KR20030024825A - A method for the treatment of textile materials against fungi and dust mites - Google Patents

Abstract

Textile materials for improving antifungal and / or anti-dust mites, comprising the compound of formula 1 in a padding, spraying or foam application or during the dry cleaning process. Methods of treating and similar methods of treating polyacrylonitrile fibers in the gel state are described.

Formula 1

Description

A method for the treatment of textile materials against fungi and dust mites}

The present invention relates to a method of treating textile materials to improve antifungal and / or antidust mites by applying selected specific antifungal agents or antidust mites to the textile material by a specific application method.

Textile products that are antifungal to consumers, particularly textile products that are anti-dust mites, are very appealing. In some respects this characteristic is particularly important. For example, various studies have shown that the human foot is often infected with fungi and causes a variety of diseases, such as Athelet's foot. Thus, when an antifungal textile material is introduced as a member for manufacturing shoes, it may be advantageous to the consumer. In the home textiles sector, dust mites present in the matrix and pillow covers are associated with increased allergy and asthma outbreaks. Since the survival of dust mites depends on the presence of fungal species that metabolize skin flakes and provide vitamin B as a necessary food source for dust mites, suppressing fungi helps to inhibit dust mite growth and thus It is advantageous to the consumer.

In view of the above, there is a need to find a suitable method that can improve these properties and provide long-lasting antifungal activity and antidust mite activity that is durable against repeated washing.

The present invention focuses on providing antifungal efficacy and antidust mite efficacy using specific agents in the desired textile product. Surprisingly, by introducing selected antifungal substances into various substrates made of natural and synthetic fibers, long-lasting antifungal activity that is durable against repeated laundry, dry cleaning, weathering and / or other aging processes And anti-dust mites have been found. Treatment of the textile product with selected formulations and / or formulations containing the formulations can be used in various methods such as padding, spraying and foam coating, as well as in the process of treating polyacrylonitrile fibers in gel form with the formulation. It turns out that you can.

Accordingly, the present invention relates to the treatment of textile materials to improve antifungal and / or dust mite properties, comprising applying the compound of formula 1 to padding, spraying or foam coating or to the textile material during a dry cleaning process. It is about a method.

The compound of formula 1 may be applied as an aqueous formulation in dilute, solubilized, emulsified or preferably dispersed form.

Thus, the aqueous formulations may further comprise small amounts of organic solvents, surfactants, dispersants and / or emulsifiers. These components are useful for solubilizing and stabilizing the compound of formula 1 in an aqueous formulation.

When the compound of formula 1 is applied in dispersed form, it is usually ground with a suitable dispersant using quartz balls and impellers, for example, with a particle size of 0.1 to 4 μm, in particular 0.3 to 3 μm. It is preferable to

Suitable dispersants for the compounds of formula 1

Salts of acid esters or alkylene oxide adducts thereof, typically acid esters or salts of heavy adducts of 4 to 40 mol of ethylene oxide with 1 mol of phenol, or 6 to 30 mol of ethylene oxide and 1 mol of 4-nonylphenol Salts of phosphorylated heavy adducts with 1 mol of dinonylphenol, or 1 mol of a compound prepared by adding 1-3 mol of saturated or unsaturated styrene to 1 mol of phenol,

Polystyrene sulfonates,

Fatty acid taurides,

Alkylated diphenyl oxide mono- or disulfonates,

Sulfonates of polycarboxylates,

1 to 60 mol of ethylene oxide and / or propylene oxide with fatty amines, fatty acids or fatty alcohols, each containing 8 to 22 carbons in the alkyl chain, alkylphenols or carbon atoms containing 4 to 16 carbons in the alkyl chain Heavy adducts with trivalent to hexavalent alkanols of 3 to 6 (where the heavy adducts are converted to acid esters with organic dicarboxylic acids or inorganic polyvalent basic acids),

Ligninsulfonate and, most preferably,

Formaldehyde condensates, for example ligninsulfonates and / or condensates of phenols and formaldehydes, condensates of formaldehyde with aromatic sulfonic acids, typically condensates of dioctyl ether sulfonates with formaldehyde, naphthalene Condensates of sulfonic acids and / or naphthol- or naphthylaminesulfonic acids with formaldehyde, phenolsulfonic acids and / or sulfonated dihydroxydiphenylsulfones and phenols or cresols with formaldehyde and / or ureas and Condensate of diphenyl oxide-disulfonic acid derivatives with formaldehyde.

