KR20210147762A - Antibacterial composition for textiles with imporved resistance to laundering - Google Patents

Abstract

The present invention relates to an antibacterial composition for textiles which can maintain antibacterial activity for a long period of time by being added during a rinsing process when textiles are being washed. By adding an antibacterial composition for textiles containing a novel polymer compound according to the present invention, as a textile softener, when textiles are washed using a general household washing machine, antibacterial properties can be easily imparted to various textiles. In addition, the antibacterial composition for textiles of the present invention can improve laundry resistance with respect to the textiles and maintain antibacterial activity for a long period of time.

Description

Antibacterial composition for textiles with improved washing resistance

The present invention relates to an antibacterial composition for textiles that can maintain antibacterial activity for a long period of time by adding it during a rinsing process when washing textiles.

In the early days of textile antibacterial processing, antibacterial agents were largely divided into aromatic halogen compounds, organosilicon quaternary ammonium salts, and other compounds. Among them, the most commonly used are metal or metal-containing inorganic particles, quaternary ammonium salts and organosilicon quaternary ammonium salts. Recently, chitin and chitosan have also been actively used.

As an example, Korean Patent Registration No. 10-0624069 discloses a method of manufacturing an antibacterial fiber nonwoven fabric by treating a nano-sized silver colloidal solution, which is an inorganic metal material. On the other hand, from wool fibers treated with N-dodecyl-N,N-dimethylglycine cysteamine hydrochloride (DABM), a quaternary ammonium surfactant, Bacillus fumirus ( B . pumilus ) has been reported to have antibacterial activity. In addition, it has been reported that citric acid (CA) and chitosan are used for durable press (DP) processing and antibacterial processing.

In general, antibacterial agents for textiles are mainly used for products that come in direct contact with the human body or are used for hygiene, such as hospital sheets, military uniforms, underwear, socks, scrubbers, and dishcloths. Antibacterial treatment can cause harm to the human body due to contamination by microorganisms. Accordingly, there is a need for an antibacterial agent capable of maintaining antibacterial activity for a long time by improving durability against washing.

In addition, according to the prior art related to the antibacterial agent for textiles, the majority of techniques for imparting antibacterial properties in the yarn stage or in textile dyeing and finishing (Pad-Cure), as well as quaternary ammonium with known antibacterial activity In the case of antibacterial substances such as surfactants, it is known that it is preferable not to use more than 0.5 g per 1 kg of general fibers because they are harmful.

Therefore, unlike the prior art that minimizes harmfulness and imparts antibacterial properties (antibacterial/antiviral) in the textile processing step, there is a need to develop an antibacterial agent for textiles that can easily impart antibacterial properties to fibers in the rinsing step after washing. am.

KR 10-0624069 B1

Accordingly, the present inventors have researched to develop an antibacterial composition for textiles that is differentiated from the prior art that imparts antibacterial properties in the textile processing step and has improved washing resistance at the same time. The present invention was completed by confirming that when the antibacterial composition for textiles was treated, it had a continuous antibacterial effect on various microorganisms in various textile materials.

In order to achieve the above object, the present invention provides an antibacterial composition for fibers containing any one or more of the compounds represented by the following [Formula 1] to [Formula 2]:

[Formula 1]

[Formula 2]

In the above [Formula 1],

R ₁ is an alkyl ether, an amine or an amine salt,

a and b are each a molar ratio of the monomers, a is 0 to 20%, b is 100 to 80%,

In the above [Formula 2],

x represents 10 to 500 repeating units.

By using the antibacterial composition for textiles according to the present invention, it is possible to overcome the disadvantages of the prior art of imparting antibacterial properties in the yarn stage or in dyeing and post-processing using special expensive chemicals, tools and instruments in the textile industry. have. That is, the general public can easily impart antibacterial properties to various textile materials by using a general household washing machine to the fibers to which antibacterial properties are or is not imparted.

In addition, the antibacterial composition for fibers according to the present invention can be physically combined with various fiber materials such as cellulosic fibers, nylon, and polyester with weight deduction, in particular, fibers such as cotton or knitted fabrics and nylon by electrostatic attraction. Thus, washing resistance is improved and antibacterial activity can be maintained for a long time.

