazoniumverbindung eines Amins der allgemeinen Formelis and the phenyl nucleus K. is still in the 2-position to the azo bridge by chlorine, methyl, methoxy or Acetylamino and in the case of methyl or acetylamino present in the 5-position to the amino group additionally by methoxy in the 2-position to the amino group and in the case of in 5-position to the amino group additionally still by chlorine in 6-position to the Amino group can be substituted, characterized in that 1 mol of the diazonium compound of an amine of the general formula
5555
60 CH2CH2 60 CH 2 CH 2
CH2CH2CNCH 2 CH 2 CN
worin der Phenolkern K noch in 5-Stellung zur Aminogruppe durch Chlor, Methyl, Methoxy oder Acetylamino und im Falle von in 5-Stellung zur Aminogruppe vorhandenem Methyl oder Acetylamino zusätzlich noch durch Methoxy in 2-Stellungwherein the phenol nucleus K is still in the 5-position to the amino group by chlorine, methyl, methoxy or Acetylamino and in the case of methyl or acetylamino present in the 5-position to the amino group additionally by methoxy in the 2-position
zur Aminogruppe sowie im Falle von in 5-Stellung zur Aminogruppe vorhandenem Methyl zusätzlich noch durch Chlor in 6-Stellung zur Aminogruppe substituiert sein kann, kuppelt.to the amino group and in the case of methyl present in the 5-position to the amino group in addition can still be substituted by chlorine in the 6-position to the amino group, couples.
Die erfindungsgemäßen Farbstoffe eignen sich zum Färben und Bedrucken von Textilmaterialien auf Basis von Celluloseestern, synthetischen Polyamiden und Polyacrylnitril und liefern hierbei Färbungen und Drucke, die sich durch gute Echtheitseigenschaften auszeichnen. Eine besonders hohe Affinität besitzen die beanspruchten Farbstoffe zu Materialien aus aromatischen Polyestern, wie z. B. Polyäthylenterephthalat, die von ihnen mit großer Ergiebigkeit gefärbt werden, wobei Färbungen von sehr guter Sublimier- und Lichtechtheit entstehen. Im Hinblick auf diese Eigenschaften sind die erfindungsgemäßen Farbstoffe den aus der DT-AS 11 64 972 bekannten Farbstoffen wesentlich überlegen. Unter den erfindungsgemäß herstellbaren Farbstoffen haben sich diejenigen als besonders wertvoll erwiesen, die als Diazokomponente 2-Amino-5-nitro-thiazol enthalten. Diese Farbstoffe zeichnen sich insbesondere durch eine hohe Ergiebigkeit aus. Als Kupplungskomponenten können z. B. eingesetzt werden:The dyes according to the invention are suitable for dyeing and printing textile materials Based on cellulose esters, synthetic polyamides and polyacrylonitrile and provide coloration and prints that are characterized by good fastness properties. Have a particularly high affinity the claimed dyes to materials made of aromatic polyesters, such as. B. polyethylene terephthalate, which are stained by them with great yield, staining of very good Sublimation and lightfastness arise. In view of these properties are those according to the invention Dyes are significantly superior to the dyes known from DT-AS 11 64 972. Among the inventively Preparable dyes have proven to be particularly valuable as Diazo component contain 2-amino-5-nitro-thiazole. These dyes are particularly distinguished by a high yield. As coupling components, for. B. can be used:
DiazokomponenteDiazo component
Kupplungskomponente FarbtonCoupling component color
N-ß-Cyanäthyl-N-/?'
N-jS-Cyanäthyl-N-/?'·
N-^-Cyanäthyl-N-^'
N-iS-Cyanäthyl-N-/?'
N-jS-Cyanäthyl-N-/?'·N-ß-cyanoethyl-N- /? '
N-jS-cyanoethyl-N - /? '·
N - ^ - cyanoethyl-N- ^ '
N-iS-cyanoethyl-N- /? '
N-jS-cyanoethyl-N - /? '·
amino)-anilin, ■
N-^-Cyanäthyl-N-/?'amino) aniline, ■
N - ^ - cyanoethyl-N- /? '
5-methyl)-anilin,
N-ß-Cyanäthyl-N-ß'5-methyl) aniline,
N-ß-cyanoethyl-N-ß '
3-methyl)-anilin.3-methyl) aniline.
