JPH08226077A - Production of antimicrobial fiber or textile product - Google Patents

Abstract

PURPOSE: To obtain antimicrobial fibers or a textile product therefrom, excellent in washing resistance by imparting fibers or a product therefrom with a finishing liquid agent containing a water-soluble polyhexamethylenebiguanide-based compound, aqueous water-soluble resin dispersion(s) and crosslinking agent(s). CONSTITUTION: First, a finishing liquid agent is prepared by mixing water with a water-soluble polyhexamethylenebiguanide-based antibacterial agent, at least one kind of aqueous dispersion selected from those of polyvinyl alcohol and its copolymers, polyallylamine and its copolymers, diallylamine derivative polymers and copolymers, polyvinylpyrrolidone and its copolymers, water-soluble nylons and polyester resins (pref. aqueous dispersion of polyvinyl alcohol or its copolymer), and at least one kind of crosslinking agent crosslinkable with the above substances) selected from epoxy compounds, aziridine-based compounds and blocked isocyanate compounds (pref. epoxy compound). Next, fibers or a textile product therefrom is immersed in this agent followed by dehydration, drying and then heat treatment, thus imparting the fibers or the textile product with microbe-proofness.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention has excellent washing durability.
The present invention relates to a method for producing an antibacterial fiber or a fiber product.

[0002]

2. Description of the Related Art Antibacterial treatment for preventing discoloration of fibers, weakening of fibers, generation of bad odor, etc. due to propagation of microbes such as mold and bacteria in textiles such as underwear, socks, bed sheets and pillow covers. Fibers that have been subjected to are conventionally known.
Also, in recent years, so-called nosocomial infection, which is a contact infection with bacteria resistant to antibiotics and methicillin-resistant Staphylococcus aureus in hospitals and clinics, has become a social problem, and antibacterial processing of clothes such as sheets, lab coats and pajamas in hospitals. Is required.

As antibacterial agents used for these antibacterial treatments, benzalkonium chloride, polyoxyethylene trimethyl ammonium chloride, benzethonium chloride, cetyl pyridium chloride, alkyl trimethyl ammonium salt, p-isooctylphenoxyethoxyethyl dimethyl benzyl ammonium chloride, Quaternary ammonium salt-based antibacterial agents such as phenodedecium bromide, cetyldimethylammonium chloride, and 3- (trimethoxysilyl) propyloctadecyldimethylammonium chloride are generally used. However, these antibacterial agents have weak adhesiveness to fibers, and are almost removed by washing with a general synthetic detergent several times, resulting in low washing durability and loss of antibacterial effect. .

On the other hand, the polyhexamethylene biguanide compound is a high molecular weight water-soluble antibacterial agent in which a large number of biguanide groups and hexamethylene groups are alternately linked, and is particularly superior to the quaternary ammonium salt antibacterial agent. It is known that the antibacterial property in the presence of dirt is very excellent. However, like quaternary ammonium salt type antibacterial agents, it has weak adhesion to fibers and is almost removed by washing with a general synthetic detergent several times, resulting in low washing durability and loss of antibacterial effect. There was a flaw.

In order to improve the adherence of these antibacterial agents to fibers, various combinations with crosslinking agents for fibers have been tried. In JP-A-4-108180, a method of combining the quaternary ammonium salt-based antibacterial agent with a water-soluble melamine-based crosslinking agent has been attempted, but these quaternary ammonium salt-based antibacterial agents are water-soluble melamine-based crosslinking agents. Almost no chemical reaction took place with the agent, and no improvement in washing durability was observed even in the experiments conducted by the present inventors.
Water-soluble melamine compounds, glycoluril compounds,
Formaldehyde condensates such as urea resin compounds have been widely used as a treating agent for textile processing, such as imparting wrinkle resistance to textiles. In addition, it has been widely used in general industrial fields as a very excellent durability-imparting agent such as paint and coating on the surface of plastics, and a curing agent. However, products treated with these compounds
Since it releases a high concentration of formalin, it cannot be put to practical use with textile products that come into direct contact with the skin.

Japanese Patent Publication Nos. 61-45441 and 62
Japanese Patent Publication No. -60509 proposes a method of fixing a polyhexamethylene biguanide compound after treating the fiber with a polyacrylic acid ester or an anion group-containing polymer. However, in this method, since the pretreatment is required, the cost of the manufacturing process is high, and the washing durability is not sufficient.

