DE1444240B - Process for coloring and printing polypropylene fibers - Google Patents

Description

Despite numerous efforts, it has not yet been possible to produce modified and unmodified polypropylene materials fibrous structure in a way that fully satisfies the needs of the practice to be colored or printed. Those previously proposed for dyeing unmodified polypropylene materials Dyes are not satisfactory. About the dyeability of polypropylene fiber materials To improve with dyes, one has gone over to the fiber in a suitable manner modify (see A.J. Hall, Skinner's Silk and Rayon Record, September 1962, pp. 799 to 800).

For dyeing polypropylene fibers that have been modified by metals or metal compounds, it has recently proposed dyes compared to those previously known for dyeing polypropylene Dyes should have improved fastness properties (see Chemical Week, November 24, 1962, p. 65). These dyes also do not yet adequately meet the requirements in practice Dimensions.

It has now been found, surprisingly, that fibers are modified and not modified Polypropyfeiitiniemraener 'way in achieving Dyeing or printing previously unattainable fastness properties! Monoazo dyes of the composition

OH

R - N = N - R ₁

used.

In this formula, R denotes a benzothiazolyl-2 radical optionally substituted in 5 positions by a methoxy group, R ₁ denotes the radical of a pyrazolone coupling component in which the azo group is adjacent to the hydroxyl group; the radical R ₁ can have other customary substituents, such as nitro, cyano, alkyl, alkoxy, optionally substituted amino, acylamino, hydroxy, rhodanic, carboxylic acid, halogen, trifluoroalkyl, sulfonic acid, optionally substituted sulfonamide and carbonamide and carboxylic acid ester groups; however, the dyes should not carry any sulfonic acid groups.

The process is carried out in detail in such a way that the finely dispersed dyes (I) on the polypropylene fibers or fabrics from neutral, acidic or alkaline aqueous suspensions using dispersants or emulsifiers from a dyebath or a padding liquor, preferably at temperatures from 50 to 130 ⁰ C, applies. In the pad-dyeing, it is expedient zwischenzutrocknen and at 70 to 90 ⁰ C then for a short time to heat to 130 ° C. At temperatures of up to 100 ° C., it is generally advantageous to add common carrier substances, such as trichlorobenzene, diphenyl, diphenyl ether or esters of aromatic carboxylic acids, to the dyebath.

Suitable dispersants or emulsifiers, which are advantageously added to the dyes the commercial products, such as sulfite cellulose breakdown products, condensation products from higher Alcohols and ethylene oxide, soaps, polyglycol ethers of fatty acid amides, formaldehyde condensation products aromatic sulfonic acids or mixtures of such compounds.

The dyes, which are sparingly soluble or insoluble in water, can also be printed onto polypropylene fabric be applied. The printing paste can with a common thickener such as methyl cellulose, Locust bean gum, industrial gum or sodium alginate, may be thickened and otherwise the usual additives for printing pastes, such as urea, thiourea or thioglycol, or others Contain additives that are used to apply water-insoluble dyes, such as methylated Alcohols, sodium m-nitrobenzenesulfate or aqueous emulsions of sulfonated oils. The printing paste is expediently applied to the fabric by printing with printing material, spray device, stencil, Sieve or roller applied, after which the printed material is dried and, if desired, steamed at atmospheric pressure

or in a closed vessel at overpressure when a temperature above 100 ° C, e.g. B. between 110 and 130 ° C is required.

Following the dyeing or printing of the polypropylene fibers, the colored materials can be aftertreated in the usual way, for. B. by using a hot aqueous soap solution and / or a solution of a synthetic detergent.

Coupling components of the pyrazolone series are used as coupling components for the synthesis of the dyes (I) called the following: l-PhenyW-methyl-S-pyrazolon, 1 - phenyl - 5 - pyrazolone - 3 - carboxylic acid methyl or ethyl ester, l- (3'-chlorophenyl) -3-methyl-5-pyrazolone and! - ^ ', S'-dichlorophenyO-S-methyl-S-pyrazolone. Of course, in addition to these, a large number of other substitution products of the coupling components can be used can be used, but sulfonic acid groups should not appear as substituents.

The azo dyes used according to the process pull very quickly onto the polypropylene fiber on. The dyeings and prints available have very good fastness properties out. In addition to very good dry cleaning resistance, the excellent ones are particularly noteworthy Rub, wash and light fastness.

Particularly favorable dyeing results are obtained when the methods are to be used Dyes are used for dyeing polypropylene fibers, 'those with nickel, zinc, magnesium, Copper or cobalt in the form of their oxides, fatty acid salts, phenolates, dithiocarbamates, triazoles and the like. have been modified.

Compared to what is known from Belgian patent specification 614566, p. 10, line 5 from below Dyestuff is characterized by the dyestuff of the formula which can be used according to the process

= N- C - C-CH,

in its coloring on nickel-modified polypropylene fiber fabric due to better dry rub fastness out.

example 1
0.2 g of the dye of the composition

N = N-C C-CH,

HO

QH

CH, O

CH,

Dyed at 100 ^° C. for an hour. The somewhat yellowish-orange dyeing obtainable in this way is characterized by very good fastness properties.

Replacing the azo component in the dye of this example with the azo components in the following Table shows that dyes are obtained which are also valuable dyeings on modified polypropylene materials deliver in the specified colors.

H ₅

are in 400 ml of water containing 0.2 g of a conventional dispersant (e.g. a naphthalenesulfonic acid-formaldehyde condensation product) and 0.2 ml of 30% acetic acid, dispersed and added to 10 g of polypropylene fiber yarn for one hour Colored cooking temperature. After a subsequent slightly alkaline aftertreatment at 50 ° C below The addition of 0.5 g / l of a commercially available detergent produces a yellow color with very good wet, rub, Maintain solvent and light fastness.

Instead of the azo dye with l-phenyl-3-methyl-5-pyrazolone you can also use the dyes with 1- (2 ', 5'-dichlorophenyl) -3-methyl-pyrazolon-5 with equally good results or use 1- (3'-chlorophenyl) -3-methylpyrazolon-5.

The metal-modified polypropylene fibers used in this example are those polypropylene fibers which, in addition to UV absorbers and stabilizers, are nickel phenolates from bis (alkylphenol) monosulfides Contained spun.

B e is ρ i e 1 2

100 g of polypropylene fiber material in the form of a sliver are diluted in 2 l of water Sulfuric acid is adjusted to a pH of 4 to 5 and in addition to 4 g of methyl salicylate also 4 g contains a weakly anionic alkylphenyl polyglycol ether sulfate, with 1 g of the finely dispersed Dye of the composition

Azo component Hue of staining
on with metals or
Metal connections
modified
Polypropylene fibers 1 - (3'-chlorphenyl) -3-methyl-
pyrazolone-5
l- (2 ', 5'-dichlorophenyl) -3-methyl-
pyrazolone-5 orange
orange

Claims (3)

Patent claims: 1. A method for dyeing and printing polypropylene fibers, characterized in that that one sulfonic acid group-free monoazo dyes of the formula OH
RN = NR ₁ where R is a benzothiazolyl-2 radical optionally substituted in the 5-position by a methoxy group and R _{1 is} the radical of a pyrazolone coupling component in which the azo group is adjacent to the hydroxyl group. 2. The method according to claim 1, characterized in that the dyes are in the presence of dispersants or emulsifiers from a dye bath or a padding liquor at temperatures from 50 to 130 ° C on the polypropylene fiber. 3. Process according to Claims 1 and 2, characterized in that metals or Metal compounds modified polypropylene fibers are dyed or printed.