Preferably, the compound of formula 1 is a condensate of ligninsulfonate and / or phenol and formaldehyde, a condensate of formaldehyde with aromatic sulfonic acid, naphthalenesulfonic acid and / or naphthol- or naphthylaminesulfonic acid and formaldehyde Condensates with phenolsulfonic acids and / or sulfonated dihydroxydiphenylsulfones and phenols or cresols with formaldehyde and / or ureas and with condensates of diphenyl oxide-disulfonic acid derivatives with formaldehyde Dispersed by one or more dispersants selected from the group consisting of: Very preferred are condensates of naphthalenesulfonic acid and / or naphthol- or naphthylaminesulfonic acid with formaldehyde.

Suitable solubilizers are anionic, nonionic or zwitterionic and amphoteric synthetic surfactants.

Suitable anionic surfactants are

Sulfates, fatty alcohol sulfates typically containing 8 to 18 carbons in the alkyl chain, for example sulfated lauryl alcohol,

Fatty alcohol ether sulfates, typically acid esters or salts of polyadditions of from 2 to 30 mol of ethylene oxide with 1 mol of C ₈ -C ₂₂ fatty alcohol,

Alkali metal salts, ammonium salts or amine salts of C ₈ -C ₂₀ fatty acids, typically coconut fatty acids, referred to as soap,

Alkylamide sulfates,

Alkylamine sulfates, typically monoethanolamine lauryl sulfate,

Alkylamide ether sulfates,

Alkylaryl polyether sulfates,

Monoglyceride sulfate,

Alkanesulfonates containing 8 to 20 carbons in the alkyl chain, for example dodecyl sulfonate,

Alkylamide sulfonates,

Alkylaryl sulfonates,

α-olefin sulfonates,

Sulfosuccinic acid derivatives, typically alkyl sulfosuccinates, alkyl ether sulfosuccinates or alkyl sulfosuccinamide derivatives,

N- [alkylamidoalkyl] amino acids of formula (2) or

Alkylaryl ether carboxylates or alkyl ether carboxylates of the formula (3).

In Formula 2 above,

X is hydrogen, C ₁ -C ₄ alkyl or -COO ^- M ⁺ ,

Y is hydrogen or C ₁ -C ₄ alkyl,

Z is (Wherein m ₁ is 1 to 5),

n is an integer from 6 to 18,

M is an alkali metal ion or an amine ion.

CH ₃ -XYA

In Formula 3 above,

X is , or Is a radical of wherein R is hydrogen or C ₁ -C ₄ alkyl,

Y is ego,

A is or (Wherein m ₂ is 1 to 6 and M is an alkali metal cation or an amine cation).

In addition, the anionic surfactants used may be fatty acid methyl taudes, alkylisothionates, fatty acid polypeptide condensates and fatty alcohol phosphate esters. The alkyl radicals in these compounds preferably contain 8 to 24 carbons.

Anionic surfactants are generally obtained in the form of their water soluble salts, for example alkali metal, ammonium or amine salts. Typical examples of such salts are lithium, sodium, potassium, ammonium, triethylamine, ethanolamine, diethanolamine or triethanolamine salts. Sodium salt, potassium salt or ammonium- (NR ₁ R ₂ R ₃ ) salts wherein R ₁ , R ₂ and R ₃ are each independently of one another hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ hydroxyalkyl Is preferably used.

Suitable zwitterionic and amphoteric surfactants include imidazoline carboxylates, alkyl ampocarboxy carboxylic acids, alkyl ampocarboxylic acids (eg lauroampoglycinate) and N-alkyl-b-aminopropionates or N -Alkyl-b-iminodipropionate.

