JPH10183467A - Antimicrobial textile product and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce an antimicrobial textile product, good in operating efficiency when treating the textile product, having excellent antimicrobial properties of the product after treatment, capable of maintaining the antimicrobial properties even by washing many times, hardly causing yellowing or a change in touch feeling of the textile product by the treatment and having high safety and to provide a method for producing the textile product. SOLUTION: Antimicrobial properties are imparted to a textile product by emulsifying, suspending or dissolving α-[2-(4-chlorophenyl)ethyl]-α-(1,1- dimethylethyl)-1H-1,2,4-triazole-1-ethanol (common name: tebuconazole), bringing the textile product into contact with the resultant treating liquid and then carrying out the drying or drying and curing. A binder resin comprising a thermosetting type or a reactive type resin and a catalyst for promoting the curability or reactivity of the resin are especially preferably contained in the treating liquid.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a textile product, and more particularly to a technique for imparting an excellent antibacterial property to the textile product and maintaining the antibacterial property even after a large number of washings. .

[0002]

[Prior art]

<Processing of textiles with disinfectants> Textiles such as underwear, socks, sports clothing, bedding, shoes, etc. are subject to confidential substances and skin exfoliated substances from the user's skin and may be organic substances. Easily contaminated. Since these serve as nutrient sources, they become a medium suitable for bacterial propagation, and as a result, produce unpleasant odors due to bacterial products, and in some cases, cause skin diseases and food poisoning.

[0003] In recent years, hospital-acquired infections due to drug-resistant Staphylococcus aureus have frequently occurred in medical practice, and food poisoning due to pathogenic Escherichia coli O157 has frequently occurred in the food industry, which has become a social problem.

[0004] In view of the above, clothing used in hospitals, nursing clothing, bedding, curtains, rugs, wallpaper, bandages, textiles such as towels, towels, head cloth used in the food industry,
For textile products such as clothes, aprons, towels, and towels, there is a demand for the development of a technique for applying an effective antibacterial treatment to the textile products.

Conventionally, in order to solve such a problem,
A solution containing various disinfectants such as a cationic disinfectant such as benzalkonium chloride and 3- (trimethoxysilyl) propyl octadecyldimethylammonium chloride is adhered to textiles by a method such as dipping, coating, or spraying. That is being done.

[0006] As a method of strengthening the adhesion of a bactericide to a fiber product, for example, a method of binding a part of a bactericidal quaternary ammonium salt to a part of a fiber molecule via an organic silicone compound, a fiber constituent material A method of binding or melting a bactericidal metal compound in the composition to impart antibacterial properties, and a method of retaining the bactericidal compound with an adhesive have also been attempted.

<Protection of Wood and Plastics with Tebuconazole> α- [2- (4-Chlorophenyl) ethyl] -α- (1,1-dimethylethyl) -1H-1,2,4 used in the present invention -Triazole- (1) -ethanol is a kind of 1H triazole-based compound,
It is called tebuconazol by its generic name and is known to have antibacterial and antifungal activity.

For example, JP-A-2-292203 discloses an antibacterial and antifungal (fungicidal and fungicidal) composition comprising a combination of tebuconazole and propiconazole, wherein the composition is a plant or a habitat thereof. It is said to be suitable for processing or preserving wood. According to the examples, this composition is used in the form of a wettable powder, an emulsifiable stock solution, a powder, an extruded granule, a coated granule, and a suspension stock solution. In the upper right column to lower left column on page 2 of this publication,
Regarding tebuconazole, its synthesis method and antibacterial and antifungal activity, EP-A-0040345, EP-A-00524
24.

JP-A-5-132405 discloses a microbicide comprising an azole fungicide such as tebuconazole and an iodopropargyl derivative. It is described that it can be used to protect against microorganisms (wood rot fungi, wood discoloring fungi), and that the form of use can be a solution, suspension, emulsion or paste. This publication states that tebuconazole and propiconazole are used for protection of plants and seeds EP-A-004034.
5, EP-A-0052424.