JP-A-3-39310 discloses a method of preparing a processing emulsion by previously copolymerizing a polyhexamethylene biguanide compound with a sulfonic acid group-containing monomer and an acrylic ester. However, this method also has a problem that it takes time and cost to prepare the processing agent because it requires a polymerization step which is a preliminary reaction when preparing the processing agent.

[0008]

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention The present invention solves the problems of the prior art. That is, it is intended to provide a method for producing an antibacterial fiber or a textile product which does not release formalin and has high washing durability, and does not require a special pretreatment or a polymerization step and can be performed in a single single process. The purpose is to enable economical processing.

[0009]

[Means for Solving the Problems] The present inventors have completed the present invention as a result of intensive studies to solve the problems. That is, the present invention includes the following (a),
An antibacterial fiber characterized in that an aqueous solution containing (b) and (c) is adhered to the surface of a fiber or a fiber product, and a polyhexamethylene biguanide compound is fixed to the surface of the fiber in an insoluble state in water. It is a method of manufacturing a textile product. (A) Water-soluble polyhexamethylene biguanide compound (b) Water-soluble resin or water-based resin dispersion (c) (a) Water-soluble polyhexamethylene biguanide compound and (b) Water-soluble resin or (b) ) Crosslinking agent capable of undergoing a crosslinking reaction with the resin component of the aqueous resin dispersion

The water-soluble resin or water-based resin dispersion used in the present invention can coexist stably in an aqueous solution with a polyhexamethylene biguanide compound, which is a cationic polymer, and can undergo a crosslinking reaction in the molecule. Since it has various active groups, a cross-linking reaction by a cross-linking agent forms a three-dimensional cross-linked film on the fiber, which has a strong antibacterial activity and binds a biguanide group or a group containing the group. Succeeded in providing improved antibacterial power.

In the present invention, the water-soluble polyhexamethylene biguanide compound has a basic structure in which a plurality of hexamethylene groups are bonded via a biguanide group, and hexamethylene not bonded to the biguanide group. When there is an end of the, the end is amino, imino or amide, and the biguanide group, amino group or imino group is optionally or partially combined with an inorganic or organic acid residue to form a salt. It is a water-soluble polymer compound and has high antibacterial properties. It is preferable that the number of repeating basic units consisting of a biguanide group and a hexamethylene group is 2 to 100.

The water-soluble resin or aqueous resin dispersion includes polyvinyl alcohol or its copolymer, polyallylamine or its copolymer, diallylamine derivative polymer or its copolymer, polyvinylpyrrolidone or its copolymer, water-soluble resin. Aqueous nylon, polyester-based resin aqueous dispersions and the like have high stability in an aqueous solution with a polyhexamethylene biguanide compound, and can be effectively used in terms of reactivity with a crosslinking agent. In the present invention, the water-soluble resin or the water-based resin dispersion may be used alone or in combination of two or more.

As the polyvinyl alcohol or its copolymer used in the present invention, fully saponified or partially saponified polyvinyl alcohol, that is, vinyl alcohol / vinyl acetate copolymer, polyvinyl butyral, etc. may be mentioned as specific examples. it can. The degree of saponification is 70 due to water solubility, solution viscosity, and water resistance of the film after treatment.
To 99.9 mol% and the degree of polymerization of 300 to 2500 is preferable.

Specific examples of the polyallylamine or its copolymer used in the present invention include polyallylamine and its inorganic acid salts, and copolymers of monoallylamine and diallylamine. From the viewpoint of solution viscosity and water resistance of the coating film after treatment, those having a weight average molecular weight of 9,000 to 110,000 are preferable.

The polymer of the diallylamine derivative or its copolymer used in the present invention includes a polymer of diallyldimethylammonium chloride, a copolymer of this and acrylamide, a copolymer of this and sulfur dioxide,
Specific examples thereof include a copolymer of this and diallylamine in which the amine moiety is modified with epichlorohydrin. The weight average molecular weight of 2,000 to 160,000 is preferable in view of solution viscosity and water resistance of the film after treatment.

