JP3065606B1 - Latent antibacterial agent - Google Patents

Abstract

A latent antimicrobial compound is provided. It also provides antibacterial cellulosic products. SOLUTION: A latent antibacterial compound is obtained by reacting a polyol containing one or more carboxyl groups, a polyol containing no carboxyl group, and polyisocyanate. In addition, such a latent antibacterial compound is contained in a cellulosic product and heated at an activation temperature to obtain an antibacterial cellulosic product.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a latent antibacterial agent, a cellulosic product containing the latent antibacterial agent, and an antibacterial cellulose product.

[0002]

2. Description of the Related Art In recent years, problems caused by bacteria such as hospital-acquired infections and food poisoning have become a social problem, and antibacterial products have been actively developed in order to respond to the problems.

At present, compounds used as antibacterial agents for fibers and paper include quaternary ammonium salts such as benzalkonium chloride, polybiguanide compounds, metal complex compounds, and aromatic halogen compounds such as trichlorocarbanide. And the like.

[0004]

However, since the above compounds are used as disinfectants in medical institutions and factories, when treating the fibers or paper with the antibacterial agent, the antibacterial agent is not used by the worker. Touching the hand or body of the patient may cause skin irritation and dermatitis, which is a problem. Further, contact with fibers or paper containing an antibacterial agent may cause skin irritation or dermatitis, which is a problem.

[0005] Further, since the antibacterial activity of a textile product treated with the above antibacterial agent is lost by washing, the present condition is to maintain the durability against washing by using a binder resin in combination.

[0006] The present invention has been made in view of such technical problems, and has as its object to provide a latent antibacterial agent. That is, an object of the present invention is to provide a latent antibacterial agent which has high safety before exhibiting antibacterial properties, has excellent antibacterial properties after manifesting antibacterial properties, and does not decrease in antibacterial properties even after washing.

Another object of the present invention is to provide a cellulosic product containing the latent antibacterial agent and an antibacterial cellulosic product.

[0008]

Means for Solving the Problems The present inventors have conducted intensive studies on the above-mentioned problems, and as a result, have found that a carboxyl group can be reduced to one.
The compound consisting of a polyol containing not less than one, a polyol containing no carboxyl group, and a polyisocyanate does not exhibit antibacterial properties by itself, nor does it exhibit antibacterial properties only by being contained in a cellulosic product. It has been found that antibacterial properties are exhibited by heating after containing.

Further, it has been found that an antibacterial cellulosic product containing this compound and heated exhibits excellent antibacterial properties and that the antibacterial properties do not decrease even after washing, thereby completing the present invention.

That is, the latent antibacterial agent for a cellulosic product according to the present invention comprises at least one carboxyl selected from the group consisting of tartaric acid, an alkylene oxide adduct of tartaric acid, and a compound represented by the following general formula (1): A polyol containing one or more groups,

Embedded image (Wherein R ¹ is a hydrogen atom or a carboxyl group, R ² and R
³ may be the same or different and each has 2 to 4 carbon atoms
One or more alkylene groups of R ² and R ³
Is a block copolymer chain or a random copolymer chain when m is two or more alkylene groups, m represents an integer of 0 to 8, and a and b each represent an integer of 0 to 100. A) polyether polyols, polyester polyols, and polyols containing no carboxyl group selected from the group consisting of polyols containing organopolysiloxanes; and aromatic polyisocyanates, aliphatic polyisocyanates, and alicyclic polyisocyanates. It is obtained by reacting with at least one polyisocyanate selected from the group consisting of: In the present invention, the polyol containing at least one carboxyl group is a polyol containing at least one carboxyl group selected from the group consisting of dimethylolpropionic acid, dimethylolbutanoic acid, and an alkylene oxide adduct thereof. Preferably, there is. Further, the present invention provides a method wherein the polyol containing no carboxyl group is polyethylene glycol, polypropylene glycol, polytetramethylene glycol, a compound represented by the following general formula (2), and a compound represented by the following general formula (3) And at least one carboxyl-free polyol selected from the group consisting of:

Embedded image (In the formula, R ⁴ is an alkylene group or alkenylene group having 2 to 18 carbon atoms, a cyclohexylene group, a phenylene group, or a naphthylene group, and R ⁵ and R ⁶ may be the same or different and each have 2 to 18 carbon atoms. One or two of the 6 alkylene groups
Or more, and when R ⁵ and R ⁶ are two or more alkylene groups, they may be block copolymer chains or random copolymer chains, n is an integer of 1 to 200, e and f
Represents an integer of 1 to 100, respectively.)