Japanese Patent Application Laid-Open No. Hei 5-201806 discloses a microbicidal composition comprising an azole derivative (such as tebuconazole) and a benzimidazole derivative. Similarly, JP-A-5-201812 discloses a microbicidal composition comprising an azole derivative (such as tebuconazole) and an iodopropargyl derivative. These compositions are used to protect industrial materials, especially plastics.

JP-A-7-316005 discloses a plant comprising a component I such as tebuconazole and a specific component II.
A microbicidal composition is shown. This composition is said to be capable of suppressing or killing microorganisms generated on plants.

JP-A-8-198711 discloses a wood preservative composition containing a wood preservative represented by a triazole derivative (including tebuconazole) and an inorganic acid as essential components. Dosage forms include wettable powders, emulsions, solubilizers, oils, pastes and the like.

JP-A-8-231313 discloses an industrial antibacterial and antifungal composition containing both tebuconazole and an alkyl 2-benzimidazolylcarbamate as active ingredients. The company says that it will prevent the decline and maintain its appearance. In the examples, the antibacterial and antifungal effects of injection-molded plates after adding this composition (even in the case of 100% tebuconazole) to polypropylene pellets are evaluated.

[0014]

A solution containing a disinfectant such as benzalkonium chloride and 3- (trimethoxysilyl) propyl octadecyldimethylammonium chloride is adhered to textiles by a method such as dipping, coating or spraying. Even if a method such as that described above is adopted, the disinfectant disintegrates without being able to withstand the heating during the processing operation and is reduced in the amount carried, or the processing step becomes complicated and the cost increases. , Falling off due to external influences such as washing, washing, etc., shortening the duration of efficacy, changing the texture of textile products after antibacterial treatment, yellowing over time, product disposal and incineration. There were various disadvantages such as the generation of harmful substances at the time.

On the other hand, triazole derivatives such as tebuconazole are used for protecting plants (wood and the like) and plastics, but only for improving the preservability of the plants and plastics themselves.

The present invention is characterized in that the operability during the treatment of textile products is good, the product after the treatment has excellent antibacterial properties, and the antibacterial properties are maintained even after a large number of washings. It is an object of the present invention to provide an antibacterial fiber product which is unlikely to cause yellowing and hand change of the fiber product and has high safety, and a method for producing the same.

[0017]

According to the present invention, there is provided an antibacterial fiber product comprising α- [2- (4-chlorophenyl) ethyl] -α- (1,1-dimethylethyl) -1H-1,
2,4-triazole- (1) -ethanol (generic name:
Tebuconazole) or a carrier carrying the same and a binder resin.

The method for producing an antibacterial fiber product of the present invention comprises contacting the fiber product with a treatment liquid in which tebuconazole is emulsified, suspended or dissolved in a medium, followed by drying or drying and curing. It is characterized by imparting antibacterial properties to textile products. In this case, it is preferable to use tebuconazole in combination with a binder resin typified by a thermosetting or reactive resin (further, a catalyst that promotes the curability or reactivity of the resin).

[0019]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.

Tebuconazole is conventionally mainly used for plants (especially for wood preservation) as described in the section of the prior art.
And a triazole-based compound having the structure shown in Chemical Formula 1 below.

[0021]

Embedded image

Tebuconazole has an LD ₅₀ of 4000 mg / k
g (rat male, oral administration), extremely low toxicity and no irritation to skin or eyes, so it can be used with confidence even when used in products that come into direct contact with the human body. Also, it has excellent heat resistance, weather resistance and hydrolysis resistance.

The antibacterial fiber product of the present invention comprises:
It carries tebuconazole (or a binder resin).

Examples of fiber products include natural fibers such as cotton, hemp, silk, and wool; regenerated or semi-synthetic fibers such as rayon and acetate; acrylics, polyesters, polyvinyl alcohols, polyamides, polyvinyl chlorides, and polyvinyl chlorides. Examples include products made from synthetic fibers such as vinylidene chloride and polyolefin. The product refers to a yarn, woven fabric, non-woven fabric, knitted fabric, cloth, flocking, cotton-like material, or a product obtained by further cutting, sewing, or secondary processing.