One aspect of the present invention provides an antibacterial composition for fibers containing any one or more of the compounds represented by the following [Formula 1] to [Formula 2]:

[Formula 1]

[Formula 2]

In the above [Formula 1],

R ₁ is an alkyl ether, an amine or an amine salt,

a and b are each a molar ratio of the monomers, a is 0 to 20%, b is 100 to 80%,

In the above [Formula 2],

x represents 10 to 500 repeating units.

As used herein, the term "antibacterial" refers to inhibiting the growth or growth of all microorganisms having a harmful effect, and the microorganism may be Gram-positive or Gram-negative.

The Gram-positive bacteria are not limited thereto, but may be Staphylococcus aureus , Bacillus subtilis , Staphylococcus epidermidis , or Listeria monocytogenes .

The Gram-negative bacteria are, but are not limited to , Escherichia coli , Salmonella typhimurium , Klebsiella pneumoniae , Pseudomonas aeruginosa , Shigella sonnei , Shigella sonnei, Neisseria gonorrhoeae . Clostridium difficile ( Clostridium difficile ) or Yersinia pestis may be.

In addition, in the present specification, the antibacterial is used in the same context as mildew resistance or antiviral, and it means comprehensively inhibiting the growth or growth of all harmful bacteria such as microorganisms, fungi, and viruses.

In one embodiment of the invention, the antimicrobial composition comprises Staphylococcus aureus (Staphylococcus aureus, ATCC 6538), Klebsiella pneumoniae for the fiber (Klebsiella pneumoniae, ATCC 4352), Escherichia coli , ATCC 25922), Salmonella ( Salomonella typhimurium , KCTC 1925), characterized in that with antibacterial activity against Pseudomonas aeruginosa (Pseudomonas aeruginosa, ATCC 27853) and penicillin-resistant Staphylococcus aureus (Staphylococcus aureus, ATCC 33591).

The antibacterial composition for textiles containing at least one of the compounds represented by the above [Formula 1] to [Formula 2] may be a fabric softener added during the rinsing process during washing.

As used herein, the term "fabric softener" is a laundry aid used in the final rinse after washing, and is used interchangeably with fabric rinse aid. In general, fabric softeners are widely used at home for flexibility, wrinkle prevention, and antistatic protection of textile products after washing, but the main purpose of the present invention is to impart antibacterial and deodorizing properties to clothes or textile products after washing.

The antimicrobial composition for fibers of the present invention is in an amount of 0.01 to 20% by weight, 0.05 to 10% by weight, 0.1 to 5% by weight, 0.5 to 4% by weight, or 1 to 3% by weight relative to the fiber weight (owf, on weight fabric) It can be added during the rinsing process during washing.

In addition, the antibacterial composition for textiles of the present invention is from the group consisting of polydiallyldimethylammonium chloride, alkyl chloride (C12-C18) benzyldimethylammonium and alkyl chloride (C12-C18) dimethylethylbenzylammonium. It may further include one or more selected substances.

The average molecular weight of the polydiallyldimethylammonium chloride is not limited thereto, but may be 500 to 500,000 g/mol, 800 to 400,000 g/mol, or 1,000 to 300,000 g/mol.

The polydiallyldimethylammonium chloride may impart flexibility to the fiber, and thus may be suitable as an additional component of an antibacterial rinse.

The antibacterial composition for textiles of the present invention may have a deodorizing function. Common odor-causing substances that cause discomfort in clothes or textiles include ammonia, trimethylamine, acetic acid, hydrogen sulfide, and methylmercaptane. In addition, there are cigarette odors in daily life made up of various combinations of ingredients, food waste odors, sweat odors, and odors caused by metabolism of bacteria or mold.

In the present invention, the deodorizing target may be, but not limited to, ammonia, trimethylamine, hydrogen sulfide, acetic acid, methyl mercaptan, preferably ammonia.