Specific examples of polyvinylpyrrolidone or a copolymer thereof used in the present invention include a polymer of vinylpyrrolidone, a copolymer of vinylpyrrolidone and vinyl acetate, and a copolymer of vinylpyrrolidone and acrylamide or acrylate. Can be mentioned as. From the viewpoint of the solution viscosity and the water resistance of the film after treatment, it is preferable that the K value (1% aqueous solution) shown in the technical data of BASF Japan Co., Ltd. is 15 to 100.

Specific examples of the water-soluble nylon used in the present invention include modified polyamides having solubility in water and alcohol. From the solution viscosity and the water resistance of the film after treatment, the weight average molecular weight is 2
000 to 110,000 are preferable.

As the polyester resin aqueous dispersion used in the present invention, a polyester ionomer having a polyalkylene oxide chain or a sulfonic acid group introduced into the molecule of a glycol component or an acid component and an emulsifier are used to disperse in water. Specific examples include polyester emulsions.

The cross-linking agent used in the present invention is a three-dimensional cross-linking agent containing a polyhexamethylene biguanide group on the fiber by a cross-linking reaction with an active group capable of cross-linking reaction in a molecule of a water-soluble resin or an aqueous resin dispersion. It forms a strong film, and imparts washing durability to the antibacterial activity of the fiber. Epoxy compounds, aziridine compounds, blocked isocyanate compounds and the like are suitable as the crosslinking agent in terms of reactivity, solubility, stability and the like. Further, in the present invention, these crosslinking agents may be used alone or in combination of two or more kinds.

The epoxy compound used in the present invention refers to a water-soluble compound or a water dispersion having two or more epoxy groups in the molecule, and includes aliphatic glycidyl ethers, glycidyl nitrogen compounds, carboxylic acid glycidyl ester. Classes and the like are preferable. Diethylene glycol diglycidyl ether, glycerin triglycidyl ether, polyglycerin polyglycidyl ether, glycerin (2
Specific examples thereof include -hydroxy) -1,3-diglycidyl ether and sorbitan glycidyl ether.

The aziridine compound used in the present invention refers to a water-soluble compound or an aqueous dispersion having an aziridine group in its molecule, and tetramethylolmethane-tri-β-
Specific examples thereof include aziridinyl propionate and N, N-hexamethylene-1,6-bis (1-aziridine) carboxamide.

The blocked isocyanate compound used in the present invention is a water-soluble or aqueous dispersion having a plurality of isocyanate groups in the molecule, and the reactive group is blocked with phenols, alcohols, sulfites or the like in water. Refers to those that have stability in.

The water-soluble resin or the aqueous resin dispersion and the crosslinking agent used in the present invention may be any one that can be used in an aqueous system and can stably coexist with the polyhexamethylene biguanide compound. It is not limited. Further, a catalyst may be used in combination for the purpose of improving crosslinkability. Furthermore, the reactivity is high and the usable time of the processing liquid is short,
When there is a problem in the process, pH adjustment or addition of a reactivity adjusting agent may be performed.

In the present invention, the amount of the antibacterial agent polyhexamethylene biguanide compound adhered to the fiber may be appropriately adjusted depending on the intended use and the desired antibacterial level, but generally 0 for the fiber. It is in the range of 0.001 to 5% by weight. Below this range, the antibacterial performance is lowered, and above this range, the manufacturing cost is high, and the texture of the fiber is impaired and the fiber is likely to fall off.

The fibers and fiber products in the present invention are:
Cotton, hemp, wool, silk, other natural fibers, chemical fibers such as rayon and suf, nylon, polyester, vinylon,
The fibers are so-called fiber products such as fibers themselves such as synthetic fibers such as acryl and the like, and woven fabrics, non-woven fabrics, non-woven fabrics, yarns or the like which are composed of the fibers.

In the present invention, the method for treating the fiber or the textile product with the treatment liquid containing the antibacterial agent depends on the form of the fiber to be used, but it is performed by a known method such as a dipping method, a padding method or a spray method. Later, if necessary mangle,
Excessive treatment liquid is removed by centrifugal dehydration or other method, and then the crosslinking reaction is promoted by drying, heating, etc.
It is preferable to provide a heat drying step at 70 ° C., preferably 100 to 170 ° C., since this leads to stable quality.

