DE2951403A1 - Phenyl-azo pyridine dyestuff cpds. esp. useful for polyester - are phenyl-or phenoxy-alkoxy-alkyl hydroxy phenyl-azo methyl cyano pyridone cpds. - Google Patents

Abstract

New pyridone dyestuffs are 1-phenyl- or phenoxy-alkoxyalkyl- 2-hydroxy-3-phenylazo-4-methyl-5- cyanopyrid-6-one cpds. (I) or formula (in which B is -CH2-, -C2H4-, -CHMe-CH2O- or -C2H4O. R is Ph, opt. substd. by 1-4C alkyl or Cl. n is 2 or 3. X is H, Cl, Br, NO2, Me, CF3, Et or carboxylic ester with a 1-8C alcohol component. Y is H, Cl, Me or Et. Z is H, Cl or Me). (I) are prepd. by diazotising (substd.) aniline and coupling with the corresp. pyridone. (I) are specified for dyeing synthetic fibres, esp. polyesters. They give yellow dyeing with high strength and good fastness.

Description

The invention relates to compounds of the general formula I. in the <formula>

l> R phenyl optionally substituted by C1 to C4 alkyl or chlorine, n the numbers 2 or 3, X hydrogen, chlorine, bromine, nitro, methyl, trifluoromethyl, ethyl or carbon ester with 1 to 8 carbon atoms in the alcohol component, Y is hydrogen, chlorine, methyl or ethyl and Z is hydrogen, chlorine or methyl.

Alkyl radicals as substituents for R are propyl, butyl, ethyl and, in particular, methyl.

Alkoxycarbonyl radicals X are, for example: COOCH3, COOC2H5, COOC3H7, COOC4H9, COOC5H11, COOC6H13

To prepare the compounds of the formula I, a diazo compound of amines of the formula II can be used with pyridones of the formula III realize. Details of the preparation can be found in the examples, in which parts and percentages relate to weight, unless otherwise stated.

The compounds of the formula I are yellow and are particularly suitable for dyeing synthetic polyesters. They are distinguished by high color strength and good dyeing fastness properties. Some of them can also be colored with carriers. The bath exhaustion is very good, at the same time the color depth is largely independent of the dyeing temperature in the HT process. Preference is given to dyes of the formula I in which

X methyl, chlorine or nitro, Y hydrogen, methyl or chlorine, Z hydrogen, n is the number 3, B -CH2- or -C2H4O- and R is phenyl or tolyl.

example 1

11 parts of 2-methyl-4-nitro-aniline are stirred with 16 parts by volume of 30% strength hydrochloric acid and 0.3 part of an adduct of 12 moles of ethylene oxide and 1 mole of oleylamine for 1 hour. 80 parts of ice are then added, followed by 14 parts by volume of a 23% strength aqueous sodium nitrite solution, and the diazotization is stirred for 2 hours until it is clear. Excess nitrous acid is then destroyed as usual and the diazonium salt solution is buffered at 0-5 ° C. by adding sodium acetate solution at pH 4.5. 13.1 parts of the pyridone coupling component of the formula are added to the mixture thus obtained which were previously dissolved in 160 parts by volume of water with 4 parts of sodium hydroxide solution (50%), run in within 15 minutes. The coupling is then stirred for 5-7 hours, is then heated to 70 ° C. at pH 4.8 to 5.3 by passing in steam and held at this temperature for 30 minutes. Thereafter, the precipitated dye of the formula

filtered off, washed salt-free with water and dried. 24 parts of a yellow powder are obtained which dyes polyethylene terephthalate fabric in greenish yellow tones which are fast to light and heat-setting.

The high substantivity and the good dyeing properties of the dye when dyeing according to the HAT process at 125 - 135 ° C should be emphasized.

Example 2

5.7 parts of 2-methyl-4-chloro-aniline are stirred with 16 parts of 30% strength hydrochloric acid and 50 parts by volume of water for 30 minutes. The mixture is then cooled to 0 ° C. by adding about 80 parts of ice and 14 parts by volume of an aqueous sodium nitrite solution are then added. The diazotization is stirred at 0 to 5 ° C. for 2 hours. Any excess of nitrous acid is now destroyed with sulfamic acid and the diazonium salt solution is buffered to pH 4.7 by adding sodium acetate. A previously prepared solution of 11.9 parts of the coupling component of the formula is then left

run in 160 parts by volume of water at 25 ° C., 4 parts of 50% strength sodium hydroxide solution and 1 part of an adduct of 30 mol of ethylene oxide with 1 mol of oleyl alcohol within 15 minutes. After stirring overnight, the finished coupling is heated to 70 ° C. at pH 4.8 to 5.5 by running in superheated steam and stirred at this temperature for 1 hour. The easily filterable dye is then filtered off with suction and washed salt-free with water.

After drying, 17.6 parts of a yellow powder of the formula are obtained the polyester fabric dyes in strong yellow tones with good lightfastness. The high substantivity of the dye to the polyester fiber and the favorable dyeing behavior when dyeing on packages at 125 - 135 ° C should be emphasized. The dye melts at 132-135 ° C.

The dyes specified in the tables below are prepared analogously to the procedure described in the examples.

Claims (2)

1. Pyridone dyes of the general formula in the <formula> l> R phenyl optionally substituted by C1 to C4 alkyl or chlorine, n the numbers 2 or 3, X hydrogen, chlorine, bromine, nitro, methyl, trifluoromethyl, ethyl or carbon ester with 1 to 8 carbon atoms in the alcohol component, Y is hydrogen, chlorine, methyl or ethyl and Z is hydrogen, chlorine or methyl. 2. Use of the dyestuffs according to Claim 1 for dyeing synthetic fibers, in particular polyesters.