The compound represented by [Formula 1] of the present invention may be a copolymer of an allyl monomer and diallyldimethylammonium chloride, for example, a random copolymer. The copolymer may be polymerized by a radical initiator.

Specifically, the allyl monomer may be, but is not limited to, allylamine hydrochloride. A person skilled in the art will be able to prepare the compound of [Formula 1] of the present invention by appropriately selecting various allyl monomers other than the allylamine hydrochloride, and under suitable reaction conditions.

The molar ratios a and b of the monomers in [Formula 1] of the present invention are not limited thereto, but each a may be 0 to 20%, 3 to 20%, 5 to 15%, or 10 to 15%, and b is 100 to 80%, 97 to 80%, 95 to 85% or 90 to 85%.

The average molecular weight of the copolymer represented by Formula 1 is not limited thereto, but may be 500 to 100,000 g/mol, 800 to 400,000 g/mol, or 1,000 to 300,000 g/mol.

The compound represented by [Formula 2] of the present invention may be a copolymer of methylamine and epichlorohydrin. In this case, epichlorohydrin may have a ratio of 1 to 1.5 moles based on 1 mole of methylamine.

The repeating unit x in [Formula 2] is not limited thereto, but may be 10 to 500, 50 to 500, 100 to 500, or 200 to 400.

The methylamine may be monomethylamine, and in the case of monomethylamine, the compound represented by [Formula 2] may have a form of a network polymer. The polymer of [Formula 2] may have a number average molecular weight of ^{5 × 10 3} to 1 × 10 ^{4 g/mol.} In addition, the polymer can be prepared by a known polymerization method, and can be prepared based on the manufacturing method described in Korean Patent No. 10-1864962.

When the antibacterial composition for textiles of the present invention is used as a laundry aid, it is possible to easily impart antibacterial, anti-fouling or antiviral properties to clothes or textile products using a home washing machine.

As used herein, the term "textile" is a long, thin, and softly bendable natural or artificial wire object, which is not only a raw material for textiles, but also a raw material for textile products such as ropes and nets, and a raw material for papermaking. is used as

In the present specification, the fiber is used in the same context as clothing or textile products, and refers to all products manufactured using fibers as a raw material.

Specifically, the fiber may be one or more selected from the group consisting of cotton, nylon, polyester, wool, and silk, but is not limited thereto.

The antibacterial composition for textiles of the present invention can be used as an antibacterial rinse by using any one or more of the compounds represented by [Formula 1] to [Formula 2] alone or in combination during washing during washing, and the dyed dye may be used as an antibacterial rinse. Fibers exposed to the surface and exhibiting anionic properties, such as nylon, may be added together with citric acid.

The antibacterial composition for textiles of the present invention can easily impart antibacterial properties to fibers by adding them during the rinsing process when washing using a normal washing machine at home without any special equipment used to impart antibacterial properties to fibers in the textile industry. can

In general, bacteria or mold are sterilized or sterilized during textile washing using a commercially available laundry detergent for clothes, but it is common that continuous antibacterial properties are not provided after washing. On the other hand, when the antibacterial composition of the present invention is administered during the rinsing process during washing, the antibacterial effect can be maintained by remaining in clothes or textile products after washing.

Specifically, even if bacteria or mold is sterilized or sterilized through washing, exposure to harmful bacteria such as various viruses, bacteria and fungi from the living environment after washing causes the harmful bacteria to parasitize on the fabric, causing sensitive troubles, such as skin allergies, When the antibacterial composition of the present invention is added during the rinsing process during washing, it is possible to continuously impart antibacterial properties by preventing harmful bacteria from parasitizing the fabric even after washing.

More specifically, the compound represented by [Formula 1] to [Formula 2] contained in the antibacterial composition for fibers of the present invention is resistant to electrostatic attraction with various types of fibers such as cellulosic fibers, nylon, and reduced-weight polyester. Because physical bonding is possible, it has washing resistance and can continuously maintain antibacterial properties even after washing 2 or more, 5 or more, 10 or more, 20 or more, or 50 or more times.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1. Preparation of cationic random copolymer

A stirrer, a cooler, and a thermometer were installed in a 4-neck flask with a capacity of 1.0 L. 100 g of 65% diallyldimethylammonium chloride and 5 g of allylamine hydrogenchloride salt were diluted with 60 g of distilled water, which was referred to as a monomer mix. 18 g of distilled water and a monomer mix were added to the flask and circulated with nitrogen gas. APS solution was prepared by diluting 1.1 g of ammonium persulfate (APS) in 70 g of distilled water.