Nonionic surfactants are typically derivatives of adducts of propylene oxide / ethylene oxide with molecular weights of 1000 to 15000, fatty alcohol ethoxylates (1-50 EO), alkylphenol polyglycol ethers (1-50 EO), ethoxylation Carbohydrates, fatty acid glycol partial esters, typically diethylene glycol monostearate, PEG 5 glyceryl stearate; PEG 15 glyceryl stearate; PEG 25 glyceryl stearate; Cetearyl octanoate; Fatty acid alkanolamides and fatty acid dialkanolamides, fatty acid alkanolamide ethoxylates and fatty acid amine oxides.

In addition, saturated and unsaturated C ₈ -C ₂₂ fatty acid salts can be used as solubilizers by themselves, in admixture with one another or in admixture with other surfactants. Examples of these fatty acids are typically capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid, dodekenic acid, tetradekenic acid, octadekenic acid, oleic acid, eicosanic acid and As well as luc acid. Industrial mixtures of these acids, typically coconut fatty acids. These acids can be obtained in salt form, suitable cations are alkali metal cations such as sodium and potassium cations, metal atoms such as zinc atoms and aluminum atoms or nitrogen containing organic compounds with sufficient alkalinity, Typically may be amines and ethoxylated amines. These salts can also be prepared in situ.

In addition, suitable solubilizers are dihydric alcohols, preferably those containing 2 to 6 carbon atoms in the alkylene radical, typically ethylene glycol, 1,2- or 1,3-propanediol, 1,3-, 1 , 4- or 2,3-butanediol, 1,5-pentanediol and 1,6-hexanediol, monohydric alcohols such as methanol, ethanol and propanol, and acetone.

In such aqueous formulations, in particular dispersions, the concentration of the compound of formula 1 is generally from 0.001 to 30% by weight, in particular from 0.1 to 20% by weight, based on the weight of the formulation. The concentration of the compound of formula 1 is very preferably 0.1 to 10% by weight, in particular 1 to 5% by weight.

The amount of additionally added components, for example dispersants or surfactants, is preferably from 0.1 to 30% by weight, in particular from 1 to 20% by weight, based on the weight of the aqueous formulation.

Aqueous formulations, in particular dispersions prepared by the above methods, can be diluted in almost any ratio.

For all of the applications below, it is preferred to add the compound of formula 1 in the form of the aqueous formulation, in particular dispersion.

Padding may be performed according to a conventional padding method. For example, the fabric material is passed through an aqueous liquor containing the compound of formula 1 and the fabric material is woven at a defined liquor pick-up rate, followed by a fixing step, preferably a heat treatment.

The amount of the compound of formula 1 in the aqueous liquor (padding liquor) is generally from 0.001 to 10% by weight, in particular from 0.01 to 10% by weight, based on the weight of the aqueous liquor. The amount of the compound of formula 1 is preferably 0.01 to 5% by weight.

The liquor pick up ratio is generally from 40 to 200% by weight, in particular from 50 to 150% by weight, based on the weight of the fabric material.

Generally, the fixing step is carried out by heat treatment at a temperature of, for example, 60 to 150 ° C, in particular 90 to 150 ° C.

Padding is generally carried out in a continuous process, where the fabric material is passed continuously through an aqueous liquor containing the compound of formula (1).

According to a preferred method, the compound of formula 1 is applied to the fabric material by padding, wherein the fabric material is via an aqueous liquor containing 0.001 to 10% by weight of the compound of formula 1, based on the weight of the aqueous liquor. Pass it continuously.

Spraying can be carried out according to conventional spraying methods. According to this method, an aqueous liquid containing the compound of formula 1 is sprayed onto the fabric material. The amount of the compound of formula 1 in the aqueous liquor is generally from 0.001 to 10% by weight, in particular from 0.01 to 10% by weight, based on the weight of the aqueous liquor. The amount of the compound of formula 1 is preferably 0.1 to 10% by weight. The spraying method is particularly suitable for applying the compound of formula 1 to textile materials such as carpets. According to this preferred method, a plurality of spray nozzles are arranged, for example, on a spray line perpendicular to the direction of movement of the carpet. The compound of formula 1 is applied as an aqueous liquor with a spray nozzle, for example using pressure.

