ANTIBACTERIAL AND ANTIVIRAL COMPOSITION

Abstract

The present invention aims to provide an antibacterial and antiviral composition capable of exhibiting antibacterial and antiviral properties in a short period of time and excellent in handleability and safety. The present invention also aims to provide antibacterial and antiviral particles, a processed fabric, a coating material for a processed coating film, a processed coating film, a coating material for a UV-cured coating film, and a UV-cured coating film each prepared using the antibacterial and antiviral composition. Provided is an antibacterial and antiviral composition containing an antibacterial and antiviral polymer compound, the polymer compound being an amino group-containing polymer.

Claims

1. An antibacterial and antiviral composition comprising: a polymer compound having antibacterial and antiviral properties, the polymer compound being an amino group-containing polymer.

2. The antibacterial and antiviral composition according to claim 1, wherein the polymer compound has an amino group and a hydroxy group in the same molecule.

3. The antibacterial and antiviral composition according to claim 2, wherein the polymer compound is an amino group-containing polyvinyl alcohol.

4. The antibacterial and antiviral composition according to claim 1, further comprising a hydroxy group-containing polymer.

5. The antibacterial and antiviral composition according to claim 1, which has an antiviral activity value of 2 or higher.

6. Antibacterial and antiviral particles comprising the antibacterial and antiviral composition according to claim 1.

7. A processed fabric comprising the antibacterial and antiviral composition according to claim 1 on its surface.

8. A coating material for a processed coating film comprising the antibacterial and antiviral composition according to claim 1.

9. A processed coating film formed from the coating material for a processed coating film according to claim 8.

10. A coating material for a UV-cured coating film comprising: the antibacterial and antiviral composition according to claim 1; and a UV-curable resin.

11. A UV-cured coating film formed from the coating material for a UV-cured coating film according to claim 10.

Description

DESCRIPTION OF EMBODIMENTS The present invention is more specifically described in the following with reference to, but not limited to, examples.

EXAMPLE 1

[0084] An amount of 5 parts by weight of an amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s) was added to 95 parts by weight of an aerosol coating material (available from Tsuchiya Co., Ltd. under the trade name of Cosmocolor), and uniformly mixed to prepare an antibacterial and antiviral coating material. The aerosol coating material was a resin coating material containing an acrylic urethane resin, a plasticizer, and a pigment. The 4% by weight aqueous solution viscosity was measured at 20 C. in conformity with JIS K 6726.

[0085] The obtained antibacterial and antiviral coating material (20 g) was uniformly applied to a polypropylene plate (1 m.sup.2) and dried at room temperature for five hours to provide an antibacterial and antiviral molded body. A piece having a planar square shape (5.0 cm on each side) was cut out from the antibacterial and antiviral molded body, and was used as a test piece.

<Effective Amine Value Measuring Test>

[0086] To accurately weighed sample in an amount of 0.2 g was added 40 ml of DMSO, and the sample was dissolved therein on a hot plate at 70 C. for one hour. Then, the resulting solution was allowed to cool to ambient temperature, and 20 ml of ethanol was then added thereto. Thus, a measurement sample was prepared.

[0087] The effective amine value of the obtained measurement sample was measured by a method in conformity with JIS K 1557-7 using hexylamine as a reference material, and was 54.8 mgKOH/g. The measurement conditions are listed below.

[Measurement Conditions]

[0088] Equipment: Titrando (available from Metrohm) [0089] Dosing equipment: 800 Dosino+807 dosing unit (20ml) [0090] Electrode: Solvotrode (reference electrolyte: 0.4 mol/L [0091] TEABr in ethylene glycol) [0092] Titration solution: 0.1 mol/L perchloric acid solution in acetic acid [0093] Substance used for standardization of titration solution: KHP [0094] Titradion mode: DET U

EXAMPLE 2

[0095] An antibacterial and antiviral coating material, a molded body, and a test piece were obtained as in Example 1, except that the amino group-containing polyvinyl alcohol was changed to 5 parts by weight of a polyethylene polyamine resin (NEOFIX RP-70 available from Nicca Chemical Co., Ltd., active ingredient: 70%).

