FR2472595A1 - Aq. disperse dye compsn. contg. alkoxylated aryl:phenol - as dispersant, compatible with thickeners, for dyeing and printing synthetic fibres - Google Patents

Abstract

An aq. disperse dye compsn. contains, as dispersant, a non-ionic alkoxylate of an arylphenol. The adduct pref. contains 5-80 (10-30) moles. of alkylene oxide. The alkylene oxide is 2-4C, esp. ethylene oxide. The pref. arylphenols are o-benzylphenol and o- and p-phenylphenol. The compsn. esp. consists of 5-60 wt.% of at least 1 disperse dye, insol. or only slightly sol. in water, 0-50% of a grinding and control agent, 0-90% of water, and 5-90 (10-30)% of the dispersant. The compsn. is used in dyeing and/or printing synthetic fibres. The compsn. is stable and compatible with thickeners, esp. synthetic thickeners used in printing, e.g. derivs. of polyacrylic acid or ethylene-maleic anhydride copolymers. The colour yield is higher. The dye can be fixed at a lower temp., with less migration of the dye particles during heat treatment. Penetration and contrast are improved. Unfixed dye is more rapidly eliminated. There is less staining of other fibres, e.g. cellulosic or animal fibres.

Description

 The present invention relates to aqueous preparations of disperse dyes.

Dispersion dyes used for dyeing and printing synthetic fibers, in particular polyester fibers, are presented in the form of powders or finely dispersed liquids.

The dye preparations presented in liquid form are obtained by grinding, carried out using an appropriate device, in the following manner. The dye resulting from the synthesis is generally mixed and is generally in the form of filter cakes with auxiliary or dispersing and grinding aid products in order to transform the dye, using mechanical energy, into an aqueous dispersion of appropriate finesse and furthermore a level of stability making it possible to satisfy the various requirements of the conditions of application of industrial practice.

 At the end a certain number of compounds of different nature is currently used to carry out the formulation of dispersion dyes.

 Thus, as dispersing agents, which can also possibly serve as regulating agents, various additives are used, in particular anionic compounds, among which there may be mentioned, for example: naphthalene sulfonic acids, naphthalene acids allcylated sulfonic acids, the condensation products of naphthalene or naphtholsulfonic acids or phenol with formaldehyde, polyvinylsulfonates, lignin sulfonic acids, all these different compounds are generally used in the form of alkali metal salts.

 As grinding or regulating agents, mention may be made of hygroscopic substances, protective colloids, dextrin, alginates, cellulose derivatives or polyacrylates.

 The production of these formulations leads to dispersions of dyes in a liquid, stable form, of low viscosity, offering satisfactory results, in the conventional field of dyeing and / or printing of the fibers considered.

More recently, the development in the printing sector of synthetic thickeners, in particular consisting of polyacrylic acid derivatives or ethylene / maleic anhydride copolymers, has made appear a new phenomenon, linked to the nature of these new compounds. .

 It appears in fact that the introduction of the dispersion dyes previously described in a modern printing formula quickly leads to a more or less total liquefaction of the new thickeners thus making it practically impossible to develop these types of products in the presence of dyes. dispersion formulated according to the usual conditions and previously described.

 The present invention aims to overcome these drawbacks by making it possible to prepare aqueous-dispersed dyes having perfect compatibility with the various thickeners and in particular the synthetic thickeners which can be used in the printing sector.

 Thus, the subject of the invention is aqueous preparations of dispersed dyes whose originality consists in that they comprise, as dispersing agent, a nonionic product which is an addition product of an oxide of 'alkylone on an arylphenol.

 According to a preferred embodiment of the invention, the number of moles of alkylene oxide is between 5 and 80 moles and is preferably between 10 and 30 moles.

 This nonionic product is advantageously the addition product of a C2 to C4 alkylene oxide, preferably ethylene oxide, on an aryl phenol chosen from orthobenzylphenol, orthophenylphenol and pa raphenylphenol. .

 The aqueous preparations according to the invention preferably comprise between 5 and 60% by weight of one or more dispersed dyes insoluble or very slightly soluble in water, from 0 to 50% by weight of a grinding agent and of regulation, from 0 to 90% by weight of water, from 5 to 90% by weight, and preferably from 10 to 30%, of the non-ionic dispersing agent.

The dispersed dyes which are insoluble or poorly soluble in water are chosen, for example, from azole, anthraquinone, nitro, methine, quinophthalone, thioxanthenic, diphenylamine, styryl, azostyryl, naphtoperinone or naphthoquinoniminant dyes which do not have hydrosolilising groups in the molecule.

The grinding or regulating agents are chosen from hydrotropic, hygroscopic or regulatory substances such as protective colloids, dextrin, proteins, alginates, gelatin, cellulose derivatives, polyvinylpyrrolidone, polyacrylates, urea and glycol.