The temperature was raised to 72 °C while circulating nitrogen, and the APS solution was added dropwise to the monomer mix at 72 °C to 74 °C for 5 hours. After holding at 75° C. for an additional 3 hours, it was cooled to room temperature. Distilled water is added so that the concentration of the reactor becomes 20% by weight of solid content, and the mixture is stirred for 10 minutes to obtain a random copolymer of polydialyldimethylammonium chloride and allylamine hydrochloride having the following [Formula 1] It was obtained at a concentration of 20%.

[Formula 1]

Preparation Example 2. Preparation of Cationic Polyamine Polymer

A stirrer, a condenser, and a thermometer were installed in a 4-neck flask with a capacity of 1.0 L. 100 g of distilled water and 100 g of 40% monomethylamine aqueous solution were placed in a reactor and stirred at 10°C. After 60 g of epichlorohydrin was added dropwise at less than 45° C. for 120 minutes with a metering pump, 44 g of epichlorohydrin was added dropwise at less than 85° C. for 50 minutes with a metering pump. Then, 2.6 g of a 36% aqueous solution of caustic soda was added dropwise through a metering pump for 95 minutes, and then cooled to room temperature. Distilled water was added so that the concentration of the reactor became 20% by weight of solids, and the mixture was stirred for 10 minutes to obtain a polyamine polymer having the following [Formula 2] at a concentration of 20%.

[Formula 2]

Example 1. Analysis of antibacterial effect of 2.5% (o.w.f) cationic random copolymer

After the main washing with detergent in the washing machine, 2.5% of the fiber weight by weight of the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 in the subsequent rinsing process (rinsing temperature 20 ° C to 40 ° C) ( owf, on weight fabric) was added and rinsed at 20°C to 40°C for 10 minutes. After rinsing, dehydration, and drying using a general drying or household washing and drying machine, the antibacterial (anti-mildew/antiviral) was evaluated as the bacteriostatic reduction rate (KS K 0693:2016). On the other hand, in the case of the control group, washing, rinsing, dehydration and drying were performed in the same manner without administering the cationic random copolymer of [Formula 1]. The results are shown in Table 1 below.

The standard cloth used for antibacterial evaluation was cotton, and 0.05% of Tween 80 as a nonionic surfactant was added to the inoculum solution to conduct the experiment. On the other hand, the concentration unit for the inoculum is dogs/mL.

control Test group (Preparation Example 1) strain 1
initial number of bacteria 2.2 × 10 ⁴ 2.2 × 10 ⁴ Bacteria count after 18 hours 9.8 × 10 ⁶ < 10 bacteriostatic reduction rate - 99.9% strain 2 initial number of bacteria 2.2 × 10 ⁴ 2.2 × 10 ⁴ Bacteria count after 18 hours 3.8 × 10 ⁷ < 10 bacteriostatic reduction rate - 99.9%

* Strain 1: Staphylococcus aureus (Staphylococcus aureus, ATCC 6538)

* Strain 2: Klebsiella pneumoniae ATCC 4352)

Example 2. Analysis of the antibacterial effect of 1.5% (o.w.f) cationic random copolymer

Washing, dehydrating and drying were performed under the same conditions as in Example 1 except that 1.5% of the fiber weight (owf, on weight fabric) was added to the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 by weight. After carrying out, the antibacterial property was evaluated by the bacteriostatic reduction rate (KS K 0693:2016). The results are shown in Table 2 below.