Comparative Example 1

[0096] An antibacterial and antiviral coating material, a molded body, and a test piece were obtained as in Example 1, except that the amino group-containing polyvinyl alcohol was changed to an unmodified polyvinyl alcohol (degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 7 mPa.Math.s).

Comparative Example 2

[0097] A molded article and a test piece were obtained as in Example 1, except that 20 g of an aerosol coating material (available from Tsuchiya Co., Ltd. under the trade name of Cosmocolor), instead of the antibacterial and antiviral coating material, was uniformly applied to a polypropylene plate (1 m.sup.2) and dried at room temperature for five hours.

<Evaluation 1>

[0098] The test pieces obtained in Examples 1 to 2 and Comparative Examples 1 to 2 were evaluated as described below. Table 1 shows the results.

(1) Test for Confirming Anti-Influenza Properties

(a) Preparation of Virus Solution

[0099] An influenza virus was inoculated to MDCK cells cultured in a 10-cm dish. After culturing at 34 C. for one hour, the culture supernatant (containing naive virus) was removed. To the 10-cm dish from which the supernatant had been removed was newly added an EMEM medium. After culturing at 34 C. for four days, the culture supernatant was collected to be centrifuged at a rotation speed of 800 rpm for five minutes. The supernatant resulting from the centrifugation was used as a virus solution.

(b) Measurement of Virus Reduction Rate

[0100] The virus solution diluted 10 times with an EMEM medium was dripped in an amount of 0.4 mL onto each of the test pieces obtained in the examples and comparative examples, and the resulting test piece was left to stand at room temperature for two hours. Then, the virus solution on the test piece was collected and mixed with an EMEM medium to be diluted 10 times, 100 times, 1,000 times, and 10,000 times. Each dilution was inoculated in an amount of 0.1 mL to MDCK cells sprinkled on a 96-well microplate, and cultured at 34 C. for one hour. After the culturing, the culture supernatant (containing naive virus) was removed, and an EMEM medium was added, followed by culturing at 34 C. for four days. After removal of the culture supernatant, the virus amount at which 50% of the cells were infected with the virus (Tissue Culture Infectious Dose 50 (TCID50)) was calculated based on the proportion of surviving cells, and the antiviral activity value and the virus reduction rate were obtained. The case where the virus reduction rate was 99.0% or higher was rated o (Good) and the case where the virus reduction rate was lower than 99.0% was rated x (Poor).

TABLE-US-00001 TABLE 1 Comparative Comparative Example 1 Example 2 Example 1 Example 2 Formulation Aerosol coating material 95 95 95 100 (parts by weight) Amino group-containing polyvinyl alcohol 5 0 0 0 Polyethylene polyamine resin (NEOFIX RP-70) 0 5 0 0 Unmodified polyvinyl alcohol 0 0 5 0 Test for confirming TCID50 2.3 2.3 5.3 5.3 anti-influenza Antiviral activity value 2 2 0 properties Reduction rate 99.0% 99.0% 0% Effect X

EXAMPLE 3

[0101] To a woven fabric made of polyester fiber was applied a 1.0% aqueous solution of an amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s, effective amine value: 54.8 mgKOH/g) to a weight per unit area of 1 g/m.sup.2, thereby preparing an antibacterial and antiviral fiber. A test piece (0.4 g) was cut out from the obtained antibacterial and antiviral fiber.

EXAMPLE 4

[0102] An antibacterial and antiviral fiber and a test piece were obtained as in Example 3, except that the weight per unit area was changed to 5 g/m.sup.2.

Comparative Example 3

[0103] A fiber and a test piece were obtained as in Example 3, except that the amino group-containing polyvinyl alcohol was changed to a 1.0% aqueous solution of an unmodified polyvinyl alcohol (degree of saponification: 99 mol %, 4% by weight aqueous solution viscosity: 7 mPa.Math.s).

Comparative Example 4

[0104] A test piece was prepared by cutting a woven fabric made of polyester fiber.

<Evaluation 2>

[0105] The test pieces obtained in Examples 3 to 4 and Comparative Examples 3 to 4 were evaluated as described below. Table 2 shows the results.