Embedded image (In the formula, R ⁷ and R ⁸ may be the same or different, each is one or more of alkylene groups having 2 to 4 carbon atoms, and R ⁷ and R ⁸ are two or more alkylene groups. In some cases, it may be a block copolymer chain or a random copolymer chain, p represents an integer of 10 to 150, and g and h each represent an integer of 1 to 100. It is preferably at least one polyisocyanate selected from the group consisting of hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, and isophorone diisocyanate.

The latent antibacterial treating agent for a cellulosic product according to the present invention comprises the above latent antibacterial agent for a cellulosic product as a main component.

Further, the cellulosic product according to the present invention comprises the above-mentioned latent antibacterial agent for cellulosic products contained in the cellulosic product.

[0013] Further, a method of expressing antibacterial properties of the present invention is characterized in that a fiber product containing the above-mentioned latent antibacterial agent for a cellulosic product is heated at an activation temperature of 120 to 190 ° C. A paper product containing a latent antibacterial agent for cellulosic products is heated at an activation temperature of 100 to 160C.

Further, the antibacterial fiber product of the present invention exhibits antibacterial properties by heating a fiber product containing the above-mentioned latent antibacterial agent for cellulosic products at an activation temperature of 120 to 190 ° C. It is characterized by. Further, the antibacterial paper product of the present invention is characterized in that the antibacterial property is exhibited by heating a paper product containing the above-mentioned latent antibacterial agent for a cellulosic product at an activation temperature of 100 to 160 ° C. I do.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION Preferred embodiments of the latent antibacterial agent of the present invention will be described in more detail.

The latent antibacterial agent for cellulosic products of the present invention is characterized by being obtained by reacting a polyol containing at least one carboxyl group, a polyol containing no carboxyl group, and a polyisocyanate.

Here, the cellulosic product refers to a product containing cellulose. Specifically, (1) natural fibers made of cotton, hemp, etc .; animal fibers (wool, silk, etc.), synthetic fibers (polyester, nylon, acrylic, polyurethane, etc.) and semi-synthetic fibers (rayon, acetate, etc.) Composite fibers of one or more types of fibers and cellulose fibers, and the like. These products may be in the form of yarn, fabric,
Knitted fabrics and non-woven fabrics (hereinafter, these are sometimes collectively referred to as “fiber products”), and (2) paper made of pulp, paper made of pulp mixed with synthetic fibers such as polyester, nylon, and acrylic (Hereinafter, these are sometimes collectively referred to as “paper products”). These cellulosic products include finishing agents, dyes, pigments, optical brighteners,
Conventionally used additives such as a sizing agent and a binder may be further contained.

The number of carboxyl groups in the polyol containing one or more carboxyl groups is not particularly limited, but is preferably 1 to 5. Further, the carboxyl group may be a metal salt such as sodium, potassium, calcium, zinc, copper, an ammonium salt, or an amine salt before and / or after the reaction.

The number of hydroxyl groups in the polyol containing one or more carboxyl groups is not particularly limited, but is preferably 2 to 5. An alkylene oxide such as ethylene oxide, propylene oxide or butylene oxide may be added to this hydroxyl group.

Preferred examples of the polyol containing one or more carboxyl groups include tartaric acid, an alkylene oxide adduct of tartaric acid, and a compound represented by the following general formula (1).

[0021]

Embedded image

(Wherein R ¹ is a hydrogen atom or a carboxyl group, R ² and R ³ may be the same or different, and each is one or more alkylene groups having 2 to 4 carbon atoms; ^{When 2} and R ³ are two or more alkylene groups, they may be block copolymer chains or random copolymer chains, m is an integer of 0 to 8, and a and b are each 0.
Represents an integer of ~ 100. Among the compounds represented by the general formula (1), dimethylolpropionic acid, dimethylolbutanoic acid and alkylene oxide adducts thereof are more preferably used.