The treatment of the present invention can be carried out before or after dyeing, softening, resin processing, sewing, and other fiber treatments and fiber processings. Simultaneous processing with finishing and resin processing is also possible. Further, in the treatment liquid used in the present invention,
If necessary, a function-imparting agent such as a resin processing agent, a dye, a softening agent, an antistatic agent, a deodorant, an insect repellent, a water repellent, and an ultraviolet absorber may be added and used. When the stability of these function-imparting agents in the treatment liquid used in the present invention becomes a problem, a surfactant, a stabilizer and the like may be further added.

[0028]

EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited thereto.

[0029]

Example 1 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corporation),
10% aqueous solution of polyvinyl alcohol (Kuraray Co., Ltd.,
Poval PVA105 was prepared by heating and dissolving it in water. )
6 parts, 0.2 parts of polyglycerin polyglycidyl ether (SR-4GL, Sakamoto Yakuhin Kogyo Co., Ltd.), and 10 parts of water
0 parts were mixed to prepare a treatment liquid. A cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g / m ² ) was immersed in this at a bath ratio of 1:50 for 1 minute at room temperature and then spin-dried for 1 minute to give a squeezing ratio of about 100%. Was dried at 80 ° C. for 5 minutes and then heat-cured at 140 ° C. for 5 minutes. The antibacterial activity of the obtained treated cloth was evaluated according to the method for measuring the number of bacteria, which is described in the processing effect evaluation test manual for sanitary processed products of the Textile Products Sanitary Processing Council. As the test bacterium, S. aureus IFO12732 of Fermentation Research Institute was used. The results obtained are
The results are shown in Table 1 using the increase / decrease difference defined by the following formula, which is an index of antibacterial activity. Increase / decrease value difference = log (B / A) -log (C / A) where A is the number of bacteria measured when the bacterial dispersion was dispersed and recovered immediately after inoculation on the untreated cloth. B is the number of bacteria measured when the untreated cloth was inoculated with the bacterial dispersion, cultured for 18 hours, and then dispersed and collected.
C is the number of bacteria measured when the treated cloth was inoculated with the bacterial dispersion, cultured for 18 hours, and then dispersed and collected. Further, this treated cloth is washed with a household washing machine by a method according to JIS-0217 method 103 with a detergent (Lion Co., Ltd., Liquid High Top) 0.2% by weight of a washing liquid. After 5 minutes and 2 minutes of rinsing (40 ° C. rinsing water) twice as one cycle, washing was performed for 10 cycles and 25 cycles, and then naturally dried. The antibacterial activity of this treated cloth was evaluated in the same manner as above. The results are shown in Table 1.

[0030]

Example 2 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corp.),
10% aqueous solution of polyvinyl alcohol (Kuraray Co., Ltd.,
Poval PVA105 was prepared by heating and dissolving it in water. )
6 parts, 0.2 parts of aziridine-based crosslinking agent (Nippon Shokubai Co., Ltd., Chemitite PZ-33), and 100 parts of water are mixed,
A treatment liquid was prepared. A cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g / m ² ) was immersed in this at a bath ratio of 1:50 for 1 minute at room temperature, and then spin-dried for 1 minute to squeeze out about 100%.
This was dried at 80 ° C. for 5 minutes and then heat-cured at 140 ° C. for 5 minutes. The antibacterial activity of this treated cloth was evaluated in the same manner as in Example 1. The results are shown in Table 1. Also,
Washing was performed in the same manner as in Example 1 and the antibacterial activity was evaluated. The results are shown in Table 1.

[0031]

Example 3 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corp.),
10% aqueous solution of polyvinyl alcohol (Kuraray Co., Ltd.,
Poval PVA105 was prepared by heating and dissolving it in water. )
6 parts, 0.2 parts of a blocked isocyanate resin aqueous dispersion (Takeda Chemical Industries, Ltd., Prominate XC-910), and 100 parts of water were mixed to prepare a treatment liquid. Cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g / m ² )
Was immersed in a bath ratio of 1:50 at room temperature for 1 minute, centrifugally dehydrated for 1 minute to give a squeezing ratio of about 100%, dried at 80 ° C. for 5 minutes, and then heat-cured at 140 ° C. for 5 minutes. The antibacterial activity of this treated cloth was evaluated in the same manner as in Example 1. The results are shown in Table 1. In addition, washing was performed in the same manner as in Example 1 and the antibacterial activity was evaluated. The results are shown in Table 1.