(2) Test for Confirming Anti-Norovirus Properties

(a) Preparation of Test Virus Suspension

[0106] CRFK cells (feline kidney-derived cells) were infected with feline calicivirus, cultured, and centrifuged to remove cellular debris. Thus, a virus suspension was prepared. The virus suspension was diluted 10 times with sterile distilled water to have a virus titer of 1 to 510.sup.7 PFU/mL. Thus, a test virus suspension was prepared.

(b) Measurement of Virus Infectivity Titer <Fabric>

[0107] (i) A virus suspension (feline calicivirus [F-9 ATCC VR-782]) was prepared.

[0108] (ii) The virus suspension (0.2 mL) was dripped onto each fabric test piece (0.4 g), and left to stand at 25 C. for two hours. The virus suspension after the reaction is called a virus stock solution.

[0109] (iii) To the virus stock solution was added 20 ml of a SCDLP medium (Soybean-Casein Digest Broth with Lecithin & Polysorbate 80), and vortex for five seconds was performed five times for washing out, thereby extracting 0.1 mL of a washed-out solution.

[0110] (iv) The extracted washed-out solution containing the virus stock solution was diluted with a maintenance medium to prepare a dilution series (10 times, 100 times, 1,000 times, 10,000 times, 100,000 times, 1,000,000 times).

[0111] (v) The prepared dilution series was inoculated into host cells (MDCK cells: derived from canine kidney cells), and the dilution ratio at which 50% of the cells were infected (tissue culture infective dose for 50% (TCID.sub.50)) was determined by the Behrens-Karber method. The viral infectivity titer V.sub.c of the virus stock solution was obtained by calculation.

[0112] (vi) The antiviral activity value Mv and the reduction rate (%) were obtained using the following equations in which V.sub.b represents the viral infectivity titer at 25 C. after two hours in Comparative Example 3. Antiviral activity value (Mv)=1g.sub.10(V.sub.b)1g.sub.10(V.sub.c) Reduction rate (%)=[(V.sub.bV.sub.c)100]/V.sub.b

[0113] With regard to the obtained virus reduction rates, the reduction rate of 99.99% or higher was rated oo (Excellent), the reduction rate of lower than 99.99% but not lower than 99.0% was rated o (Good), and the reduction rate of lower than 99.0% was rated x (Poor). Since the virus reduction in a short period of time is evaluated here, a high virus reduction rate can be considered to indicate immediate effectiveness.

TABLE-US-00002 TABLE 2 Comparative Comparative Example 3 Example 4 Example 3 Example 4 Weight per unit area Amino group-containing polyvinyl alcohol 1 5 (g/m.sup.2) Unmodified polyvinyl alcohol 1 Test for confirming Virus infiectivity titer 3.36 <2.30 7.13 7.13 anti-Norovirus Antiviral activity value 3.8 4.8 0 properties Reduction rate 99.98% 99.99% 0% Effect X

EXAMPLE 5

[0114] An amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s, effective amine value: 54.8 mgKOH/g) was added to purified water to prepare a 5% by weight sample solution.

EXAMPLE 6

[0115] A 10% by weight sample solution was prepared using the same amino group-containing polyvinyl alcohol as used in Example 5.

Comparative Example 5

[0116] An unmodified polyvinyl alcohol (degree of saponification: 99 mol %, 4% by weight aqueous solution viscosity: 7 mPa.Math.s) was added to purified water to prepare a 5% by weight sample solution.

Comparative Example 6

[0117] A 10% by weight sample solution was prepared using the same unmodified polyvinyl alcohol as used in Comparative Example 5.

Comparative Example 7

[0118] A liquid consisting only of purified water was used as a sample solution.

<Evaluation 3>

[0119] The sample solutions obtained in Examples 5 to 6 and Comparative Examples 5 to 7 were evaluated as described below. Table 3 shows the results.

(3) Viable Bacteria Count Test

(a) Preparation of Test Bacteria Solution

[0120] Test bacteria (Escherichia coli and Staphylococcus aureus) were cultured using a normal agar medium (Eiken Chemical Co., Ltd.) at 35 C. for 18 to 24 hours, and Escherichia coli was suspended in purified water and Staphylococcus aureus was suspended in saline. The numbers of bacteria were each adjusted to 10.sup.7 to 10.sup.8/mL. Thus, test bacteria solutions were prepared.