The addition of these grinding or regulating agents in the formulation is of course a function of each case; it can, in particular, be omitted.

It has been observed that the preparations of dispersion dyes formulated according to the invention exhibit perfect compatibility with the synthetic thickeners newly introduced in printing, these new preparations not modifying, in particular, the viscosity of the thickeners produced,
The development of these new preparations in the dyeing and / or printing sector has also made it possible to note a certain number of improvements in the dyeing or coloring characteristics compared to the preparations usually formulated and having an anionic character. Applicant has noted in particular that the application of the preparations made according to the invention advantageously allows the following improvements to be made
- higher fixing and yield of dyes, resulting in dyeing and printing, by a gain in dye, or even the possibility of being able to carry out the fixing of the dyestuff, during heat treatments, at your lower rature.

- increased material penetration, resulting in better slicing,
- low migration of dye particles during heat treatments leading to a more regular appearance of the colors produced,
- reduction in soiling of so-called accompanying fibers, for example cellulosic fibers or animal fibers,
- faster elimination of non-fixed dyes, favoring washing operations.

The present invention therefore makes it possible to produce preparations of dispersion dyes which are in a liquid, stable form, of nonionic polarity with a low content of electrolytes and which have no negative influence on the viscosity or the thickening power of synthetic thickeners. such as those for example consisting of polymers or copolymers derived from acrylic acid or ethylene / maleic anhydride copolymers.

The application of the dispersed dye preparations according to the invention leads to a very marked improvement in the color yields.

The anti-migratory effect exerted by the use of these preparations also results in better slicing and better unison of the colors produced.

The present invention will be better understood moreover, and its advantages will emerge clearly from the following examples which illustrate the invention without however limiting it.

Example
The following preparation is first carried out using a rapid mechanical stirrer.

- 30 parts of a filter cake corresponding to the dispersion dye of formula:

- 20 parts of the adduct of 15 moles of ethylene oxide on one mole of o-phenml phenol,
- 50 parts of water.

 The mixture obtained is then ground using a ball mill for 10 hours, the temperature not exceeding 500C.

 After grinding, a finely divided dye is obtained, responding positively to the control tests carried out by filtration and centrifugation, the particle size of which is less than 5 and which appears in the form of a stable, low viscosity liquid.

Applied in dyeing on a polyester fiber according to the conventional process carried out by exhaustion at the temperature of 1300C, the dye allows to obtain an intense blue tone presenting a perfect unison and possessing in addition a high level of solidity.

Example 2
The following mixture is produced using a rapid mechanical stirrer
- 20 parts of a filter cake corresponding to the dispersion dye of formula

- 50 parts of the adduct of 10 moles of ethylene oxide on one mole of o-phenyl phenol,
- 50 parts of water.

 The mixture obtained is ground using a sand mill for 10 h, the temperature not exceeding 500C.

After grinding, a very finely divided dye is obtained, the particle size of which is less than 5 t and which is in the form of a stable liquid of low viscosity.

Applied in dye, on a polyester fiber, according to the conventional process carried out by exhaustion at the temperature of 1300C, the dye allows to obtain an intense blue tone, of excellent leveling with in addition a high level of solidity
Example 3
The following mixture is produced as in the previous examples
- 30 parts of the filter cake corresponding to the dye of formula

30 parts of the adduct of 20 moles of ethylene oxide on one mole of O-benzyl phenol,
- 30 parts of water,
- 10 parts of an aqueous solution of a polyacrylate of soda with a dry matter content of 25 36.

The mixture obtained is ground using a sand mill for 10 hours, the temperature being between 20 and 500C.

 After grinding, a very finely divided dye is obtained, responding positively to the control tests carried out by filtration and centrifugation, the particle size of which is less than 5 μm and which is in a stable, liquid form, of low viscosity. Applied in dye, on a polyester fiber, according to the conventional process carried out by exhaustion, at the temperature of 1300C, the dye allows to obtain an intense red coloring, of a very good leveling and a high level of solidity.

Example 4
A thickener is produced by dispersing 2-parts of a polyacrylic acid of high molecular weight in 100 parts of cold water; after swelling of the product, the pH is adjusted to 8.5 by addition of ammonia.

A thickener is obtained, the viscosity of which, determined using a Brookfield device (speed 10, mobile No. 6), is 52,000 cps.

 A printing color is prepared by mixing with 900 g of this thickener, 100 g of the dye obtained according to the conditions of example No. 1.

After homogenization of the mixture, the determination of the viscosity effected according to the preceding conditions indicates a value of 49,500 cps, that is to say an insignificant modification of the viscosity if account is taken of the dilution effect provided by the dispersion of the dye introduced.