Example 3. Analysis of antibacterial effect of PDADMAC cationic polymer

The same conditions as in Example 1, except that 2.0% of the fiber weight (owf, on weight fabric) of a polydiallyldimethylammonium chloride (PDADMAC) cationic polymer having an average molecular weight of 10,000 to 500,000 was added by weight After washing, dehydration, and drying with a vacuum cleaner, the antibacterial property was evaluated by the bacteriostatic reduction rate (KS K 0693:2016). The results are shown in Table 2 below.

Example 4. Analysis of antibacterial effect of 2.0% (o.w.f) cationic random copolymer

Washing, dehydrating and drying were performed under the same conditions as in Example 1 except that 2.0% (owf, on weight fabric) of the fiber weight by weight of the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 was added. After carrying out, the antibacterial property was evaluated by the bacteriostatic reduction rate (KS K 0693:2016). The results are shown in Table 2 below.

Example 5. Analysis of antibacterial effect of cationic polyamine polymer

Washing, dehydrating and drying were carried out under the same conditions as in Example 1, except that 2.5% (owf, on weight fabric) of the cationic polyamine polymer of [Formula 2] obtained from Preparation Example 2 was added by weight. Afterwards, the antibacterial property was evaluated by the bacteriostatic reduction rate (KS K 0693:2016). The results are shown in Table 2 below.

Example 6. Analysis of the antibacterial effect of a mixture of cationic random copolymer and alkyl(C12-C18)benzyldimethylammonium chloride

After diluting the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 with a 5% concentration of alkyl (C12-C18)benzyldimethylammonium at a weight ratio of 1:1, the diluted solution was diluted by weight of the fiber weight. After washing, dehydration and drying under the same conditions as in Example 1 except for adding 1.5% (owf, on weight fabric), the antibacterial properties were evaluated as the bacteriostatic reduction rate (KS K 0693:2016). The results are shown in Table 2 below.

Example 7. Analysis of the antimicrobial effect of a mixture of cationic polyamine polymer and alkyl(C12-C18)dimethylethylbenzylammonium chloride

After diluting the cationic polyamine polymer of [Formula 2] obtained from Preparation Example 2 and a 5% concentration of alkyl (C12-C18)dimethylethylbenzylammonium in a weight ratio of 1: 1 by weight, the diluted solution was diluted by weight of the fiber weight. After washing, dehydration and drying under the same conditions as in Example 1 except for adding 2.5% (owf, on weight fabric), the antibacterial property was evaluated as a bacteriostatic reduction rate (KS K 0693:2016). The results are shown in Table 2 below.

unprocessed Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 strain 1 71.6% 99.3% 99.6% 99.0% 99.7% 99.9% 99.9% strain 2 88.2% 99.0% 99.4% 99.2% 99.9% 99.9% 99.9%

* Test environment: temperature (25 ± 10)℃, relative humidity (60 ± 30)%

* Strain 1: Staphylococcus aureus (Staphylococcus aureus, ATCC 6538)

* Strain 2: Klebsiella pneumoniae ATCC 4352)

* Inoculum concentration: 1.2 × 10 ⁵ cells/mL for strain 1, 1.3 × 10 ^{5 cells/mL for strain 2}

According to the results of Table 2, each of the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 and the cationic polyamine polymer of [Formula 2] obtained from Preparation Example 2 was washed with an antibacterial rinse in the rinsing step. It was found that by administering it as an antibacterial agent, antibacterial properties against harmful bacteria such as Staphylococcus aureus and Bacillus pneumoniae can be imparted to the fiber.

Example 8. Analysis of the deodorizing effect of PDADMAC cationic polymer

After the main washing with detergent in the washing machine, 20% (w/w) polydiallyldimethylammonium chloride having a molecular weight of 1,000 to 300,000 was used in the rinsing process (rinsing temperature room temperature to 60° C.) by weight of 2.5 of the fiber weight % (owf, on weight fabric) was added and the rinse process was performed at room temperature to 60°C for 10 minutes. After rinsing, dehydration and drying using a general drying or household washing and drying machine were evaluated for deodorizing properties against ammonia, hydrogen sulfide and acetic acid (Japanese Textile Evaluation and Testing Association Test Method (JTECE)). On the other hand, in the case of the control group, the fibers were not treated with 20% (w/w) polydiallyldimethylammonium chloride, and washing, rinsing, dehydration and drying were performed in the same manner. The results are shown in Table 3 below.