[0121] Escherichia coli used was Escherichia coli NBRC 3972 and Staphylococcus aureus used was Staphylococcus aureus subsp. aureus NBRC 12732.

(b) Counting of Viable Bacteria

[0122] The test bacteria solution (0.1 mL) was inoculated into the sample solution (10 mL) to provide a test solution. After storage at room temperature for 15 minutes, 1 hour, 6 hours, and 24 hours, the test solution was immediately diluted 1000 times or 100 times with an SCDLP medium (Nihon Pharmaceutical Co., Ltd.). Each dilution of the test solution was cultured at 35 C. for two days, and the number of viable bacteria in the test solution was counted using a medium for viable bacteria count.

[0123] In the cases where the number of viable bacteria is <100 and <1000, antibactreial properties are considered to be present.

TABLE-US-00003 TABLE 3 Comparative Comparative Comparative Example 5 Example 6 Example 5 Example 6 Example 7 Concentration of sample solution 5 wt % 10 wt % 5 wt % 10 wt % Escherichia coli Degree of dilution with 1000 times 1000 times 1000 times 1000 times 1000 times SCDLP medium Number At start <1000 <1000 7.8 10.sup.5 8.2 10.sup.5 8.0 10.sup.5 of viable 15 Minutes later <1000 <1000 * * * bacteria 1 Hour later <1000 <1000 7.6 10.sup.5 7.2 10.sup.5 8.9 10.sup.5 6 Hours later <1000 <1000 7.9 10.sup.5 7.2 10.sup.5 8.5 10.sup.5 24 Hours later <1000 <1000 7.5 10.sup.5 6.8 10.sup.5 5.2 10.sup.5 Staphylococcus Degree of dilution with 100 times 1000 times 100 times 100 times 100 times aureus SCDLP medium Number At start <100 <1000 6.2 10.sup.5 6.0 10.sup.5 5.5 10.sup.5 of viable 15 Minutes later <100 <1000 * * * bacteria 1 Hour later <100 <1000 6.5 10.sup.5 6.0 10.sup.5 6.2 10.sup.5 6 Hours later <100 <1000 6.3 10.sup.5 5.6 10.sup.5 5.2 10.sup.5 24 Hours later <100 <1000 5.6 10.sup.5 5.2 10.sup.5 5.8 10.sup.5 * Not measured

EXAMPLE 7

[Production of Polyvinyl Alcohol Powder]

[0124] A polyvinyl alcohol powder having an average particle size of 800 m formed of an amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s, effective amine value: 54.8 mgKOH/g) was obtained.

EXAMPLE 8

[Production of Polyvinyl Alcohol Powder]

[0125] A polyvinyl alcohol powder having an average particle size of 800 m formed of an amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s, effective amine value: 75.2 mgKOH/g) was obtained.

EXAMPLE 9

[Production of Polyvinyl Alcohol Powder]

[0126] A polyvinyl alcohol powder having an average particle size of 800 m formed of an amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s, effective amine value: 104.3 mgKOH/g) was obtained.

Comparative Example 8

[Production of Polyvinyl Alcohol Powder]

[0127] A polyvinyl alcohol powder having an average particle size of 800 m formed of a polyvinyl pyrrolidone (PVP)-containing polyvinyl alcohol (PVP-containing polyvinyl alcohol, degree of saponification: 99.0%, 4% by weight aqueous solution viscosity: 9.0 mPa.Math.s, polyvinyl pyrrolidone group content: 5 mol %) was obtained.

Comparative Example 9

[Production of Polyvinyl Alcohol Powder]

[0128] A polyvinyl alcohol powder having an average particle size of 800 m formed of a 2-acrylamido-2-methylpropane sulfonic acid (AMPS)-containing polyvinyl alcohol (AMPS-containing polyvinyl alcohol, degree of saponification: 99.0%, 4% by weight aqueous solution viscosity: 12.0 mPa.Math.s, 2-acrylamido-2-methylpropane sulfonic acid group content: 4 mol %) was obtained.

<Evaluation 4>

[0129] The polyvinyl alcohol powders obtained in Examples 7 to 9 and Comparative Examples 8 to 9 were evaluated as described below. Table 4 shows the results.