Among these fibers, natural fibers having a reactive functional group, regenerated or semi-synthetic fibers, or some synthetic fibers such as acrylic fibers are preferable because of their high affinity with tebuconazole. However, even if the fibers are polyester-based or polyamide-based fibers, the affinity may be relatively good depending on the physical properties such as the surface state and density of the fibers. Also, for example, an antibacterial fiber product having good washing resistance can be obtained by using a suitable binder resin or a catalyst for the resin even for synthetic fibers having insufficient affinity.

The antibacterial fiber product of the present invention is produced by bringing the fiber product into contact with a treatment liquid in which tebuconazole is emulsified, suspended or dissolved in a medium, and then drying or drying and curing. Thereby, an antibacterial property can be imparted to the fiber product.

Since tebuconazole is a compound that is hardly soluble in water, it is used for treating textile products in the form of a solution in which it is emulsified or suspended or dissolved in a solvent.

The emulsion is obtained by emulsifying a solvent solution of tebuconazole in water with the aid of an emulsifier. As the emulsifier, for example, various surfactants such as sodium polyoxyethylene nonylphenyl ether sulfonate, polyoxyethylene nonylphenyl ether EO (ethylene oxide) adduct, and hydrogenated castor oil EO adduct are used. Examples of the solvent include alcohols (such as isopropanol), glycols (such as butyldiglycol), dimethyl sulfoxide, dimethylformamide, petroleum, alkylbenzene,
Spindle oil, monochloronaphthalene, vegetable oil (castor oil and the like) and the like are used. The emulsion is prepared, for example, by emulsifying an emulsion stock solution having a composition consisting of 5 to 20% by weight of tebuconazole, 5 to 30% by weight of an emulsifier, and 90 to 50% by weight of a solvent in water.

A suspension is obtained by suspending tebuconazole in water with the aid of a dispersing agent. At this time, a thickener may be added, or an antifoaming agent or an antifreezing agent may be added. As the dispersant, for example, various surfactants such as nonylphenol EO phosphate soda salt, styrenated phenol EO phosphate soda salt, lignin sulfonate, and naphthalene sulfonate are used. As the thickener, sodium polyacrylate, xanthan gum and the like are used. The suspension is, for example, 5 to 50% by weight of tebuconazole, 1 to 10% by weight of a dispersant, 0 to 1% by weight of a thickener, 0 to 1% of a cryoprotectant.
It is prepared by diluting a suspension stock solution having a composition consisting of 5% by weight, 0 to 1% by weight of an antifoaming agent and the balance of water with water.

The solvent solution is obtained by dissolving tebuconazole in a solvent. As the solvent, those described above in the description of the emulsion are used. The concentration of tebuconazole in the solution is set, for example, to 0.1 to 30% by weight.

When the fiber product to be treated has insufficient affinity with tebuconazole, or when the affinity is desired to further increase the adhesion, a treatment solution in which tebuconazole is emulsified, suspended or dissolved in a medium. Is preferably made to coexist with a binder resin.

Although a wide range of polymers can be used as the binder resin, it is preferable to use a thermosetting resin or a reactive resin in consideration of adhesion to textiles, prevention of change in hand feeling, operability, and the like. . However, in the case of an emulsion, for example, an acrylic ester emulsion, an aminosilicone emulsion, a urethane elastomer emulsion or the like can be used as the binder resin.

Examples of thermosetting or reactive resins include melamine resins, urea resins, phenol resins, alkyl carbamate resins, glyoxal resins, ketone resins, acetal resins, silicone resins, alkyd resins. It is a condensation reaction type or addition reaction type resin such as a polyester-based resin, an epoxy-based resin, and a urethane-based resin. When used, it is used in the form of an initial condensate, a low-molecular compound, a prepolymer, or the like. Of these, melamine resins, that is, melamine-formaldehyde precondensates or etherified products thereof, especially etherified trimethylolmelamine, are particularly important.