The amount of the polyol containing at least one carboxyl group is not particularly limited, but is added so that the weight of the carboxyl group is at least 0.01% by weight based on the total weight of the latent antibacterial agent. Preferably.

As the polyol containing one or more carboxyl groups, only one kind may be used, or a mixture of two or more kinds may be used.

The number of hydroxyl groups of the polyol containing no carboxyl group is not limited, but is preferably 2 to 5.

Examples of polyols containing no carboxyl group include polyols such as polyether polyols, polyester polyols, polycarbonate diols, polybutadiene polyols, ethylene butylene diols, and polyols containing organopolysiloxanes. It is preferable to use a polyol containing a polyol, a polyester polyol, and an organopolysiloxane. Particularly, when a polyol containing a polyester polyol and / or an organopolysiloxane is used, the decrease in antibacterial properties after washing is very small.

Examples of the polyether polyol include polyethylene glycol, polypropylene glycol, polytetramethylene glycol and the like.

Examples of the polyester polyol include compounds represented by the following general formula (2).

[0029]

Embedded image

Where R^FourIs an alkylene having 2 to 18 carbon atoms
Group or alkenylene group, cyclohexylene group, phenyl
A ren group or a naphthylene group;^FiveAnd R⁶Is the same
May be different, each having an alkylene group having 2 to 6 carbon atoms
One or more kinds of ^FiveAnd R⁶Are two or more
When it is a alkylene group, it may be a block copolymer chain.
It may be a random copolymer chain, and n is an integer of 1 to 200.
The numbers, e and f each represent an integer of 1 to 100. ) As the polyol component of the polyester polyol,
Tylene glycol, propylene glycol, butanegio
Tools, hexanediol, polyethylene glycol,
Lipropylene glycol, polytetramethylene glycol
, Polyoxyethylene polyoxypropylene glycol
And the carboxylic acid component is terephthalate.
Luic acid, isophthalic acid, phthalic acid, naphthalenedicarboxylic
Acid, adipic acid, dodecanedicarboxylic acid, maleic acid,
Fumaric acid and the like. These polyol components and
Use one or two or more carboxylic acid components
Is also good.

Examples of the polyol containing an organopolysiloxane include compounds represented by the following general formula (3).

[0032]

Embedded image

(Wherein R ⁷ and R ⁸ may be the same or different and each is one or more alkylene groups having 2 to 4 carbon atoms, and R ⁷ and R ⁸ are two or more alkylene groups) When it is an alkylene group, it may be a block copolymer chain or a random copolymer chain, p is an integer of 10 to 150, g
And h each represent an integer of 1 to 100. The polyol containing the organopolysiloxane of the above general formula (3) can be prepared, for example, by adding allyl alcohol to methyl hydrogen polysiloxane using a platinum catalyst, and adding an alkylene oxide to the compound by a conventional method. It is obtained by adding.

The polyol containing no carboxyl group is 1
Only one type may be used, or a mixture of two or more types may be used.

The polyisocyanates include tolylene diisocyanate, diphenylmethane diisocyanate,
Xylylene diisocyanate, naphthalene diisocyanate, aromatic polyisocyanate such as polymeric MDI, hexamethylene diisocyanate, aliphatic polyisocyanate such as trimethylhexamethylene diisocyanate, dicyclohexylmethane diisocyanate,
Alicyclic polyisocyanates such as isophorone diisocyanate and cyclohexyl diisocyanate;

In order to prevent yellowing, it is preferable to use hexamethylene diisocyanate which is an aliphatic diisocyanate, dicyclohexylmethane diisocyanate which is an alicyclic diisocyanate, and isophorone diisocyanate.

Although only one type of polyisocyanate may be used, a mixture of two or more types may be used.