After spraying, a fixing step is generally carried out, which can be carried out by heat treatment as described above for the padding method.

The spraying method can also be used to apply the compound of formula 1 in the form of an aqueous liquor to the surface of a textile material, including leather such as sofas or shoes.

According to another preferred method, the compound of formula 1 is applied to the fabric material by spraying, wherein an aqueous liquor containing 0.001 to 10% by weight of the compound of formula 1 is sprayed onto the fabric material, based on the weight of the aqueous liquor. do.

In addition, the compound of formula 1 may be applied to the fabric material by a foam coating method. For this method, all the conditions and preferences described above for the spraying method apply. However, the compounds of formula (1) are generally applied in the form of aqueous foams which further contain foam stabilizers. The method is also particularly suitable for carpet treatment.

According to a further preferred method, the compound of formula 1 is applied to the textile material by foam coating method, wherein it contains from 0.001 to 10% by weight of the compound of formula 1 and optionally a foam stabilizer, based on the weight of the aqueous foam An aqueous foam is applied to the fabric material.

Padding, spraying or foaming application can be carried out by applying the compound of formula 1 to the textile material together with the dye (eg in a dyeing process) or in other textile related processes such as finishing processes. Preference is given to treating with the compound of formula 1 in the presence of a dye.

If the process is carried out in the absence of dyes, it is preferred to apply the compound of formula 1 in the finishing process.

The use of some polymeric and oligomeric materials commonly used in the textile industry can help to further enhance the durability of the desired antifungal and anti-dust mite efficacy. Such materials include resin pinning agents, softening agents, coatings, fixatives and / or other finishing agents, such as hydrophilic and lipophilic agents, flame retardants, and the like, which provide easy protection and / or other properties to various textile materials. However, this is not limiting. In view of economics and ease of processing, antimicrobial treatment can be performed in conjunction with a number of other different types of treatments used in the textile industry.

In addition, the application of the compound of formula 1 may be carried out in a dyeing process, which is carried out by a padding method, spraying method or foam coating method. For these methods, the above conditions and preferences apply. Suitable dyes are disperse dyes, basic dyes, acid dyes, direct dyes or reactive dyes. Reactive dyes are particularly suitable for natural polyamide- or cellulose containing textile materials. Direct dyes are particularly suitable for cellulose containing textile materials. Dyes belong to a variety of dye classes, including acridon, azo, anthraquinone, coumarin, formazan, methine, perinone, naphthoquinone-imine, quinophthalone, styryl or nitro dyes. Mixtures of dyes may also be used.

When the compound of formula 1 is used in a dyeing process, the process first treats the fabric material with the compound of formula 1 and then dyes, or preferably the fabric material is treated simultaneously with the compound of formula 1 and a dye. . However, the dyeing process may be performed first, and then the compound of formula 1 may be applied.

The treatment liquid may also contain additional components such as dyeing aids, dispersants, carriers, wool protectants and wetting agents as well as defoamers.

The treatment liquid is also a mineral acid, typically sulfuric acid or phosphoric acid or is typically an organic acid, typically containing an aliphatic carboxylic acid such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or May contain sodium acetate. Acids are used in particular to adjust the pH of the liquor, for example to 3-6.

After carrying out the dye process comprising the compound of formula 1, a fixing step such as heat treatment as described above on the fabric material can be performed.

In addition to the above application process, it is also possible to apply the compound of formula 1 in the presence or absence of a dye according to the usual exhaustion process.

In addition, the compound of formula 1 may be applied during the dry cleaning process. Depending on the dry cleaning process, organic solvents, in particular volatile organic solvents such as perchloroethylene or trichloroethylene, are typically used as cleaning medium. Typical dry cleaning processes consist of washing, cleaning and drying cycles. Preference is given to using organic solvents containing from 0.001 to 10% by weight of the compound of formula 1, based on the weight of the organic solvent. Regarding the amount of the compound of formula 1, the preferences as described above for the padding method apply.

According to a preferred embodiment, the compound of formula 1 is applied to the fabric material during a dry cleaning process, wherein the fabric material comprises from 0.001 to 10% by weight of an organic solvent, based on the weight of the organic solvent, It is preferably treated with perchloroethylene or trichloroethylene.