[0032]

Example 4 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corp.),
1.5 parts of a 40% aqueous solution of polyallylamine hydrochloride (Nitto Boseki Co., Ltd., PAA-10L), polyglycerin polyglycidyl ether (Sakamoto Yakuhin Kogyo Co., Ltd., SR-4)
GL) 0.2 part and 100 parts of water were mixed to prepare a treatment liquid. A cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g / m ² ) was immersed in this at a bath ratio of 50 for 1 minute at room temperature and then spin-dried for 1 minute to give a squeezing ratio of about 100%. After drying at 80 ° C. for 5 minutes, it was heated and cured at 140 ° C. for 5 minutes. The antibacterial activity of this treated cloth was evaluated in the same manner as in Example 1. The results are shown in Table 1. In addition, Example 1
Washing was carried out in the same manner as above and the antibacterial activity was evaluated. The results are shown in Table 1.

[0033]

Example 5 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corp.),
1.5 parts of 35% aqueous solution of copolymer of diallyldimethylammonium chloride and diallylamine hydrochloride derivative (Nitto Boseki Co., Ltd., PAS-880), polyglycerin polyglycidyl ether (Sakamoto Yakuhin Kogyo Co., Ltd., SR-4)
GL) 0.2 part and 100 parts of water were mixed to prepare a treatment liquid. A cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g / m ² ) was immersed in this at a bath ratio of 1:50 at room temperature for 1 minute and then spin-dried for 1 minute to give a squeezing ratio of about 100%.
This was dried at 80 ° C. for 5 minutes and then heat-cured at 140 ° C. for 5 minutes. The antibacterial activity of this treated cloth was evaluated in the same manner as in Example 1. The results are shown in Table 1. In addition, washing was performed in the same manner as in Example 1 and the antibacterial activity was evaluated. The results are shown in Table 1.

[0034]

Example 6 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corp.),
6 parts of a 10% aqueous solution of polyvinylpyrrolidone (BASF Japan Ltd., prepared by dissolving rubiscol K17 in water), 0.2 parts of polyglycerin polyglycidyl ether (Sakamoto Yakuhin Kogyo Co., Ltd., SR-4GL), Also, 100 parts of water was mixed to prepare a treatment liquid. A cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g / m ² ) was immersed in this at a bath ratio of 1:50 for 1 minute at room temperature and then spin-dried for 1 minute to give a squeezing ratio of about 100%. Was dried at 80 ° C. for 5 minutes and then heat-cured at 140 ° C. for 5 minutes. The antibacterial activity of this treated cloth was evaluated in the same manner as in Example 1. The results are shown in Table 1. In addition, washing was performed in the same manner as in Example 1 and the antibacterial activity was evaluated. The results are shown in Table 1.

[0035]

Example 7 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corporation),
10% aqueous solution of water-soluble nylon resin (Toray Industries, Inc., AQ
-Nylon P-70 was prepared by dissolving it in water. 6 parts, polyglycerin polyglycidyl ether (Sakamoto Yakuhin Kogyo KK, SR-4GL) 0.2 parts, and water 100 parts were mixed to prepare a treatment liquid. Cotton cloth (color dye company)
The obtained gold width, 100 g / m ² ) was soaked at a bath ratio of 1:50 at room temperature for 1 minute, centrifugally dehydrated for 1 minute to give a squeezing ratio of about 100%, and dried at 80 ° C. for 5 minutes. 1
It was heat-cured at 40 ° C. for 5 minutes. This treated cloth is used in Example 1.
The antibacterial activity was evaluated in the same manner as in. The results are shown in Table 1. In addition, washing was performed in the same manner as in Example 1 and the antibacterial activity was evaluated. The results are shown in Table 1.