These binder resins are used in the treatment solution
It is desirable to add and use it so that it may be about 0.01% to 5% by weight based on the weight of the fiber product. If the amount of the binder resin is too small, the retention effect of tebuconazole on the textile may not be sufficient,
On the other hand, if the amount is too large, the properties of the fiber product may be impaired, the hand feeling may be deteriorated, and the antibacterial activity of tebuconazole may be rather reduced.

It is also preferable that a catalyst that promotes the curability or reactivity of the resin is present together with a binder resin composed of a thermosetting or reactive resin in the treatment liquid.
Examples of the catalyst include amine catalysts (aliphatic amino alcohol hydrochloride, morpholine hydrochloride, 2-aminobutanol phosphate, etc.), ammonium catalysts (ammonium diphosphate, rhodan ammonium, ammonium chloride, etc.), metal salts Catalysts (magnesium salts, zinc salts, aluminum salts, etc.), free acids and the like, and in particular, amine catalysts and metal salt catalysts are important. Since the amount of the catalyst varies greatly depending on the type of the binder resin, the amount should be an experimentally determined appropriate amount.

In addition, a cross-linking agent that reacts with the functional group of the fiber product may coexist in the treatment liquid. Examples of the crosslinking agent include a phosphorus-containing compound, a polycarboxylic acid, a sulfone compound, a quaternary ammonium salt, 1,3-dichloro-2-propanol, N-methylolacrylamide, ethyleneimine, an alkylketene dimer, and octadecylethylene urea. is there.

In the treatment liquid, if necessary, a plasticizer, a softener, a fluorescent agent, a heat stabilizer, an ultraviolet absorber, a weather resistance improver,
Lubricants, dyes and pigments, antistatic agents, reinforcing agents, flame retardants and the like can also be added. In addition to tebuconazole, other bioactive substances such as insecticides, insect repellents, rat repellents,
A fungicide, a fungicide, and the like can be used in combination to enhance the effect, broaden the antibacterial spectrum, and expand the applicable range.

The contact between the fiber product and the treatment liquid is performed by dipping, coating, spraying or the like. Industrially, a method is used in which a textile is immersed in a treatment liquid at room temperature or heated for a certain period of time, then squeezed, and dried (or dried and cured).

The amount of tebuconazole to be applied is suitably 0.001 to 10% by weight, preferably 0.01 to 5% by weight, based on the weight of the fiber product. When the attached amount of tebuconazole is too small, the antibacterial effect is insufficient.On the other hand, when it is too large, the antibacterial effect is not improved beyond a certain limit.
It is also economically disadvantageous.

<Effect> According to the present invention, tebuconazole is surely supported in a necessary amount even if it is a fiber product made of not only natural fiber but also regenerated or semi-synthetic fiber, furthermore synthetic fiber, or a blend fiber thereof. Can be done.
The treated antibacterial fiber product is highly safe, has excellent antibacterial activity against various bacteria including drug-resistant Staphylococcus aureus and pathogenic Escherichia coli, and its antibacterial properties are not easily impaired even by washing . If you choose the conditions, for example, 10
Antimicrobial activity is maintained even after 0 washes. In addition, the antibacterial fiber product of the present invention hardly causes yellowing or change in feeling even though the antibacterial treatment is performed, has no odor, and does not impair the original taste of the material fiber.

[0041]

Next, the present invention will be described in detail with reference to examples. "CPTE" is tebuconazole. Hereinafter, "%" is% by weight.

<Test Method> The following method was adopted as a test method.・ Washing method: JIS L0217-103 method and JIS L1042: F-2 method +
Add bleach. -Antibacterial test: 2 strains of Staphylococcus au
reus FDA 209P and methicillin-resistant Staphylococcus aureus:
For MRSA) and Escherichia coli (Esherichia coli IFO 3301), the viable cell counts of unprocessed and processed samples were measured by the bacterial count method of the Textile Sanitation Processing Council (SEK). In order to determine the effect, the evaluation index log B / C> 2 was evaluated as valid (○) for simplicity, and the other index was evaluated as no effect (×). Here, B is the viable cell count after culturing the unprocessed sample for 18 hours, and C is the viable cell count after culturing the processed sample for 18 hours.