Textile materials that can be treated with the compound of formula 1 include, for example, natural or synthetic polyamides (eg, wool, silk and nylon), polyurethanes, polyesters, polypropylene, polyethylene, polyacrylonitrile and Cellulose-containing textile materials of all kinds, including, for example, natural cellulose fibers (eg, cotton, linen, jute and hemp) and viscose staple fibers and regenerated cellulose; Or blends of such fiber materials, for example polyacrylonitrile / polyester, polyamide / polyester, polyester / cotton, polyester / viscose and polyester / wool.

Preferred textile materials are wool, synthetic polyamides, polyesters, polypropylene, polyethylene and cellulose containing textile materials, preferably cotton or wool, especially those comprising cotton.

The fabric material may be provided in different forms, as a woven, knitted or piece good, such as a knitted product, nonwoven, carpet, yarn or staple fiber. Nonwoven materials, in particular carpet, are preferred.

A number of end use products are named for products made from treated fabrics or treated materials. For example, carpets and rags, pillow covers, bed linings, bed sheets, matrices and matrix tickings, curtains, duvet and duvet covers, uphostery, socks and apparel Include, but are not limited to.

Further, the present invention relates to a method for treating polyacrylonitrile fibers for improving antifungal and / or anti-dust mite, comprising coating a compound of formula 1 in a polyacrylonitrile fiber in a gel state. .

Formula 1

The gel state of the polyacrylonitrile fiber is understood as the expanded state immediately after the preparation of the fiber (the fiber just spun; typically after bulk removal of the non-aqueous spinning solvent used to make the fiber). This is described in US Pat. No. 4,563,191.

Such treatment can be carried out according to conventional methods. For example, polyacrylonitrile fibers are treated in an aqueous liquor containing 0.001 to 10% by weight, in particular 0.01 to 5% by weight, based on the weight of the aqueous liquor. The amount of the compound of formula 1 is preferably 0.01 to 1% by weight. Preferably, the treatment is carried out at a temperature of 20 to 100 ° C, in particular 40 to 80 ° C. The pH of the aqueous liquor is preferably 3-6 for the treatment. If desired, the fibers may be compressed after treatment so that the pick-up ratio of the particular liquid is, for example, from 50 to 300%, in particular from 100 to 300%. The heat treatment can then be carried out, for example, to dry the treated fibers at a temperature of from 60 to 200 ° C, in particular from 90 to 200 ° C.

In addition, the above treatment can be carried out during the dyeing process of the fibers. In this case, the conventional dyeing method of dyeing the fiber in a gel state is applied. Dyes to be used include basic dyes. In this way, dye is present in the aqueous liquor used in the treatment.

In addition, treatments using the compound of Formula 1 may be performed with other chemical agents that provide a variety of benefits to the fiber to provide a variety of functions. Preference is given to using antimicrobial agents together with antimicrobial substances which exhibit good activity in inhibiting the growth of bacteria, including gram positive and gram negative bacteria, in the presence of a compound of formula (1).

In all the application methods of the compound of the formula (1) described above, a method for improving antifungal properties is preferred. Similarly, a method for improving anti-dust mites is desirable. Very preferred are methods for improving antifungal and antidust mites.

In the examples below, the percentages are by weight.

Example 1: Preparation of Formulation 1

Tolnaftat [2-naphthyl-N-methyl-N- (3-tolyl) thionocarbamate, Cas No. 2398-96-1) 35 g, 105 g naphthalenesulfonic acid / formaldehyde condensation product and 560 ml of water are mixed. The mixture is then homogenized for 24 hours with a tumbling machine. The silica sand is then filtered off and the resulting formulation 1 contains 5% tolnaftat. The median particle size of tolnaftat in this formulation is measured at about 2 μm and the specific surface area is 3.73 m ² / g.