(4) Test for Determining Antiviral Properties of Powder

(a) pH Measurement of Powder Sample in Medium

[0130] For a solution containing 0.75 g of the obtained polyvinyl alcohol powder and 15 ml of a maintenance medium (EMEM), pH measurement was performed by the method defined in JIS 8802 (2011).

[0131] In the above pH measurement, the pH in the reaction between a virus suspension to be mentioned later and the polyvinyl alcohol powder was supposed to be determined.

[0132] The pH in the case where a virus suspension alone was added was also measured.

(b) Antiviral Property Test <Powder>

[0133] The antiviral property test of the powder was performed as in the (b) Measurement of viral infectivity <fabric> described above, except that the each fabric test piece (0.4 g) in the step (ii) was changed to powder sample (10 mg) and the amount of the SDCDLP medium in the step (iii) was changed from 20 ml to 10 ml. The antiviral activity value of 1.5 or higher was rated as o (Good) and the antiviral activity value of lower than 1.5 was rated as x (Poor).

TABLE-US-00004 TABLE 4 Comparative Comparative Addition of virus Example 7 Example 8 Example 9 Example 8 Example 9 suspension alone Amino group-containing polyvinyl alcohol 100 wt % (Effective amine value: 54.8 mgKOH/g) Amino group-containing polyvinyl alcohol 100 wt % (Effective amine value: 75.2 mgKOH/g) Amino group-containing polyvinyl alcohol 100 wt % (Effective amine value: 104.3 mgKOH/g) PVP-containing polyvinyl alcohol 100 wt % (PVP group content 5 mol %) AMPS-containing polyvinyl alcohol 100 wt % (AMPS group content: 4 mol %) Antiviral pH 9.3 9.7 9.9 7.5 7.4 7.7 property test Virus infectivity titer 3.9 2.0 2.8 5.4 5.4 5.4 Antiviral activity value 1.5 3.5 2.6 0.0 0.0 Evaluation x x

EXAMPLE 10

[Pulverization of Polyvinyl Alcohol Powder]

[0134] The polyvinyl alcohol powder (average particle size: about 800 m) produced in Example 9 was pulverized using a pulverizer (Wonder Crusher WC-3L) to prepare a polyvinyl alcohol powder having an average particle size of 140 m.

EXAMPLE 11

[Classification of Polyvinyl Alcohol Powder]

[0135] A polyvinyl alcohol powder having an average particle size of 65 m was obtained by passing the polyvinyl alcohol powder (average particle size: 140 m) produced in Example 10 through a sieve (200 mesh, aperture of 75 m).

EXAMPLE 12

[0136] A polyvinyl alcohol powder having an average particle size of 30 m was obtained by dissolving the polyvinyl alcohol powder produced in Example 9 in water and spray-drying the obtained aqueous solution for granulation.

<Evaluation 5>

[0137] The polyvinyl alcohol powders obtained in Examples 9 to 12 were evaluated as described below for confirming the immediate antiviral effectiveness. The safety of the polyvinyl alcohol powders obtained in Example 10 and other examples was evaluated by the following procedure. Table 5 shows the results.

(a) Antiviral Property Test (Confirmation of Immediate Effectiveness)

[0138] For determining the immediate effectiveness, evaluation was performed as in (b) Antiviral property test <powder>, except that the contact time between the virus and the sample was changed from two hours to 5 minutes or 10 minutes.

[0139] With regard to the obtained virus reduction rates, the case where the antiviral activity values in five-minute contact and in 10-minute contact were both 1.5 or higher was rated oo (Excellent). The case where the antiviral activity value in five-minute contact was lower than 1.5 but the antiviral activity value in 10-minute contact was 1.5 or higher was rated o (Good). The case where the antiviral activity value even in 10-minute contact was lower than 1.5 was rated x (Poor).

(b) Test for Confirming Safety

(i) Acute Oral Toxicity Test

[0140] An acute oral toxicity test (mouse) was performed on the polyvinyl alcohol powder obtained in Example 10 by a method in conformity with OECD guideline TG420 (fixed dose procedure). The polyvinyl alcohol powder was confirmed to have an LD.sub.50>2,000 mg/kg, ensuring the safety. The safety of the polyvinyl alcohol powders obtained in Examples 9, 11, and 12 was similarly confirmed.