deodorizing substances Concentration unit (mg/kg) control test group ammonia initial concentration 100.0 100.0 concentration after 2 hours 99.3 0 Decrease rate (%) - 99.9 hydrogen sulfide initial concentration 4.0 4.0 concentration after 2 hours 3.8 0 Decrease rate (%) - 99.9 acetic acid initial concentration 30.0 30.0 concentration after 2 hours 29.4 0 Decrease rate (%) - 99.9

* Test method: Put a 10 cm × 10 cm cotton standard cloth in a 5 L tetra bag, inject 3 L of gas with the initial concentration adjusted, and measure the gas concentration 2 hours later with a detection tube

* Used detection tube: Ammonia detection tube 3La, hydrogen sulfide detection tube 4-LT, acetic acid detection tube 81L

* Measurement time: after 2 hours

* Deodorization rate (%) = [(Cb - Cs)/Cb] × 100

* Cb: Blank, the concentration of test gas remaining in the test gas bag after 2 hours

* Cs: the concentration of the test gas remaining in the test gas bag after 2 hours of antibacterial rinse (sample of Example 9)

Example 9. Analysis of the antibacterial effect of cationic random copolymers against various strains

After the main washing with detergent in the washing machine, 2.5% (owf, owf, on weight fabric) and rinsed at room temperature to 60°C for 10 minutes. After rinsing, dehydration, and drying using a general drying or household washing and drying machine, the antibacterial property was evaluated by the bacteriostatic reduction rate (KS K 0693:2016). On the other hand, in the case of the control group, washing, rinsing, dehydration and drying were performed in the same manner without administering the cationic random copolymer of [Formula 1]. The results are shown in Table 4 below.

The standard cloth used for the antibacterial evaluation was cotton, and 0.05% of Tween 80 as a nonionic surfactant was added to the inoculum solution. On the other hand, the concentration unit for the inoculum is dogs/mL.

control test group strain 1 initial number of bacteria 2.2 × 10 ⁴ 2.2 × 10 ⁴ Bacteria count after 18 hours 9.8 × 10 ⁶ < 10 bacteriostatic reduction rate - 99.9% strain 2 initial number of bacteria 2.2 × 10 ⁴ 2.2 × 10 ⁴ Bacteria count after 18 hours 3.8 × 10 ⁷ < 10 bacteriostatic reduction rate - 99.9% strain 3 initial number of bacteria 2.2 × 10 ⁴ 2.2 × 10 ⁴ Bacteria count after 18 hours 3.6 × 10 ⁷ 1.0 × 10 ³ bacteriostatic reduction rate - 99.9% strain 4 initial number of bacteria 2.2 × 10 ⁴ 2.2 × 10 ⁴ Bacteria count after 18 hours 4.1 × 10 ⁷ < 10 bacteriostatic reduction rate - 99.9% strain 5 initial number of bacteria 1.8 × 10 ⁴ 1.8 × 10 ⁴ Bacteria count after 18 hours 3.1 × 10 ⁷ 1.6 × 10 ⁴ bacteriostatic reduction rate - 99.9% strain 6 initial number of bacteria 2.2 × 10 ⁴ 2.2 × 10 ⁴ Bacteria count after 18 hours 3.5 × 10 ⁷ 2.2 × 10 ³ bacteriostatic reduction rate - 99.9%

* Strain 1: Staphylococcus aureus (Staphylococcus aureus, ATCC 6538)

* Strain 2: Klebsiella pneumoniae ATCC 4352)

* Strain 3: Escherichia coli ( Escherichia coli , ATCC 25922)

* Strain 4: Salmonella ( Salomonella typhimurium , KCTC 1925)

* Strain 5: Pseudomonas aeruginosa (Pseudomonas aeruginosa, ATCC 27853)

* Strain 6: Penicillin-resistant Staphylococcus aureus ( Staphylococcus aureus , ATCC 33591 [ Methicillin-resistant strains of Staphylococcus aureus ])

According to the results of Table 4, by administering the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 as an antibacterial rinse in the rinsing step during washing, Staphylococcus aureus, Bacillus pneumoniae, Escherichia coli, Salmonella, Pseudomonas aeruginosa , it was found that antibacterial properties can be imparted to various bacteria such as penicillin-resistant Staphylococcus aureus.