(Molecular structure of tolnafart)

Example 2: Introduction of Formulation 1

10 g of formulation 1 is added to 500 ml of water. The fabric made of 100% cotton fibers was impregnated in the bath and then with a Lab Padding Machine (Mathias) so that the liquid pickup ratio was 80% owf (on the weight fabric). Squeeze. The fabric obtained is then dried at 120 ° C. for 5 minutes in a fan assisted oven.

Example 3: Introduction of Formulation 1

10 g of Formulation 1 is added to 450 ml of water with 40 g of Dilanlan AS (product capable of forming a thin film on the fabric, Ciba Specialty Chemicals Inc., Switzerland). . The knitted fabric made of 100% cotton fiber is impregnated in the bath and then pressed with a wrap padding machine (Matthias) so that the liquid pickup ratio is 80% o.w.f. The resulting fabric is then dried at 120 ° C. for 5 minutes in a fan mounted oven.

Example 4: Introduction of Formulation 1

10 g of formulation 1 is added to 500 ml of water. The fabric made of 100% wool fibers is impregnated in the bath and then pressed with a wrap padding machine (Matthias) so that the liquid pickup ratio is 80% o.w.f. The fabric obtained is then dried at 120 ° C. for 5 minutes in a fan mounted oven.

Example 5 Introduction of Formulation 1

Formulation 1 is diluted with water in a ratio of 1: 1 (weight / weight). The diluted formulation is then sprayed onto a fabric made of 100% wool fibers at room temperature with an introduction amount of 2% based on the weight of the fabric. The treated fabric is dried at 70 ° C. for 10 minutes in an oven.

Example 6: Preparation of Formulation 2 (Comparative Example)

After dissolving 10 g of 2,4-dichlorobenzyl alcohol in 87 g of 1,2-propylene glycol, 3 g of sodium lauryl sulfate, an anionic surfactant, is added. The formulation obtained is a clear solution. Upon further dilution with water, the formulation becomes a milky dispersion.

Example 7: Introduction of Formulation 2 (Comparative Example)

200 g of Formulation 2 are further diluted with 800 ml of water to prepare a dispersion. Cotton fabrics are padded with the dispersion at a pickup rate of 100%. In addition, the padded fabric is dried at 70 ° C. in a fan mounted oven.

Example 8: Preparation of Formulation 3 (Comparative Example)

10 g of a- (2- (4-chlorophenyl) ethyl) -a- (1,1-dimethylethyl) -1H-1,2,4-triazole-1-ethanol (CAS N0.107534-96-3) Is added to 30 g of 1,2-propylene glycol and 60 g of Marlipol 24/99 (nonionic surfactant). The obtained product is shown as Formula 3.

Example 9 Introduction of Formulation 3 (Comparative Example)

20 g of formulation 3 is added to 1000 ml of water. Knitted fabrics made of 100% cotton fibers are padded with a wrap padding machine (Matthias) such that the liquid pick up ratio is 80-100%. In addition, the padded fabric is dried at 120 ° C. for 5 minutes in a fan mounted oven.

Example 10 Introduction of Formulation 1

In Example 10, the just spun wet (water content about 170%) polyacrylonitrile fiber is treated. Prepare a treatment bath, which consists of the following ingredients:

Formulation 1 50 g

Tinosan AM 100 [antimicrobial agent, manufacturer: Ciba Specialty Chemicals Inc. (Switzerland)] 50 g

Add water to make 1000 ml.

The pH of the treatment bath is adjusted to 4.5.

The treated bath is heated to 55-60 ° C. and the wet spun polyacrylonitrile fiber just immersed in the bath and held for about 5 seconds, and then the treated fiber is wrapped so that the total wet pick up ratio is about 200%. Press with a padding machine. The treated wet fibers are then dried at 160 ° C. for 15 minutes in an oven.

Example 11: Washing of Fabrics and Fibers

The treated fabrics and / or fibers are occasionally washed by conventional laundering methods to investigate the wash durability of the antimicrobial and / or anti-dust mite activity provided by various treatments with various formulations. Unless otherwise noted, cleaning conditions are as follows:

Cleaning conditions: according to standard method (BS 4923 4A standard)

Detergent: Persil 2.25% o.w.f.