(ii) Skin Irritation Test

[0141] A skin irritation test (epidermal cells) was performed on the polyvinyl alcohol powder obtained in Example 10 by a method in conformity with OECD guideline TG439 (in vitro). The polyvinyl alcohol powder was confirmed to be a non-irritant, ensuring the safety. The safety of the polyvinyl alcohol powders obtained in Examples 9, 11, and 12 was similarly confirmed.

TABLE-US-00005 TABLE 5 Addition of virus Example 9 Example 10 Example 11 Example 12 suspension alone Amino group- Effective amine value (mgKOH/g) 104.3 104.3 104.3 104.3 containing Average particle size (m) 800 140 65 30 polyvinyl alcohol Antiviral property Reaction time Item test 5 Minutes Virus infectivity titer 4.5 4.2 2.3 2.4 5.3 Antiviral activity titer 0.8 1.1 3.0 2.8 10 Minutes Virus infectivity titer 2.4 2.4 2.3 2.4 5.3 Antiviral activity titer 2.9 2.9 3.0 2.9 Evaluation

EXAMPLE 13

[Mixing of Unmodified Polyvinyl Alcohol Powder and Amino Group-Containing Polyvinyl Alcohol Powder]

[0142] A powder (average particle size: 100 m) of an unmodified polyvinyl alcohol (degree of saponification: 99 mol %, 4% by weight aqueous solution viscosity: 7 mPa.Math.s) and the amino group-containing polyvinyl alcohol powder produced in Example 12 were mixed at a ratio of 9:1 (parts by weight). Thus, a powder sample was prepared.

EXAMPLE 14

8 Mixing of Unmodified Polyvinyl Alcohol Powder and Amino Group-Containing Polyvinyl Alcohol Powder

[0143] A powder (average particle size: 100 m) of an unmodified polyvinyl alcohol (degree of saponification: 99 mol %, 4% by weight aqueous solution viscosity: 7 mPa.Math.s) and the amino group-containing polyvinyl alcohol powder produced in Example 12 were mixed at a ratio of 3:1 (parts by weight). Thus, a powder sample was prepared.

EXAMPLE 15

[Mixing of Unmodified Polyvinyl Alcohol Powder and Polyethyleneimine]

[0144] A powder (average particle size: 100 m) of an unmodified polyvinyl alcohol (degree of saponification: 99 mol %, 4% by weight aqueous solution viscosity: 7 mPa.Math.s) and polyethyleneimine (weight average molecular weight: 10,000, effective amine value: 1,008 mgKOH/g, available from Junsei Chemical Co., Ltd.) were mixed at a ratio of 3:7 (parts by weight) to prepare a sample.

EXAMPLE 16

[Mixing of Unmodified Polyvinyl Alcohol Powder and Polyethyleneimine]

[0145] An unmodified polyvinyl alcohol and polyethyleneimine were mixed as in Example 15, except that the mixing ratio was changed to 1:9 (parts by weight). The obtained mixture was used as a sample.

EXAMPLE 17

[Mixing of Cellulose Powder and Polyethyleneimine]

[0146] A commercially available cellulose powder (KC Flock W-400G available from Nippon Paper Industries Co., Ltd., average particle size of 24 m) and polyethyleneimine (weight average molecular weight: 10,000, effective amine value: 1,008 mgKOH/g, Junsei Chemical Co., Ltd.) were mixed at a ratio of 7:3 (parts by weight) to prepare a sample.

EXAMPLE 18

[Polyethyleneimine]

[0147] Polyethyleneimine (weight average molecular weight: 10,000, effective amine value: 1,008 mgKOH/g, Junsei Chemical Co., Ltd., 10 parts by weight) alone was used as a sample.

Comparative Example 10

[Unmodified Polyvinyl Alcohol Powder Alone]

[0148] An unmodified polyvinyl alcohol (degree of saponification: 99 mol %, 4% by weight aqueous solution viscosity: 7 mPa.Math.s, 10 parts by weight) alone was used as a powder sample (average particle size: 100 m).