The reaction ratio of the polyol containing one or more carboxyl groups, the polyol containing no carboxyl group, and the polyisocyanate is not particularly limited.
If unreacted polyisocyanate remains after the reaction, gelation or yellowing may occur.
Assuming that the total number of hydroxyl equivalents of the polyol containing at least one and the polyol containing no carboxyl group is X, and the isocyanate equivalent number of the polyisocyanate is Y, Y / X ≦
It is preferably 1.

The method for synthesizing the latent antibacterial agent is not particularly limited, and reference is usually made to a known reaction method (eg, “Polyurethane Resin Handbook”, edited by Keiji Iwata, published by Nikkan Kogyo Shimbun, 1991). Can be preferably used. For example, the reaction can be performed in an organic solvent or without a solvent.

When an organic solvent is used, it is preferable to use an aprotic polar solvent. Examples of the aprotic polar solvent include dimethyl sulfoxide, dimethylformamide, dimethylacetamide and the like.

In order to promote the reaction, an organic tin compound such as diallyl stannous, tetraacyl stannic, dibutyltin diacetate, dibutyltin dilaurate, and a catalyst represented by triisobutylaluminum, tetrabutyltitanate and the like are used. You may.

The latent antibacterial treating agent for cellulosic products according to the present invention mainly comprises a latent antibacterial agent obtained by reacting a polyol containing at least one carboxyl group, a polyol containing no carboxyl group, and a polyisocyanate. Component.

The latent antibacterial treating agent for cellulosic products is
It may be liquid or solid at room temperature, but is preferably liquid. When the latent antibacterial agent is liquid, it may be used as a latent antibacterial treating agent for cellulosic products without adding other components. After dissolving in an organic solvent or dispersing in water, it may be used as a latent antibacterial treating agent for cellulosic products.

To disperse the latent antimicrobial agent in water,
When the latent antibacterial agent is a self-emulsifying type compound, it may be stirred in water without using an emulsifier, and when the latent antibacterial agent is a hardly water-soluble compound, it may be added with an emulsifying agent and stirred in water.

The cellulosic product according to the present invention is a cellulosic product containing a latent antimicrobial treating agent for cellulosic products.

The method for incorporating the latent antibacterial agent into the cellulosic product is not particularly limited, but a putting method, an immersion method, a coating method, a spray method, an internal addition method and the like are preferably used.

The content of the latent antibacterial agent in the cellulosic product is not particularly limited, and it is easy to appropriately select it according to the purpose of use. For example, the amount that can be used based on the weight of the cellulosic product is 0.001 to
Preferably it is in the range of 10% by weight.

After the latent antibacterial agent is contained in the cellulosic product, it is dried. The drying temperature is not particularly limited, but is preferably dried at a temperature lower than the activation temperature.

The method of expressing antibacterial properties according to the present invention is characterized in that a cellulosic product containing a latent antibacterial treating agent for cellulosic products is heated at an activation temperature.

The latent antibacterial treating agent for cellulosic products is
It does not show antimicrobial properties when it is contained in a cellulosic product and is dried at a temperature lower than the activation temperature, but exhibits antimicrobial properties when heated to the activation temperature.

The activation temperature of the fiber product among the cellulosic products is 120 to 190 ° C., preferably 130 to 160 ° C. The heating time is not particularly limited, but 1 to 10 minutes is a preferable range.

For paper products among the cellulosic products, the activation temperature is 100 to 160 ° C., preferably 105 to 150 ° C.

The antibacterial fiber product of the present invention comprises a fiber product containing the above-mentioned latent antibacterial agent for cellulosic products in an amount of 120.
It is characterized by exhibiting antibacterial properties by heating at an activation temperature of up to 190 ° C. Further, the antibacterial paper product of the present invention is characterized in that the antibacterial property is exhibited by heating a paper product containing the above-mentioned latent antibacterial agent for a cellulosic product at an activation temperature of 100 to 160 ° C. I do.

The antibacterial fiber products and antibacterial paper products obtained by heating at the activation temperature exhibit excellent antibacterial properties. Also, the antibacterial property does not decrease even after washing.

[0055]

EXAMPLES Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.