Washing machine: Wascator FOM 71 MP

Temperature: 50 ± 3 ℃

Cycle time: 50 minutes

Liquer Ratio: 1:10

Rinsing: 4 cycles, room temperature

Agitation: gently

Drying: Tumble Dryer

Samples are washed for various cycles, for example 5, 10 and 20 cycles.

Example 12 Antimicrobial Activity of Fabrics Treated with Formulation 1

(a) Method principle

Punch a fabric disc 2 cm in diameter from the sample. The disc is applied to the top layer of solidified agar containing the fungal suspension (5 ml of washed agar slant is added to 500 ml of molten agar and 5-6 ml is distributed on the bottom layer). Then all plates are left at 28 ° C. After incubation, the inhibition zone around the sample (20 mm disc) is measured, the growth under the disc is evaluated (Vinson rating) and listed in Table 1.

Fungus: Aspergillus niger ATCC 6275

Medium: Sabouraud agar + 4% glucose (two layers of agar: 15 ml bottom layer without bacteria and 6 ml top layer containing fungi)

Incubation: 5 days at 28 ° C

Fabric samples tested Test strain: Aspergillus Niger ATCC 6275 ZI VR Cotton (control) 0/0 0/0 Cotton treated as described in Example 2 5/5 4/4 20 washes of cotton treated as described in Example 2 3/3 4/4 Cotton treated as described in Example 3 5/5 4/4 20 washes of cotton treated as described in Example 3 3/4 4/4 Wool (control) 0/0 0/0 Wool treated as described in Example 4 6/6 4/4 Dry clean three times with a wool washing machine treated as described in Example 4. 3/3 4/4 Wool treated as described in Example 5 6/6 4/4

All tests are performed twice and all two results are listed in the table above.

Legend: ZI = zone of inhibition in mm

VR = Vinson's assessment of growth under the disc

[L.J. Vinson et al., J. Pharm. Sci. 50, 827-830, 1961]

0 = active growth under disc (no activity)

4 = no growth under the disc (good activity)

Example 13: Antimicrobial Activity of Fabrics Treated with Formulation 1

The antimicrobial performance of polyacrylonitrile fibers prepared as described in Example 10 is also evaluated. In addition to fungal strains for testing, representative bacteria (gram positive and gram negative) are also selected. Cultures are performed overnight (18-24 hours) when performing tests involving bacteria. Other test methods are the same as described in Example 12. The results represented by the inhibitory region are shown in Table 2 below.

Samples treated as described in Example 10 Treatment with Formulation 1 and Tino Acid AM 100 Treatment with Formulation 1 Only microbe Suppression Area (mm) Aspergillus Niger ATCC 6275 2/2 2/2 Trichophyton Mentagrophytes ATCC 9533 7/7 5/5 Staphylococcus aureus ATCC 9144 30/30 0/0 Escherichia coli NCTC 8196 20/20 0/0

Example 14 Antimicrobial Activity of Fabrics Treated with Formulation 2 (Comparative Example)

The antimicrobial performance of the sample treated with Formulation 2 is evaluated according to the method described in Example 12. This gives the following results:

Samples treated as described in Example 7 Treated with Formulation 2, not washed Treatment with Formulation 2, 10 washes microbe Suppression Area (mm) Aspergillus Niger ATCC 6275 0/0 0/0 Trichophyton Mentagrophytes ATCC 9533 12/12 0/0 Staphylococcus aureus ATCC 9144 3/3 0/0 Escherichia coli NCTC 8196 7/7 0/0

All tests are performed twice and all two results are listed in the table above.

Example 15 Antimicrobial Activity of Fabrics Treated with Formulation 3 (Comparative Example)

The test is carried out according to the method described in Example 12.

Fabric samples tested (samples treated as described in Example 9) Microorganism: Aspergillus Niger ATCC 6275 Microorganism: Trichophyton mentagrophytes ATCC 9533 ZI VR ZI VR Treated with 10 g / L of Formulation 3, not washed 1/1 4/4 5/5 4/4 Treated with 10 g / L of Formulation 3, 20 washes 0/0 0/0 0/0 0/0 Treated with 20 g / L of Formulation 3, no washing 3/3 4/4 8/8 4/4 20 g / L of Formulation 3, 20 washes 0/0 0/0 0/0 0/0

All tests are performed twice and all two results are listed in the table above.