Example 1 An emulsified stock solution having the following formulation was emulsified in water to prepare emulsions in which the pure content of CPTE was adjusted to 0.01% and 0.06%, respectively. After immersing a cotton cloth in this emulsion, the liquid was squeezed so that an amount of liquid equal to the weight of the cotton cloth adhered, and dried with hot air at 130 ° C. for 3 minutes to obtain a sample. In addition, this sample was
The sample was washed 10 times by the 217-103 method and used as a sample after washing. Table 1 shows the results. For the antibacterial test, MRSA and E. coli were used.

<Emulsion stock formulation> 20% CPTE 10% sodium polyoxyethylene nonylphenyl ether sulfonate (emulsifier) 10% hydrogenated castor oil EO (ethylene oxide) adduct (emulsifier) 20% Castor oil (solvent) 40% butyl diglycol (diethylene glycol monobutyl ether) (solvent)

On the other hand, parachlorometa-xylenol (abbreviated as PCMX) and 3- (trimethoxysilyl) quaternary ammonium silicone antibacterial agent were used as comparative control agents.
A sample and a sample after washing were prepared in the same manner as described above using propyl octadecyl dimethyl ammonium chloride (abbreviated as Si-QAC). The results are shown in Table 1.

[0046]

[Table 1] Chemicals and adhesion Amount of washed MRSA E. coli processed cloth (wt%) Number of inoculations Number of collections Number of inoculations Number of collections Yellowed untreated cloth 0 1 × 10 ⁶ 1 × 10 ⁸ 2 × 10 ⁶ 1 × 10 ⁸ None CPTE 0 1 × 10 ⁶ <10 ² 2 × 10 ⁶ <10 ² None 0.01 10 1 × 10 ⁶ 1 × 10 ³ 2 × 10 ⁶ 2 × 10 ⁴ None CPTE 0 1 × 10 ⁶ <10 ² 2 × 10 ⁶ <10 ² None 0.06 10 1 × 10 ⁶ <10 ² 2 × 10 ⁶ 3 × 10 ² None PCMX 0 1 × 10 ⁶ 1 × 10 ⁴ 2 × 10 ⁶ 4 × 10 ⁴ None 0.06 10 1 × 10 ⁶ > 10 ⁷ 2 × 10 ⁶ > 10 ⁷ None Si-QAC 0 1 × 10 ⁶ 1 × 10 ⁵ 2 × 10 ⁶ 5 × 10 ⁵ Large 0.06 10 1 × 10 ⁶ > 10 ⁶ 2 × 10 ⁶ > 10 ^{7 A} little

As is clear from Table 1, the samples treated with the emulsion containing CPTE maintained good antibacterial properties even after 10 washes. The comparative drug “PCMX”,
When "Si-QAC" was used, no antibacterial effect was observed after washing 10 times. When using "Si-QAC",
Yellowing was also observed.

Example 2 Based on the emulsified stock solution formulation of Example 1, the pure content of CPTE was 1.0
% Emulsion was prepared. In addition, a solvent formulation solution of 1% CPTE (base material) and 99% butyl diglycol (solvent) was prepared. Using a 100% polyester cloth, a sample was prepared in the same manner as in Example 1, and Staphylococcus was prepared.
An antibacterial test was performed on aureus FDA 209P strain. Table 2 shows the results.

[0049]

[Table 2] Emulsion solvent formulation solution Chemicals and washing Laundry S. aureus FDA 209P S. aureus FDA 209P amount (wt%) Number of inoculations Number of collections Number of inoculations Number of collections Unprocessed cloth 0 6 × 10 ⁵ 2 × 10 ⁸ 2 × 10 ⁶ 2 × 10 ⁸ CPTE 0 6 × 10 ⁵ <10 ² 2 × 10 ⁶ <10 ² 1.0 10 6 × 10 ⁵ 2 × 10 ⁵ 2 × 10 ⁶ 1 × 10 ⁵ PCMX 0 6 × 10 ⁵ > 10 ⁷ 2 × 10 ⁶ > 10 ⁷ 1.0 10 6 × 10 ⁵ > 10 ⁷ 2 × 10 ⁶ > 10 ⁷ Si-QAC 06 6 × 10 ⁵ > 10 ⁷ 2 × 10 ⁶ > 10 ⁷ 1.0 10 6 × 10 ⁵ > 10 ⁷ 2 × 10 ⁶ > 10 ⁷

