CH580668A5 - Monoazo dispersion dyes - from 3-cyan 4-methyl 6-hydroxy pyrid-2-one with N-substit. as coupling component - Google Patents

Abstract

This patent of addition relates to the prepn. of azo dyes from coupling component of formula (I) and diazotised amines of formula D-NH2, (in which D is phenyl opt. substd. with 1-3 Cl, Br, NO2, CN, CF3, CH3, OCH3, OC2H5, phenyl, acetyl, benzoyl, methoxy-, ethoxy-, beta-methoxy- ethoxy- or benzoyloxy-carbonyl, methoxy- or ethoxy-carbonyloxy, methoxy- or ethoxy-carbonylamino, acetoxy, propionyloxy, benzoyloxy, N-morpholyl sulphonyl, methyl- or ethyl-sulphonyloxy gpas. or phenylsulphonyloxy bearing phenyl gp. or a thienyl gp. opt. substd. with acetyl).

Description

  

  
 



   It has been found that the compounds of the formula I
EMI1.1
 wherein D one optionally up to three substituents from the group consisting of chlorine, bromine, nitro, cyano. Trifluoromethyl, methyl, methoxy, methoxy, phenyl, acetyl, benzoyl, methoxycarbonyl, ethoxycarbonyl, ss-Methoxyäthoxycarbonyl, benzyloxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, methoxycarbonylamino, Athoxycarbonylamino, acetoxy, propionyl oxy, benzoyloxy, N-Morpholylsulfonyl, Methylsulfonylpxy, Athylsulfonyloxy and phenylsulfonyloxy phenyl radical carrying or a thienyl radical optionally bearing an acetyl group, are excellent disperse dyes.



   The preparation of the compounds of the formula 1 is characterized in that an amine of the formula II
D-NH2 (II) diazotized and with the compound of formula III
EMI1.2


<tb> <SEP>;:; CN0 <SEP> (iii)
<tb> <SEP> J <SEP> 0
<tb> <SEP> OH
<tb> <SEP> CH <SEP> CH,
<tb> couples. <SEP> 2 <SEP> 2
<tb>
The dyes obtained in this way give to fibers or



  Fiber materials made from linear aromatic polyesters, cellulose acetates and synthetic polyamides are very valuable real shades of yellow.



   In the following example, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius.



  example 1
12.7 parts of 2-chloroaniline are mixed with 100 parts of water and 25 parts of 30 percent hydrochloric acid, cooled to 0 ", and a likewise cooled solution of 8 parts of sodium nitrite in 20 parts of water is added over the course of 15 minutes while stirring and the mixture is stirred for a further 30 minutes.



   The excess of nitrous azure is destroyed with amidosulphonic acid, the solution is filtered clear and slowly added to a solution of 26.8 parts of the compound of formula III in 200 parts of dimethylformamide, also cooled to 0 ".



   The deposited dye is filtered off, washed neutral and dried.



   The table below shows further dyes of the formula
EMI1.3
 which are produced according to the invention, indicated.



   Table Ex. A1 A2 A3 A4 A5 Now 2 H -Cl H H H 3 H H -Cl H H 4 -Cl H -Cl H H 5 -Cl -Cl H H H 6 -Cl H H H -Cl
7 -Br H H H H 8 H -Br H H H
9 H H -Br H H
10 -CH3 H H H H 11 H -CH3 H H H
12 H H -CH3 H H
13 -CH3 -Cl H H H
14 -CH3 H -Cl H H
15 H -Cl H H -CH3
16 CH3 H H H -Cl
17 -Cl -CH3 H H H
18 H -CH3 -Cl H H
19 H -CH3 H -Cl H
20 H -CH3 H H -Cl
21 -Cl H -CH3 H H
22 H -Cl -CH3 H H Ex. A1 A2 A3 A4 As
No.



  23 -Br H -CH3 HH 24 H -Br -CH3 HH 25 H -CF3 HHH 26 HH -CF3 HH 27 -CF3 HHHH 28 HHHHH 29 -Cl H -CF3 HH 30 -Cl HH -CF3 H 31 -CH3 H -Br HH 32 -CH3 HH -Br H 33 -OCH3 HHHH 34 H -OCH3 HHH 35 HH -OCH3 HH 36 -OC2Hs HHHH 37 H -OC2H5 HHH 38 HH -OC2H5 HH 39 -C6H5 HHHH 40 H -C6H5 HHH 41 H -C6H5 - COOCH2C6H5 HH 42 H -COOCH2CH2OCH3 HHH 43 -NO2 HHHH 44 H -NO2 HHH 45 HH -NO2 HH 46 -Cl H -NO2 HH 47 -CH3 H -CH3 HH 48 -CH3 HH -CH3 H 49 -CH3 HHH -CH3 50 - CH3 -CH3 HHH 51 H -CH3 -CH3 HH 52 -Br H -Br HH 53 -Cl H -OCH3 HH 54 -Cl HH -OCH3 H 55 H -Cl -OCH3 HH 56 -OCH3 H -Cl HH 57 H -OCH3 -Cl HH 58 H -NHCOOC2H5 HHH 59 HH -COCH3 HH 60 HHHH 61 H -COCH3 HHH 62 H -CN HHH 63 HH -CN HH 64 H -CN -Cl HH 65 HHHH -COOCH3 66 H -COOCH3 HHH 67 HH -COOCH3 HH 68 HHHH

   -COOC2H5 69 H -COOC2H5 HHH 70 HH -COOC2H5 HH 71 -NO2 H -CH3 HH 72 -NO2 H -Cl HH 73 -NO2 H -Br HH 74 H -COOC2H5 -Cl HH 75 HH -COC6Hs HH 76 H -OCOC2Hs HHH 77 HH -OCOC6H5 HH 78 H -OCOC6H5 HHH 79 H -OCOOCH3 HHH 80 H -OCOOC2Hs HHH 81 H -OSO2CH3 HHH 82 H -OSO2C2Hs HHH 83 H -OSO2C6H5 HHH 84 HH -OSO2CH3 HOSH2 HH2H -s HOSH2. H2H -s HOSH2. H2H -s 87 HH -COOC2Hs -COOC2Hs H
EMI3.1


<tb> Example <SEP> 88 <SEP> CH3 <SEP> CN
<tb> <SEP> IICLN <SEP> = <SEP> N <SEP> AO
<tb> <SEP> OH
<tb> <SEP> and <SEP> 0
<tb> <SEP> and <SEP> 2
<tb> <SEP> example <SEP> 89.

   <SEP> CH3CN
<tb> <SEP> H <SEP> 3C <SEP> CO- <SEP> s / <SEP> = <SEP> = <SEP> 239
<tb> <SEP> S
<tb> <SEP> OH
<tb> <SEP> Lso
<tb> <SEP> 2
<tb>

 

Claims (1)

PATENT CLAIM Process for the production of azo compounds of For EMI3.2 in which D one optionally up to three substituents from the group consisting of chlorine, bromine, nitro, cyano, trifluoromethyl, methyl, methoxy, ethoxy, phenyl, acetyl, benzoyl, methoxycarbonyl, ethoxycarbonyl, 13-methoxyethyoxycarbonyl, benzyloxycarbonyl, methoxycarbonyloxy, ethoxycarbonyioxy, methoxycarbonylamino , Acetoxy, propionyloxy, Benzoyloxy, N-morpholylsulfonyl, methylsulfonyloxy, ethylsulfonyloxy and phenylsulfonyloxy-bearing phenyl radical or a thienyl radical optionally bearing an acetyl group, characterized in that, that an amine of the formula II D-NH2 diazotized and with the compound of formula (111) EMI3.3 clutch.