Claims (16)

A method of treating textile material to enhance antifungal and / or anti-dust mite, comprising applying the compound of formula 1 to padding, spraying or foam application or during the dry cleaning process. . Formula 1 The method of claim 1 wherein the compound of formula 1 is applied to the textile material together with the dye in a dyeing process carried out by padding, spraying or foam coating. The method of claim 1 wherein the compound of formula 1 is applied to the textile material in a finishing process carried out by padding, spraying or foam coating. The method of claim 1, wherein the compound of formula 1 is applied to the textile material as an aqueous formulation in dilution, solubilization, emulsification or dispersion form. 5. The compound of claim 1, wherein the compound of formula 1 is selected from the group consisting of salts of acid esters or alkylene oxide adducts thereof; Polystyrene sulfonate; Fatty acid taurides; Alkylated diphenyl oxide mono- or disulfonates; Sulfonates of polycarboxylates; 1 to 60 moles of ethylene oxide and / or propylene oxide and fatty amines, fatty acids or fatty alcohols (each containing 8 to 22 carbons in the alkyl chain), alkylphenols or 4 to 16 carbons in the alkyl chain Polyadditions with trivalent to hexavalent alkanols of from 6 to 6, wherein the polyaddition is converted to an acid ester with an organic dicarboxylic acid or an inorganic polyvalent basic acid; Dispersing with at least one dispersant selected from the group consisting of ligninsulfonates and formaldehyde condensates. The compound of claim 1, wherein the compound of formula 1 is selected from the group consisting of ligninsulfonate and / or condensates of phenol and formaldehyde; Condensates of formaldehyde with aromatic sulfonic acid; Condensates of naphthalenesulfonic acid and / or naphthol- or naphthylaminesulfonic acid with formaldehyde; One selected from the group consisting of phenolsulfonic acids and / or sulfonated dihydroxydiphenylsulfones and condensates of phenols or cresols with formaldehyde and / or urea and condensates of diphenyl oxide-disulfonic acid derivatives with formaldehyde Method to be dispersed by the above dispersant. The compound of formula 1 according to claim 1, wherein the compound of formula 1 is applied to the fabric material by padding, wherein the fabric material is 0.001 to 10% by weight based on the weight of the aqueous liquor. The process is passed continuously through an aqueous liquor containing the compound of. 7. A compound according to any one of claims 1 to 6, wherein the compound of formula 1 is applied to the textile material by spraying, wherein the compound contains from 0.001 to 10% by weight of the compound of formula 1, based on the weight of the aqueous liquor. A method wherein an aqueous liquor is sprayed onto the fabric material. The compound of any one of claims 1 to 6, wherein the compound of formula 1 is applied to the textile material by foam coating method, wherein the formula is 0.001 to 10% by weight based on the weight of the aqueous foam. An aqueous foam containing the compound of 1 and optionally a foam stabilizer is applied to a textile material. 7. The compound of claim 1, wherein the compound of formula 1 is applied to the fabric material during dry cleaning, wherein the fabric material is 0.001 to 10 weights based on the weight of the organic solvent. Process with organic solvent, preferably perchloroethylene or trichloroethylene, containing% of compound of formula (1). The method of claim 1, wherein the textile material is selected from natural or synthetic polyamides, polyurethanes, polyesters, polypropylenes, polyethylenes, polyacrylonitriles, and cellulose-containing textile materials. The process according to claim 1, wherein the textile material is selected from wool, synthetic polyamide, polyester, polypropylene, polyethylene and cellulose containing textile materials, preferably cotton and wool. The method according to claim 1, wherein the textile material is a nonwoven or a carpet, preferably a carpet. A method of treating polyacrylonitrile fibers for improving antifungal and / or anti-dust mites, comprising coating a compound of formula (1) in a polyacrylonitrile fiber in a gel state. Formula 1 The method of any one of claims 1 to 14 for improving antifungal properties. The method according to any one of claims 1 to 14, for improving anti-dust mites.