(Example 1) 0.85 mol of polypropylene glycol having a molecular weight of 2000, 0.85 mol of polytetramethylene glycol having a molecular weight of 1500, 0.2 mol of dimethylolbutanoic acid, and 1.8 mol of hexamethylene diisocyanate were added to an appropriate amount of dimethyl. Dissolved in formamide,
The reaction was carried out at 20 ° C. for 3 hours. After confirming that the unreacted isocyanate group had disappeared, the solvent was distilled off under reduced pressure, the temperature was cooled to 100 ° C. or less, and an emulsifier was added. Neutralized and emulsified by adding hot water. Finally, the concentration was adjusted to 15% by weight.

(Example 2) 0.4 mol of polypropylene glycol having a molecular weight of 2000, 1.0 mol of polytetramethylene glycol having a molecular weight of 1500, 0.5 mol of dimethylolbutanoic acid, and 1.8 of hexamethylene diisocyanate
Mol is dissolved in an appropriate amount of dimethylformamide.
For 3 hours. After confirming that unreacted isocyanate groups have disappeared, the solvent was distilled off under reduced pressure.
The mixture was cooled to 00 ° C. or lower, an emulsifier was added, carboxyl groups were neutralized with aqueous ammonia, and hot water was added to emulsify.
Finally, the concentration was adjusted to 15% by weight.

Example 3 0.5 mol of polypropylene glycol having a molecular weight of 2,000, 1.0 mol of polytetramethylene glycol having a molecular weight of 1500, and a polyalkylene glycol containing an organopolysiloxane having a molecular weight of 2,000 (BY16-201: Toray Dow) Corning Co., Ltd.) 0.2 mol, dimethylolbutanoic acid 0.2 mol,
1.8 mol of hexamethylene diisocyanate was dissolved in an appropriate amount of dimethylformamide and reacted at 120 ° C. for 3 hours. After confirming that unreacted isocyanate groups had disappeared, the solvent was distilled off under reduced pressure and the temperature was raised to 100 ° C. After cooling, an emulsifier was added, the carboxyl group was neutralized with aqueous ammonia, and emulsified by adding hot water. Finally, the concentration was adjusted to 15% by weight.

Example 4 Isophthalic acid / adipic acid /
1,6-hexanediol condensate (ADEKA NEW ACE F1212-29: manufactured by Asahi Denka Kogyo Co., Ltd.) 1.0 mol of polyester polyol having a molecular weight of 1756, dimethylolbutanoic acid 0.9 mol, hexamethylene diisocyanate 1.8 The mol was dissolved in an appropriate amount of dimethylformamide and reacted at 120 ° C. for 3 hours. After confirming that the unreacted isocyanate group had disappeared, the solvent was distilled off under reduced pressure, and the temperature was cooled to 100 ° C. or lower to obtain an emulsifier. Was added, and the carboxyl group was neutralized with ammonia water, and emulsified by adding hot water. Finally, the concentration was adjusted to 15% by weight.

Comparative Example 1 0.95 mol of polypropylene glycol having a molecular weight of 2,000, 0.95 mol of polytetramethylene glycol having a molecular weight of 1500, and 1.8 mol of hexamethylene diisocyanate were dissolved in an appropriate amount of dimethylformamide. The reaction was allowed to proceed for a period of time. After confirming that unreacted isocyanate groups had disappeared, the solvent was distilled off under reduced pressure, the temperature was cooled to 100 ° C. or lower, and emulsifier and hot water were added to emulsify. Finally, the concentration was adjusted to 15% by weight.

Comparative Example 2 15 of benzalkonium chloride
% Aqueous solution was prepared.

The antibacterial properties of the compounds obtained in Examples 1 to 4 and Comparative Examples 1 and 2 in an unheated state were evaluated based on Antibacterial Test Method 1. Table 1 shows the obtained results. In addition,
Table 1 also shows the results of the control without addition of the compound.