[0036]

Example 8 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corporation),
2 parts of a 30% aqueous solution of an aqueous aromatic polyester (Dainippon Ink and Finetex ES850), polyglycerin polyglycidyl ether (Sakamoto Yakuhin Kogyo Co., Ltd.,
SR-4GL) 0.2 part, and 100 parts of water are mixed,
A treatment liquid was prepared. A cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g / m ² ) was immersed in this at a bath ratio of 1:50 for 1 minute at room temperature, and then spin-dried for 1 minute to squeeze out about 100%.
This was dried at 80 ° C. for 5 minutes and then heat-cured at 140 ° C. for 5 minutes. The antibacterial activity of this treated cloth was evaluated in the same manner as in Example 1. The results are shown in Table 1. Also,
Washing was performed in the same manner as in Example 1 and the antibacterial activity was evaluated. The results are shown in Table 1.

[0037]

Comparative Example 1 2 parts of 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, Zeneca Corp.),
100 parts of water was mixed to prepare a treatment liquid. A cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g / m ² ) was immersed in this at a bath ratio of 1:50 for 1 minute at room temperature and then spin-dried for 1 minute to give a squeezing ratio of about 100%. Was dried at 80 ° C. for 5 minutes and then heat-cured at 140 ° C. for 5 minutes. The antibacterial activity of this treated cloth was evaluated in the same manner as in Example 1. The results are shown in Table 1. In addition, washing was performed in the same manner as in Example 1 and the antibacterial activity was evaluated. The results are shown in Table 1.

[0038]

Comparative Example 2 2 parts of a 20% aqueous solution of polyhexamethylene biguanide hydrochloride (Proxel IB, manufactured by Zeneca Corporation),
10% aqueous solution of polyvinyl alcohol (Kuraray Co., Ltd.,
Poval PVA105 was prepared by heating and dissolving it in water. )
A treatment liquid was prepared by mixing 6 parts and 100 parts of water.
On this, cotton cloth (gold cloth obtained from Shikiso Co., Ltd., 100 g
/ M ² ) at a bath ratio of 1:50, soaked at room temperature for 1 minute, and
Centrifuge and spin-dry for about 100% to 80%.
After being dried at 5 ° C for 5 minutes, it was heat-cured at 140 ° C for 5 minutes. The antibacterial activity of this treated cloth was evaluated in the same manner as in Example 1. The results are shown in Table 1. In addition, washing was performed in the same manner as in Example 1 and the antibacterial activity was evaluated. The results are shown in Table 1.

[0039]

[Table 1]

[0040]

As is clear from Table 1, a water-soluble polyhexamethylene biguanide compound is used as an aqueous solution of a water-soluble resin or a water-based resin dispersion and a crosslinking agent reactive therewith, and the solution is used as a fiber. Alternatively, it is possible to obtain a fiber and a fiber product having excellent anti-bacterial activity, which is excellent in washing durability by applying a crosslinking reaction after being applied to the fiber product.

Claims (4)

[Claims] 1. An aqueous solution containing the following (a), (b) and (c) is attached to the surface of a fiber or a fiber product, and a polyhexamethylene biguanide compound is fixed to the surface of the fiber in a state of being insoluble in water. A method for producing an antibacterial fiber or a fiber product, which comprises: (A) Water-soluble polyhexamethylene biguanide compound (b) Water-soluble resin or water-based resin dispersion (c) (a) Water-soluble polyhexamethylene biguanide compound and (b) Water-soluble resin or (b) ) Crosslinking agent capable of undergoing a crosslinking reaction with the resin component of the aqueous resin dispersion 2. A water-soluble resin or an aqueous resin dispersion comprising polyvinyl alcohol or a copolymer thereof, polyallylamine or a copolymer thereof, a polymer of a diallylamine derivative or a copolymer thereof, polyvinylpyrrolidone or a copolymer thereof, The method for producing an antibacterial fiber or a fiber product according to claim 1, comprising one or more selected from water-soluble nylon and an aqueous dispersion of polyester resin. 3. The antibacterial property according to claim 1 or 2, wherein the cross-linking agent comprises one kind or two or more kinds selected from an epoxy compound, an aziridine compound and a blocked isocyanate compound. A method of manufacturing a fiber or a textile product. 4. The water-soluble resin or the water-based resin dispersion is polyvinyl alcohol or a copolymer thereof, and the cross-linking agent is an epoxy compound, according to claim 1, claim 2 or claim 3. The method for producing an antibacterial fiber or textile product.