-phenäthylanilin,-phenethylaniline,
•phenäthyl-m-toluidin,• phenethyl-m-toluidine,
■phenäthyl-m-anisidin,■ phenethyl-m-anisidine,
■phenäthyl-m-chloranilin,■ phenethyl-m-chloroaniline,
■phenäthyl-(m-acetyl-■ phenethyl- (m-acetyl-
■phenäthyl-(2-methoxy-■phenäthyl-(2-chlor- ■ phenethyl- (2-methoxy- ■ phenethyl- (2-chloro-
a) 72,5 g (0,5 Mol) 2-Amino-5-nitro-thiazol werdena) 72.5 g (0.5 mol) of 2-amino-5-nitro-thiazole are
in einer Mischung von 0,5 Mol Nitrosylschwefelsäure und 750 ecm Eisessig-Propionsäure (85 :15) bei 0 bis 5° C diazotiert. Nach 4 Stunden wird die überschüssige Nitrosylschwefelsäure mit etwa 7,5 g Harnstoff zerstört. in a mixture of 0.5 mol of nitrosylsulfuric acid and 750 ecm of glacial acetic propionic acid (85:15) at 0 to 5 ° C diazotized. After 4 hours, the excess nitrosylsulfuric acid is destroyed with about 7.5 g of urea.
b) 125 g (0,5 Mol) N-zJ-Cyanäthyl-N-zf-phenäthylanilin werden in 500 ml Eisessig-Propionsäure (85 :15) gelöst und bei 5 bis 10° C mit der Diazolösung a) versetzt. Nach Zugabe von 250 g Natriumacetat (wasserfrei) wird einige Stunden bei etwa 5° C gerührt. Ist die Kupplung beendet, dann wird der Farbstoff mit 1,5 1 Eiswasser gefällt, abgesaugt und mehrmals mit Wasser gewaschen. Ausbeute: 170g blauschwarzes Farbstoffpulver, das Polyesterfasern in blauvioletten Tönen von sehr guter Licht- und Sublimierechtheit und mit hoher Ergiebigkeit färbt.b) 125 g (0.5 mol) of N-zI-cyanoethyl-N-zf-phenethylaniline are dissolved in 500 ml of glacial acetic acid propionic acid (85:15) and the diazo solution a) is added at 5 to 10 ° C. After adding 250 g of sodium acetate (anhydrous), the mixture is stirred at about 5 ° C. for a few hours. is the coupling is ended, then the dye is precipitated with 1.5 l of ice water, filtered off with suction and repeated several times Water washed. Yield: 170 g of blue-black dye powder, the polyester fibers in blue-violet Shades of very good lightfastness and sublimation fastness and dyes with high yield.
Der vorstehend beschriebene Farbstoff kann auch durch Kupplung in Eisessig Schwefelsäure und Ausfällung mit Eis hergestellt werden.The dye described above can also be obtained by coupling in glacial acetic acid sulfuric acid and precipitation can be made with ice.
In vorstehend beschriebener Weise wurden folgende weitere Farbstoffe hergestellt:The following additional dyes were produced in the manner described above:
DiazokomponenteDiazo component
Kupplungskomponente FarbtonCoupling component color
2-Amino-5-nitrothiazol 2-amino-5-nitrothiazole
N-/?-Cyanäthyl-N-ß'-phenäthylm-toluidin N - /? - cyanoethyl-N-ß'-phenethylm-toluidine
violettviolet
2-Amino-5-nitrothiazol 2-amino-5-nitrothiazole
2-Amino-5-nitrothiazol 2-amino-5-nitrothiazole
2-Amino-5-nitrothiazol 2-amino-5-nitrothiazole
!5 2-Amino-5-nitro-. thiazol! 5 2-amino-5-nitro-. thiazole
N-ß-Cyanäthyl- violettN-ß-cyanoethyl violet
N-/?'-phenäthyl-N - /? '- phenethyl-
m-anisidinm-anisidine
N-ß-Cyanäthyl- violettN-ß-cyanoethyl violet
N-/?'-phenäthyl-N - /? '- phenethyl-
m-chloranilinm-chloroaniline
N-ß-Cyanäthyl- ' blauN-ß-cyanoethyl- 'blue
N-ß'-phenäthyl-N-ß'-phenethyl-
(m-acetylamino)-(m-acetylamino) -
anilinaniline
N-ß-Cyanäthyl- blauN-ß-cyanoethyl blue
N-/?'-phenäthyl-N - /? '- phenethyl-
(o-methoxy-m-ace-(o-methoxy-m-ace-
tylamino)-anilintylamino) aniline
B ei s ρ i e 1 2B ei s ρ i e 1 2
108,5 g (0,5 Mol) 2-Brom-4-nitranilin werden wie üblich diazotiert und zu einer kalten Lösung von 125 g (0,5MoI) N-/S-Cyanäthyl-N-/S'-phenäthylanilin in Aceton gegeben. Man fügt dann solange Natriumacetat zu, bis die Mineralsäure abgestumpft und die Fällung beendet ist. Der so erhaltene Farbstoff wird wie üblich isoliert.108.5 g (0.5 mol) of 2-bromo-4-nitroaniline are diazotized as usual and a cold solution of 125 g (0.5 mol) of N- / S-cyanoethyl-N- / S'-phenethylaniline given in acetone. Sodium acetate is then added until the mineral acid is blunted and the Precipitation is finished. The dye thus obtained is isolated as usual.