[0063]

[Table 1]

The compounds obtained in Examples 1 to 4 and Comparative Examples 1 and 2 were diluted to 5% by weight, and cotton broad cloth and polyester / cotton white cloth were treated with padding (1 dip / 1 nip). After drying for 1 minute, heat treatment was further performed at 160 ° C. for 3 minutes to obtain a test cloth. Washing this test cloth 1
The antibacterial activity based on the antibacterial activity test method 2 was evaluated for those washed and those not washed based on the test. In addition, whiteness based on the whiteness test method was evaluated for those not washed. Tables 2 and 3 show the obtained results. In addition,
Tables 2 and 3 also show the results of the untreated cloth as a control.

[0065]

[Table 2]

Regarding the viable cell count when evaluated after 50 washes, the number of viable cells treated in Example 3 or 4 was about one-tenth smaller than that of Examples 1 and 2 in each case. .

[0067]

[Table 3]

Regarding the number of viable bacteria when evaluated after 50 washes, those treated in Example 3 or 4 were about one-tenth smaller in any of the bacteria compared to Examples 1 and 2. .

Further, the compounds obtained in Examples 1 to 4 and Comparative Examples 1 and 2 were diluted to 1% by weight, the paper was padded (1 dip / 1 nip), dried at 105 ° C. for 3 minutes, and the test paper was dried. Obtained. Using this test paper, antibacterial test method 2
Was evaluated based on the antibacterial property based on the whiteness test method. Table 4 shows the obtained results. Table 4 also shows the results for unprocessed paper as a control.

[0070]

[Table 4]

The emulsion obtained in Example 1 was diluted to 3% by weight, and cotton broad cloth was padded (1 dip / 1 ni).
p) After the treatment, heat treatment 1 shown in Table 5 was performed, and then heat treatment 2 was performed as shown in Table 5 in the case of further heat treatment to obtain a test cloth. The antibacterial properties based on the antibacterial test method 2 were evaluated for the test cloth washed with the washing method 2 and the non-washed cloth. The results obtained are shown in Table 5.

[0072]

[Table 5]

(Test method) Antibacterial test method 1: A test solution was prepared by dissolving a compound to be tested in sterilized BHI broth so that the concentration of the compound to be tested was 2% by weight. Add 10 ⁵ cells / ml to 10 ml of this solution in advance.
0.1 ml of the prepared bacterial solution was added, and the increase or decrease in the number of bacteria after contacting for 18 hours was examined. As test bacteria, Staphylococcus aureus ATCC 6538P, Klebsiella pneumoniae (Kl
ebsiella pneumoniae ATCC 4352) and E. coli (Escheric
hia coli IFO 3301) was used.

Antibacterial Test Method 2: Antibacterial Test Method for Textile Products The test was conducted according to JIS L 1902: 1998. Staphylococcus (Staphylococcus)
aureus ATCC 6538P), Klebsiella pneumon
iae ATCC 4352) and Escherichia coli IFO 330
1) was used. The evaluation was performed according to the following criteria. ：: The viable cell count on the sample after 18 hours was 1 of the cell count immediately after contact.
/ 100 or less. Δ: The viable cell count on the sample after 18 hours is almost the same as the cell count immediately after contact. ×: The viable cell count on the sample after 18 hours is equal to or greater than the cell count immediately after contact.

Whiteness test method: Colorimeter CM-3 manufactured by Minolta
Hunter whiteness before washing was measured using 700d.
The larger the value, the less yellowing.

Washing method 1: Washing was carried out 50 times in accordance with the high-temperature accelerated washing method for bacteriostatically processed textile products (specific applications) specified by the Textile Product New Function Evaluation Council.

Washing method 2: Washing was performed 10 times in accordance with the method for sterilized processed fiber products (general use) specified by the Textile Product New Function Evaluation Council.

[0078]

As described above, the latent antibacterial agent of the present invention comprises a polyol containing one or more carboxyl groups,
It is obtained by reacting a polyol containing no carboxyl group with a polyisocyanate. Antibacterial properties are exhibited by incorporating such a latent antibacterial agent into a cellulosic product and heating at the activation temperature. In addition, antibacterial cellulosic products that contain such a latent antibacterial agent and exhibit antibacterial properties upon heating at an activation temperature do not decrease in antibacterial properties even after washing.