Example 10. Analysis of the antibacterial effect of cationic random copolymers on various fiber types

The main washing was performed in a washing machine with detergent, and then the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 in the rinsing process (rinsing temperature room temperature ~ 60 ° C) was weighed by weight of each of cotton fiber, nylon and polyester 2.5% of the weight of the fiber (owf, on weight fabric) was added and rinsed at room temperature to 60°C for 10 minutes. After rinsing, dehydration, and drying using general drying (natural drying), iron drying, or a household washing and drying machine, the antibacterial property was evaluated by the bacteriostatic reduction rate (KS K 0693:2016). On the other hand, in the case of the control group, washing, rinsing, dehydration and drying were performed in the same manner without administering the cationic random copolymer of [Formula 1]. The results are shown in Tables 5 to 7 below.

Antimicrobial evaluation was performed by adding 0.05% of Tween 80 to the inoculum solution as a nonionic surfactant. On the other hand, the concentration unit for the inoculum is dogs/mL.

Cotton
control test group dry naturally iron drying strain 1 initial number of bacteria 1.8 × 10 ⁴ 1.8 × 10 ⁴ 1.8 × 10 ⁴ Bacteria count after 18 hours 9.8 × 10 ⁶ < 10 < 10 bacteriostatic reduction rate - 99.9% 99.9% strain 2 initial number of bacteria 1.9 × 10 ⁴ 1.9 × 10 ⁴ 1.9 × 10 ⁴ Bacteria count after 18 hours 3.8 × 10 ⁷ < 10 < 10 bacteriostatic reduction rate - 99.9% 99.9%

Nylon control test group dry naturally dryer drying strain 1 initial number of bacteria 1.8 × 10 ⁴ 1.8 × 10 ⁴ 1.8 × 10 ⁴ Bacteria count after 18 hours 9.8 × 10 ⁶ < 10 < 10 bacteriostatic reduction rate - 99.9% 99.9% strain 2 initial number of bacteria 1.9 × 10 ⁴ 1.9 × 10 ⁴ 1.9 × 10 ⁴ Bacteria count after 18 hours 3.8 × 10 ⁷ < 10 < 10 bacteriostatic reduction rate - 99.9% 99.9%

Polyester control test group dry naturally dryer drying strain 1 initial number of bacteria 1.8 × 10 ⁴ 1.8 × 10 ⁴ 1.8 × 10 ⁴ Bacteria count after 18 hours 9.8 × 10 ⁶ < 10 < 10 bacteriostatic reduction rate - 99.9% 99.9% strain 2 initial number of bacteria 1.9 × 10 ⁴ 1.9 × 10 ⁴ 1.9 × 10 ⁴ Bacteria count after 18 hours 3.8 × 10 ⁷ < 10 < 10 bacteriostatic reduction rate - 99.9% 99.9%

* Strain 1: Staphylococcus aureus (Staphylococcus aureus, ATCC 6538)

* Strain 2: Klebsiella pneumoniae ATCC 4352)

According to the results of Tables 5 to 7, by administering the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 as an antibacterial rinse in the rinsing step during washing, it is applied to various fiber materials such as cotton, nylon, and polyester. It was found that excellent antibacterial properties can be provided.

Example 11. Evaluation of washing resistance of a cationic random copolymer having an antibacterial effect

After the main washing with detergent in the washing machine, 2.5% (owf, owf, on weight fabric) and rinsed at room temperature to 60°C for 10 minutes. After rinsing, dehydration, and drying (KS K ISO 6330:2012, 5B [(41 ± 3)℃, horizontal mesh drying) using a household washing machine and washing machine 10 times repeatedly, antibacterial and bacteriostatic reduction ( KS K 0693:2016). Washing resistance was analyzed by evaluating the antibacterial effect according to the number of washings. On the other hand, in the case of the control group, washing, rinsing, dehydration and drying were performed in the same manner without administering the cationic random copolymer of [Formula 1]. The results are shown in Table 8 below.