As is clear from Table 2, the sample treated with the emulsion containing CPTE was a 100% polyester fiber having difficulty in adhering. The antibacterial property was maintained after washing 10 times. On the other hand, when the comparative drug was used,
Antibacterial properties could not be maintained before and after washing.

Example 3 An emulsion of 0.2% pure CPTE was prepared, and an etherified trimethylol melamine resin (“Sumitex Resin M-3”, manufactured by Sumitomo Chemical Co., Ltd., active ingredient 80%) was added to the emulsion.
% And an amine catalyst that promotes the condensation of the melamine resin (“Sumitex Accelerator ACX” manufactured by Sumitomo Chemical Co., Ltd.)
)) 0.2% was added to make a homogeneous solution. After dipping a 100% polyester cloth in this liquid, the cloth was squeezed so that a liquid of 70% of the weight of the cloth adhered, and dried with hot air at 130 ° C. for 3 minutes. This was repeatedly washed 10 times by the JIS L0217-103 method, and used as a sample after washing. As a control drug, parachlorometaxylenol (PCMX) was used. Table 4 shows the results
Shown in For the antibacterial test, MRSA and E. coli were used.

[0052]

[Table 3] Drug and adhesion Wash MRSA E. coli amount (wt%) Number of inoculations Number of collections Number of inoculations Number of collections No-work cloth 0 2 × 10 ⁵ 2 × 10 ⁸ 1 × 10 ⁶ 1 × 10 ⁸ log B / C Antibacterial evaluation log B / C Antibacterial evaluation CPTE 0 5.8 ○ 6.0 ○ 0.14 10 5.0 ○ 4.5 ○ PCMX 0 2.2 ○ 2.1 ○ 0.14 10 <2.0 × <2.0 ×

As is clear from Table 3, even if 0.14% of CPTE is selected and the appropriate amount is selected, the antibacterial effect is maintained even after washing 10 times. On the other hand, the comparative drug did not show any antibacterial effect after washing 10 times.

Example 4 An emulsified emulsion (prepared from the emulsified stock solution of Example 1) and a suspension of a suspension formulation (prepared from the following stock suspension) having a pure CPTE content of 0.9% were prepared. In this solution, 1.0% of etherified trimethylol melamine resin (“Sumitex Resin M-3” manufactured by Sumitomo Chemical Co., Ltd.) and an amine catalyst that promotes condensation of the melamine resin (“Sumitex Accelerator manufactured by Sumitomo Chemical Co., Ltd.”) ACX ") was added to obtain a homogeneous solution. A mixed spinning cloth of 35% polyester and 65% cotton was dipped in each liquid, squeezed so that a liquid of 70% of the weight of the cloth adhered, and dried with hot air at 170 ° C. for 1 minute. Further, this was repeatedly washed 0 to 100 times by JIS L0217: F-3 method + bleaching agent addition to obtain a sample after washing. As a control drug, parachlorometaxylenol (PCMX) was used. Table 4 shows the results obtained when MRSA was used.
Table 5 shows the results obtained when.

<Formulation of suspension stock solution> 10% CPTE (constituent) 3% nonylphenol EO phosphate sodium ester (dispersant) 0.1% sodium polyacrylate (thickener) 0.1% consumption Foam ・ 86.8% water

[0056]

