DE2159305A1 - Water-insoluble monoazo dyes and process for their preparation - Google Patents

Description

■ "ί

PATENT LAWYERS DR.-ING. H. FINCKE DIPL.-ΙΝΘ. H. BOHi: - P-IMG 3.STÄEGE !? 3 0 NOV

MONKS 5 MOLLERSTR. 31

Imperial Chemical Industries Limited, London, Great Britain

Water-insoluble monoazo dyes and methods too

their manufacture

The invention relates to water-insoluble monoazo dyes,

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which are used for the coloring of textiles from aromatic Polyesters are suitable.

According to the invention, water-insoluble monoazo dyes of the formula

ir - (ί bV ν

(CH ₂ ) COHH ₂

created*

wherein X, Y and Z each represent a hydrogen atom, a chlorine atom, a bromine atom or a cyano, nitro, trifluoromethyl, lower alkylsulfonyl, carbo-lower alkoxy, Represent lower alkyl hydrocarbon or benzoyl group *

η and m represent 1, 2 or 3, respectively, and the bensol ring B, if necessary, by a lower alkyl » or lower alkoxy group, a chlorine or bromine atom or an acylamino group of the formula -NHCOW, wherein W is Represents lower alkyl radical, can be substituted ο

Preferably η and m each represent 2 «

For the purposes of the invention, the terms “lower alkyl” and “lower alkoxy” are intended to include alkyl _and alcohol groups

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to be understood as having 1 to 4 carbon atoms »

As examples of Niederalky! Sulfonyl »,

and lower alkyl hydrocarbon radicals X, Y m & Z kaan

one methylsulfonyl, ethylsulfonyl, Carboethoxy and acetyl radicals

Metbyl, A'tfayl, Methosey, Stoxy and Kropo radicals may be mentioned as examples of the lower alkyl and lower alkoxy radicals that may be present on the B ring. As examples of the acylamino radical formula -NHCOW which may be present on BenzolriEg B, propionylamino radicals and radicals can be mentioned _o

According to another feature of the invention Mii? D a Process for the preparation of the dyes described proposed »which consists in the fact that an amine of the formula

T -

diazotized and the resulting diazo compound with a coupling component of the formula

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is coupled, which is in the para position to substituted amino group, where X, Γ, Z, B, η and m have the meanings given.

The method according to the invention can be expedient thereby realize that sodium nitrite becomes a solution or suspension of the amine in a optionally aqueous organic acid is added, and that the resulting solution or suspension the diazo compound to a solution or suspension the coupling component in water, which may optionally be an inorganic acid or a water-soluble one contains organic liquid is added o Han can then, if desired, adjust the pH value of the Adjust the resulting mixture to facilitate the coupling, whereupon the dye obtained is isolated by customary methods.

The following can be mentioned as examples of these amines: aniline, 2- or 4-nitroaniline, 2,4 - dinitraniline, 2,4-, 6-trinitraniline, 2-chloro, 2-bromo or 2-cyano-4-nitroaniline, 2,4-dinitro-6-chloro-, -bromo- or -cyan-aniline, 2,6-Diehlor- or 2,6-

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Dibromo-4-nitr aniline, 2,4 ~ 0icyananiline, 2-carbomethoxy-, 2-acetyl- or 2-methylsulfonyl-4-nitroaniline, 2-trifluoromethylaniline and 2-bromo-6-chloro-4-nitroanilino

These coupling components can be prepared in that the corresponding amine of the formula

reacted with a cyanoalkyl halide in the presence of calcium carbonate, the resulting cyanoalkyl radical to the carbonamide alkyl radical by treatment hydrolyzed with sulfuric acid and the compound obtained with a cyanoalkyl halide in counter waiting for calcium carbonate to condense. The preferred coupling components are those at where m and η each mean 2 «. These can be produced by using the said amine condensed with a wood component acrylonitrile, the cyano group hydrolyzed to a carbonamide group and the compound obtained is further condensed with acrylonitrile, but it is also possible that To condense amine with a molar proportion of acrylic acid amide and then condense the product with acrylonitrile.

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The following can be mentioned as examples of the coupling components mentioned: N- (β-carbonamidethyl) -N- (β-cyanoethyl) aniline, 2 _f 5 = dimethoxy-N- (β-carbonamidethyl) -N- (β-cyanoethyl) aniline , 3-acetylamino, 3 _»f methyl 3-chloro- or 3-bromo-N- (ß-carbonamidäthyl) -N- (beta-cyanoethyl) aniline and 3-acetylamino-6-methoxy-N or metfayl- - (ß-carbonamidätbyl) -N- (ß-cyanoethyl) -aniline ,

The monoazo dyes according to the invention are suitable for dyeing textiles made from aromatic polyesters, in particular from polyethylene terephthalate » Such fabrics can take the form of threads, yarns, Twisted or knitted or woven fabrics have »The dyes can be applied to textile fabrics made from aromatic polyesters by dyeing, padding or printing processes in accordance with the methods customary for applying dispersion aso dyes to such fabrics to be applied "

The dyes according to the invention have an excellent affinity for aromatic textile fabrics Polyesters so that deep shades can be achieved »The colorations obtained are yellow to blue and have excellent fastness to wet treatments, light and dry heat treatments ο