Continued on the front page (72) Inventor Yoshihiro Sasada 4-231-1, Bunkyo, Fukui City, Fukui Prefecture Inside Nika Chemical Co., Ltd. (72) Inventor Hidekazu Miyamoto 4-23-1, Bunkyo, Fukui City, Fukui Prefecture Nichika Chemical Co., Ltd. (56) References JP-A-8-157900 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) A01N 31/00-47/48

Claims (10)

(57) [Claims] 1. The method according to claim 1, wherein at least one carboxyl group selected from the group consisting of tartaric acid, an alkylene oxide adduct of tartaric acid, and a compound represented by the following general formula (1):
And a polyol containing at least one (Wherein R ¹ is a hydrogen atom or a carboxyl group, R ² and R
³ may be the same or different and each has 2 to 4 carbon atoms
One or more alkylene groups of R ² and R ³
Is a block copolymer chain or a random copolymer chain when m is two or more alkylene groups, m represents an integer of 0 to 8, and a and b each represent an integer of 0 to 100. A) polyether polyols, polyester polyols, and polyols containing no carboxyl group selected from the group consisting of polyols containing organopolysiloxanes; and aromatic polyisocyanates, aliphatic polyisocyanates, and alicyclic polyisocyanates. A latent antibacterial agent for cellulosic products, which is obtained by reacting at least one polyisocyanate selected from the group consisting of: 2. The polyol containing at least one carboxyl group selected from the group consisting of dimethylolpropionic acid, dimethylolbutanoic acid and alkylene oxide adduct thereof, wherein the polyol containing one or more carboxyl groups is The latent antibacterial agent for cellulosic products according to claim 1, wherein 3. The polyol containing no carboxyl group is selected from polyethylene glycol, polypropylene glycol, polytetramethylene glycol, a compound represented by the following general formula (2), and a compound represented by the following general formula (3). The latent antibacterial agent for a cellulosic product according to claim 1 or 2, which is a polyol containing no at least one carboxyl group selected from the group consisting of: Embedded image (In the formula, R ⁴ is an alkylene group or alkenylene group having 2 to 18 carbon atoms, a cyclohexylene group, a phenylene group, or a naphthylene group, and R ⁵ and R ⁶ may be the same or different and each have 2 to 18 carbon atoms. One or two of the 6 alkylene groups
Or more, and when R ⁵ and R ⁶ are two or more alkylene groups, they may be block copolymer chains or random copolymer chains, n is an integer of 1 to 200, e and f
Represents an integer of 1 to 100, respectively. (In the formula, R ⁷ and R ⁸ may be the same or different, each is one or more of alkylene groups having 2 to 4 carbon atoms, and R ⁷ and R ⁸ are two or more alkylene groups. In some cases, it may be a block copolymer chain or a random copolymer chain, p represents an integer of 10 to 150, and g and h each represent an integer of 1 to 100.) 4. The method according to claim 1, wherein the polyisocyanate is at least one polyisocyanate selected from the group consisting of hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, and isophorone diisocyanate. The latent antibacterial agent for a cellulosic product according to the above. 5. A latent antibacterial treating agent for cellulosic products, comprising the latent antibacterial agent for cellulosic products according to any one of claims 1 to 4 as a main component. 6. A cellulosic product containing the latent antibacterial agent for cellulosic products according to any one of claims 1 to 4. 7. A fibrous product containing the latent antibacterial agent for cellulosic products according to any one of claims 1 to 4,
A method of developing antibacterial properties by heating at an activation temperature of 20 to 190C. 8. A paper product containing the latent antibacterial agent for cellulosic products according to any one of claims 1-4.
A method of expressing antibacterial properties by heating at an activation temperature of 0 to 160 ° C. 9. A fiber product containing the latent antibacterial agent for a cellulosic product according to any one of claims 1-4.
An antibacterial fiber product that exhibits antibacterial properties when heated at an activation temperature of 20 to 190 ° C. 10. A paper product containing the latent antibacterial agent for a cellulosic product according to any one of claims 1-4.
An antibacterial paper product that exhibits antibacterial properties by heating at an activation temperature of 00 to 160 ° C.