[Table 4] Emulsion suspension medicine and adhesion Washing MRSA MRSA amount (wt%) Number of inoculations Number of collections Number of inoculations Number of collections No-work cloth 0 1 × 10 ⁶ 1 × 10 ⁸ 3 × 10 ⁶ 1 × 10 ⁸ CPTE 0 1 × 10 ⁶ <10 ² 3 × 10 ⁶ <10 ² 0.63 50 1 × 10 ⁶ <10 ² 3 × 10 ⁶ <10 ² 100 1 × 10 ⁶ <10 ² 3 × 10 ⁶ <10 ² PCMX 0 1 × 10 ⁶ <10 ² 3 × 10 ⁶ <10 ² 0.63 50 1 × 10 ⁶ 2 × 10 ⁸ 3 × 10 ⁶ 5 × 10 ⁸ 100 1 × 10 ⁶ 3 × 10 ⁸ 3 × 10 ⁶ 1 × 10 ⁸

[0057]

[Table 5] Emulsion suspension drug and adhesion Washing E. coli E. coli amount (wt%) Number of inoculations Number of collections Number of inoculations Number of collections Unprocessed cloth 0 1 × 10 ⁶ 1 × 10 ⁸ 3 × 10 ⁶ 1 × 10 ⁸ CPTE 0 1 × 10 ⁶ <10 ² 2 × 10 ⁶ <10 ² 0.63 50 1 × 10 ⁶ <10 ² 2 × 10 ⁶ <10 ² 100 1 × 10 ⁶ <10 ² 2 × 10 ⁶ <10 ² PCMX 0 1 × 10 ⁶ <10 ² 2 × 10 ⁶ <10 ² 0.63 50 1 × 10 ⁶ 5 × 10 ⁸ 2 × 10 ⁶ 7 × 10 ⁸ 100 1 × 10 ⁶ 4 × 10 ⁸ 2 × 10 ⁶ 2 × 10 ⁸

As shown in Tables 4 and 5, the CPTE
Is 0.63% of the drug if the resin and catalyst are selected in the right amount
Even with adhesion, both emulsions and suspensions were extremely harsh to JIS L0 for 35% polyester and 65% cotton mixed spinning cloth.
217: The antibacterial effect was maintained even after 100 washes with the F-3 method and the addition of a bleaching agent. On the other hand, for the control drug,
No antibacterial effect was observed after washing more than 50 times.

[0059]

As described in the section of the action, according to the present invention, not only natural fibers, but also regenerated or semi-synthetic fibers, and synthetic fibers, or fiber products made of blended fibers thereof, can be used. , The required amount of tebuconazole can be surely carried. The treated antibacterial fiber product is highly safe, has excellent antibacterial activity against various bacteria including drug-resistant Staphylococcus aureus and pathogenic Escherichia coli, and its antibacterial properties are not easily impaired even by washing . If the conditions are selected, the antibacterial activity is maintained even after, for example, 100 washes. In addition, the antibacterial fiber product of the present invention hardly causes yellowing or change in feeling even though the antibacterial treatment is performed, has no odor, and does not impair the original taste of the material fiber.

Claims (6)

[Claims] (1) α- [2- (4-chlorophenyl) ethyl] -α- (1,1-dimethylethyl) -1
H-1,2,4-triazole- (1) -ethanol (generic name: tebuconazole) or an antibacterial fiber product carrying the same and a binder resin. 2. An α- [2- (4-chlorophenyl) ethyl] -α- (1,1-dimethylethyl) -1H-1,
2,4-triazole- (1) -ethanol (generic name:
(Tevconazole) emulsifying, suspending or dissolving in a medium, contacting the textile with the treatment liquid, and then drying or drying and curing to impart antibacterial properties to the textile. Manufacturing method of antibacterial fiber products. 3. The method according to claim 2, wherein the treatment liquid is prepared by emulsifying, suspending or dissolving tebuconazole in a medium together with a binder resin. 4. The method according to claim 3, wherein the binder resin is a thermosetting or reactive resin. 5. A process in which tebuconazole is emulsified, suspended or dissolved in a medium together with a binder resin composed of a thermosetting or reactive resin and a catalyst for promoting the curability or reactivity of the resin as a treatment liquid. The method according to claim 4, wherein a liquid is used. 6. A binder resin comprising a thermosetting or reactive resin is an etherified methylol melamine resin,
The method according to claim 5, wherein the catalyst is an amine-based or metal salt-based catalyst.