Ausbeute: 255 g rotes Farbstoffpulver, das PoIyesterfasern in scharlachfarbenen Tönen von sehr guter Licht- und Sublimierechtheit färbt.Yield: 255 g of red dye powder, the polyester fibers dyes in scarlet shades of very good lightfastness and sublimation fastness.
Der vorstehend beschriebene Farbstoff kann auchThe dye described above can also
durch Diazotierung des 2-Brom-4-nitranilins mit Nitrosylschwefelsäure, Kupplung in Schwefelsäure/ Eisessig und Ausfällung mit Eis hergestellt werden.by diazotizing 2-bromo-4-nitroaniline with nitrosylsulfuric acid, coupling in sulfuric acid / Glacial acetic acid and precipitation can be made with ice.
217 g (1 Mol) 2-Brom-4-nitranilin werden mit 300 ecm konzentrierter Salzsäure und 600 ecm Wasser angerührt und nach Zugabe von 400 g Eis mit einer Lösung von 69 g (1 Mol) Natriumnitrit in 200 ecm Wasser bei 0 bis 5° C vorsichtig versetzt. Nach etwa 1I2 bis 1 Stunde ist die Diazotierung beendet.217 g (1 mol) of 2-bromo-4-nitroaniline are mixed with 300 ecm of concentrated hydrochloric acid and 600 ecm of water and, after addition of 400 g of ice, with a solution of 69 g (1 mol) of sodium nitrite in 200 ecm of water at 0 to 5 ° C carefully shifted. The diazotization is complete after about 1 1/2 to 1 hour.
250 g (1 Mol) N-/3-Cyanäthyl-N-/9'-phenäthylanilin werden in einem Gemisch aus 200 ecm konzentrierter Salzsäure und 800 ecm "Wasser gegebenenfalls unter Zugabe eines handelsüblichen Netzmittels dispergiert und bei 0 bis 5° C mit der in Absatz 1 beschriebenen Diazolösung versetzt. Der ausgeschiedene Azofarbstoff wird in üblicher Weise isoliert.250 g (1 mol) of N- / 3-cyanoethyl-N- / 9'-phenethylaniline are in a mixture of 200 ecm of concentrated hydrochloric acid and 800 ecm "of water if necessary under Addition of a commercially available wetting agent and dispersed at 0 to 5 ° C with that described in paragraph 1 Diazo solution added. The precipitated azo dye is isolated in the usual way.
Man erhält so einen Dispersionsfarbstoff, der Polyesterfasern in scharlachfarbenen Tönen von sehr guter Licht- und Sublimierechtheit färbt.A disperse dye is obtained in this way, the polyester fibers in scarlet shades of very colors with good lightfastness and sublimation fastness.
Nach den in den Beispielen 2 und 3 beschriebenen Methoden wurden folgende weitere Azofarbstoffe hergestellt:The following additional azo dyes were produced by the methods described in Examples 2 and 3 manufactured:
DiazokomponenteDiazo component
Kupplungskomponente FarbtonCoupling component color
2-Brom-4-nitranilin2-bromo-4-nitroaniline
2-Brom-4-nitranilin2-bromo-4-nitroaniline
N-ß-Cyanäthyl- rotN-ß-cyanoethyl red
N-/T-phenäthyl-N- / T-phenethyl-
m-toluidinm-toluidine
N-ß-Cyanäthyl- rubinN-ß-cyanoethyl ruby
N-/?'-phenäthyl-N - /? '- phenethyl-
(m-acetylamino)-(m-acetylamino) -
anilinaniline
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0037232 | 1965-10-23 | ||
| DEC0037232 | 1965-10-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1544451A1 DE1544451A1 (en) | 1969-05-14 |
| DE1544451B2 DE1544451B2 (en) | 1976-01-15 |
| DE1544451C3 true DE1544451C3 (en) | 1976-08-19 |
Family
ID=
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