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The dyes according to the invention are also suitable for dyeing synthetic linear polyesters in der Hasse, whereby they are incorporated into the finished polyester For this purpose, the dye can be used in the form of a powder or as a dispersion in a liquid medium, ζ "Β", water or ethylene glycol. «In the latter case, the polyester is dried before extrusion to remove the liquid» Shavings from the polyester can be melted and extruded into threads or other molded parts in conventional systems _{0 However} , the dye is preferably added to the polyester melt shortly before it is extruded into threads or other molded parts the dye used completely or too is at least essentially free of inorganic salts, dispersants or other additives, such as those normally found in technical disperse dyes o The dye is also added to the polyester melt as a melt or preferably as tablets or granules, the addition being made by precise metering in order to ensure this , that

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the dye is evenly distributed in the polyester, what is essential for a uniform coloring of the extruded polyester

The invention is explained in more detail below with the aid of examples purely by way of example, wherein the specified parts and percentages by weight are absorbed

example 1

2.0? Parts of 2,6-dichloro-4-nitroaniline are added within 30 Hinuten to a solution of nitrosyl sulfuric acid at 25 ° C, which was prepared by dissolving 0.7 parts Hatriumnitrit in 5 parts of sulfuric acid The mixture is ο 1 hour at 25 ⁰ C. stirred "the solution of the diazo compound thus obtained is supplied at 5 ⁰ C a solution of 2.17 parts of N- (beta-Carbonamidäthyl) -N- (beta-cyanoethyl) aniline in 100 parts of an aqueous O, 2n-Salzsäurelöeung, and The mixture is stirred for 30 minutes at 5 ^° C. The precipitated dye is filtered off, washed with water and dried, _etc.

When dyeing textiles made of polyethylene terephthalate from an aqueous dispersion of this dye, the dye produces yellow-brown shades that have excellent fastness to light and wet treatments ο q

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Example 2

Polyethylene terephthalate in chip form comes with processed into threads in a screw extruder, wherein the dyestuff according to Example 1 as granules to the extruder via a suitable feed device is fed continuously, in such a way that 1 part of dye to 100 parts of the through the extruder guided polymer is added o

The threads are thereby evenly dyed in a yellow-brown shade of excellent fastness properties

Further examples are given in the table below for the dyes according to the invention with the formula

N - N - (/ BV N

indicated, whereby the symbols have the meanings given in the relevant columns of the table » These dyes can be produced by adding the corresponding AmIn of the formula

- 10 -

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diazotized and the intermediate product formed with the corresponding coupling component of the formula

is coupled, analogous to the procedure according to Example 1 »

The last column of the table shows the color tones on textiles made of aromatic polyester _o

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Tabel

Example X

5 6

It bromine η η It bromine η Cyan Il Nitro It It Nitro η chlorine Il chlorine It η Cyan Nitro η hydrogen bromine η η Methylsulfonyl Nitro η η chlorine Il η η Cyan hydrogen it It chlorine π η η It η If It η It η η Methylsulfonyl It Nitro η It Il η It η η

η η η η η

hue

Hydrogen hydrogen hydrogen hydrogen hydrogen 2

2 2 Yellow Red η It orange Blue red η η scarlet It π . η Brown scarlet Il η Il It η η Blue red Blue red η It It Brown η It It
NJ η η 159305
S. η π η η It η η η η η 1 η 2 V) I.

example Table (continued)

hue

19th chlorine bromine bromine π η 20th π Trifluoro
sMthyl Nitro It 21st Carbomethozy
Acetyl hydrogen 22nd Benxoyl π
η 20982 23
24 Carboethoxy
bromine η 25th chlorine It
Nitro 1082 26th
27 It bromine 28 η 29 30th

Nitro

Il

it η

methyl

chlorine

Acety! Amino Hydrogen 2

η η

ti

Brown

"Blue violet

hydrogen π It It Scarlet fever
Red I.
ϊυ
ι η η N Il η π η η η η η
methyl Il
methyl η
It η
It η
It Acetylamino Methoxy It η Navy blue hydrogen methyl It η Brown Il chlorine ti π η η bromine η It Il

CO CjJ O

Claims (2)

Patents a ρ rüche 1. Water-insoluble monoazo dyes of the formula wherein X, T and Z each represent a hydrogen atom, a chlorine atom, a bromine atom or a cyano *, nitro-, triflvormethyl-, Lower alkyl sulfonyl- »carbo-lower alkoxy * -) Represent a lower alkyl hydrocarbon or bensoyl group " η and ■ each represent 1, 2 or 3, and the bensol ring B may optionally be substituted by a lower alkyl or Hlederalkozygruppe, a chlorine or bromine atom or an acylamino group of the formula -HHCOU ₁ wherein V is a _{lower alkyl radical, o} 2. Method of dyes of textile fabrics from aromatic Polyesters, characterized in that a dye according to Claim 1 is applied to the textile material is applied by a paint, pad or printing process. PATENT LAWYERS DHNQ.H.FINaCE.DIPl.-iNS.H.SO.! * DIPL-ING-S-STAEGtK 209824/1082