 Carried out under the same conditions, technique and concentration, with an identical dye but previously dispersed with the alkaline salt of a lignosulfonic acid in place of the nonionic compound, the viscosity is 13,000 cps, which corresponds to a very modification important and prohibitive thickening power.

Example 5
A fabric sample consisting of polyester fibers is dyed with the dye obtained according to example 1 and by adopting the following conditions
40 g of the dye obtained in Example 1 are dispersed in one liter of cold water. The pH of the bath is adjusted to the value of 5.5 by addition of acetic acid.

 The fabric sample is then impregnated in this bath by padding, expressed so as to retain only 70% of the impregnation bath, dried at the temperature of 1000C for 2 min then subjected to a heat treatment for 1 minute at the temperature of 220il. The sample is then subjected to rinsing with water and then a reducing alkaline treatment is carried out at a temperature of 600C in order to rid it of all the unbound dye particles.

A sample is obtained which has a particularly intense navy blue color, furthermore demonstrating excellent resistance to tests of resistance to washing, to sublimation or to rubbing.

Carried out under the same conditions with an identical dye but previously formulated with an alkaline salt of a lignosulfonic acid, the sample obtained after dyeing has a less intense coloring than that of the previous sample.

Example 6
A fabric consisting of polyester fibers is dyed with the dye obtained according to example 2. The technical and concentration conditions of Example 5 are adopted.

 After dyeing, an intense blue color is obtained, exhibiting excellent resistance to solidity tests.

Examination of the penetration or slicing obtained on this sample shows excellent penetration of the interior of the tissue with no apparent manifestation of migration of the dye particles to the surface.

 As in the previous example, a sample produced under identical conditions but with a dye having been dispersed with the alkaline salt of a lignosulfonic acid has a 30% lower color intensity. Examination of the slicing of this sample also reveals a low penetration of the fibers with a significant migration of the dye particles on the surface.

Example 7
A fabric sample consisting of a 66/33 mixture of polyester fibers and cellulose fibers is respectively printed with a preparation carried out as follows
100 g of the dispersion dye obtained in Example 1,
- 500 g of an Alginate thickener,
- 400 g of water
After applying the color produced using a flat frame, the sample obtained is dried for two minutes at a temperature of 1000C, then subjected to a 30-minute spray at a temperature of 1300C. The sample obtained is then washed with hot and then cold water.

 We obtain a dark blue color with excellent friction resistance.

 Carried out under the same conditions but with an identical dye having been dispersed with the sodium hydroxide salt of a lignosulfonic acid, the sample has a lower color intensity. It is also observed that this sample has, compared to the previous one, a lower friction resistance, the coloration of the cellulose fiber also appearing to be greater.

Claims (8)

- CLAIMS  1 - PreparatiorEaqueuses disperse dyes, characterized in that they comprise, as dispersing agent, a non-ionic product which is a product of addition of an alkylene oxide on an arylphenol.  2 - Preparations according to claim 1, characterized in that the number of moles of alkylene oxide is between 5 and 80 moles and is preferably between 10 and 30 moles. 3 - Preparations according to claim 2, charac terized in that the nonionic product is the addition product of a C2 to C4 alkylene oxide, preferably ethylene oxide, on a selected aryl phenol among orthobenzylphenol, orthophenylphenol and paraphenylphenol.  4 - Aqueous preparations, characterized in that they contain from 5 to Go% by weight of one or more dispersed dyes insoluble or very slightly soluble in water, from 0 to 50, 'by weight of a grinding agent and regulating, from 0 to 90% by weight of water, from 5 to 90% by weight, and preferably from 10 to 30% of the nonionic dispersing agent, according to any one of claims 1 to 3.  5 - Preparations according to claim 4, characterized in that the dispersed dyes insoluble or poorly soluble in water are chosen from azo, anthraquinone, nitro, methine, quinophthalonic, thioxanthene, biphenylamine, styryl, azostyryl, naphthoquinone or naphthoquinone dyes do not have water-soluble groups in the molecule. 6 - Preparations according to claim 4, characterized in that the grinding or regulating agents are chosen from hydrotropic, hygroscopic or regulatory substances such as dextrin, algi nate, urea, cellulose derivatives, polyacrylates, glycols.  7 - Application of the preparations of the dis persed dyes according to any one of claims 1 to 6, in the printing and / or dyeing of synthetic fibers, characterized in that the said preparations are introduced into the printing paste or the dye bath in the presence of synthetic thickeners sensitive to electrolytes such as polyacrylic acid derivatives or ethylene maleic anhydride copolymers.  8 - Process for dyeing synthetic fibers, characterized in that the fibers impregnated with the preparations of disperse dyes according to any one of claims 1 to 7 are subjected to a heat treatment at a temperature between 130 and 2300C.