The fibers used for the antimicrobial evaluation were cotton, polyester, and nylon, and 0.05% of Tween 80 as a nonionic surfactant was added to the inoculum solution. On the other hand, the unit of concentration for the inoculum is dogs/mL.

Cotton control test group After 10 washes strain 1 initial number of bacteria 1.8 × 10 ^{4 -} Bacteria count after 18 hours 9.8 × 10 ⁶ < 10 bacteriostatic reduction rate - 99.9% strain 2 initial number of bacteria 1.9 × 10 ^{4 -} Bacteria count after 18 hours 3.8 × 10 ⁷ < 10 bacteriostatic reduction rate - 99.9% Polyester
control test group After 10 washes strain 1 initial number of bacteria 1.8 × 10 ⁴ - Bacteria count after 18 hours 9.3 × 10 ⁶ < 10 bacteriostatic reduction rate - 99.9% strain 2 initial number of bacteria 1.9 × 10 ⁴ - Bacteria count after 18 hours 3.3 × 10 ⁷ < 10 bacteriostatic reduction rate - 99.9% Nylon control test group After 10 washes strain 1 initial number of bacteria 1.8 × 10 ⁴ - Bacteria count after 18 hours 9.8 × 10 ⁶ 1.2 × 10 ⁴ bacteriostatic reduction rate - 99.9% strain 2 initial number of bacteria 1.9 × 10 ⁴ 1.9 × 10 ⁴ Bacteria count after 18 hours 3.8 × 10 ⁷ < 10 bacteriostatic reduction rate - 99.9%

* Strain 1: Staphylococcus aureus (Staphylococcus aureus, ATCC 6538)

* Strain 2: Klebsiella pneumoniae , ATCC 4352)

* Washing conditions: KS K ISO 6330:2012, 5B [(41 ± 3)℃, horizontal mesh drying]

According to the results of Table 8, when the cationic random copolymer of [Formula 1] obtained from Preparation Example 1 is added in the washing and rinsing step, harmful bacteria such as Staphylococcus aureus and pneumococcus pneumoniae even after repeated washing 10 times or more It was found that the antibacterial activity against Accordingly, it was found that the cationic random copolymer of [Formula 1] can be usefully used as an active ingredient of the fiber antibacterial rinse, and also has excellent washing resistance.

Claims (8)

Antibacterial composition for fibers containing any one or more of the compounds represented by the following [Formula 1] to [Formula 2]:
[Formula 1]

[Formula 2]

In the above [Formula 1],
R ₁ is an alkyl ether, an amine or an amine salt,
a and b are each a molar ratio of the monomers, a is 0 to 20%, b is 100 to 80%,
In the above [Formula 2],
x represents 10 to 500 repeating units. According to claim 1,
The composition is an antibacterial composition for textiles, which is a fabric softener that is added in the rinsing process during washing. 3. The method of claim 2,
The composition is added in the rinsing process in an amount of 0.01 to 20% by weight based on the weight of the fiber, the antibacterial composition for fibers. According to claim 1,
In the composition, one or more substances selected from the group consisting of polydiallyldimethylammonium chloride, alkyl chloride (C12-C18) benzyldimethylammonium and alkyl chloride (C12-C18) dimethylethylbenzylammonium are added. Including, an antibacterial composition for textiles. According to claim 1,
The composition has a deodorizing function, an antibacterial composition for textiles. 6. The method of claim 5,
The deodorizing target is at least one selected from the group consisting of ammonia, acetic acid and hydrogen sulfide, an antibacterial composition for textiles. According to claim 1,
The compound represented by [Formula 1] is a random copolymer, an antibacterial composition for fibers. According to claim 1,
The fiber is at least one selected from the group consisting of cotton, nylon, polyester, wool and silk, antibacterial composition for fibers.