Comparative Example 11

[Cellulose Powder Alone]

[0149] A cellulose powder (KC Flock W-400G available from Nippon Paper Industries Co., Ltd., average particle size of 24 m, 10 parts by weight) alone was used as a powder sample (average particle size: 24 m).

<Evaluation 6>

[0150] The samples obtained in Examples 13 to 18 and Comparative Examples 10 to 11 were evaluated as in (b) Antiviral property test <powder>. Table 6 shows the results. The antiviral activity value of 1.5 or higher was rated o (Good) and the antiviral activity value of lower than 1.5 was rated x (Poor).

TABLE-US-00006 TABLE 6 Example Example Example Example Example Example Comparative Comparative Addition of virus 13 14 15 16 17 18 Example 10 Example 11 suspension alone Mixed weight Amino group-containing 1 1 (parts by polyvinyl alcohol weight) Unmodified polyvinyl 9 3 3 1 10 alcohol Polyethyleneimine 7 9 3 10 Cellulose 7 10 Antiviral Virus infectivity titer 3.2 2.2 2.6 2.4 2.3 2.3 5.3 5.3 5.4 property Antiviral activity value 2.2 3.2 2.8 3.0 3.1 3.1 0.1 0.1 test Evaluation x x

EXAMPLE 19

[Preparation of Amino Group-Containing Polyvinyl Alcohol Aqueous Solution]

[0151] To 95 parts by weight of water was added 5 parts by weight of an amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s, effective amine value: 104.3 mgKOH/g), and they were heated at 80 C. for three hours so that the polyvinyl alcohol was dissolved. Thus, a 5% by weight aqueous solution of an amino group-containing polyvinyl alcohol was obtained.

(A-1) Production of Processed Fabric (Dipping)

[0152] In the obtained 5% by weight aqueous solution of an amino group-containing polyvinyl alcohol was immersed a polyester tropical cloth (polyester 100%, A4 size, weight per unit area of 120 g/m.sup.2). The cloth was then squeezed using a mangle at an interroll pressure of 3.0 kgf/cm.sup.2 (squeezing ratio of 79%, application amount: 95.2 g/m.sup.2), and dried at 120 C./10 minutes, thereby preparing a processed fabric.

(A-2) Production of Processed Fabric (Spraying)

[0153] The obtained 5% by weight aqueous solution of an amino group-containing polyvinyl alcohol was sprayed twice to a polyester tropical cloth (polyester 100%, A4 size, weight per unit area of 120 g/m.sup.2) by hand spraying (application amount: 96 g/m.sup.2) and then naturally dried (18 hours), thereby preparing a processed fabric.

(B-1) Production of Processed Coating Film (Aqueous Solution Coating)

[0154] The obtained 5% by weight aqueous solution of an amino group-containing polyvinyl alcohol was applied to a polyester film (polyester 100%, 7 cm15 cm, thickness of 0.1 mm, weight per unit area of 144 g/m.sup.2) using a bar coater. The application amount was 14 g/m.sup.2. Then, the film was dried at 60 C. for 30 minutes to prepare a processed coating film (aqueous solution coating).

(B-2) Production of Processed Coating Film (Aqueous Solution Spraying)

[0155] The obtained 5% by weight aqueous solution of an amino group-containing polyvinyl alcohol was sprayed twice to a polyester film (polyester 100%, 7 cm15 cm, thickness of 0.1 mm, weight per unit area of 144 g/m.sup.2) by hand spraying. The application amount was 16 g/m.sup.2. Then, the film was naturally dried (18 hours) to prepare a processed coating film (aqueous solution spraying).

[Production of Coating Material for UV Coating Film (5% by Weight Polyvinyl Alcohol)]

[0156] To 95 parts by weight of a UV-curable solventless acrylic resin was added 5 parts by weight of an amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s, effective amine value: 104.3 mgKOH/g), and they were mixed to prepare a coating material for a UV coating film (5% by weight polyvinyl alcohol).

[Production of Coating Material for UV Coating Film (10% by Weight Polyvinyl Alcohol)]

[0157] To 90 parts by weight of a UV-curable solventless acrylic resin was added 10 parts by weight of an amino group-containing polyvinyl alcohol (amino group-containing polyvinyl alcohol, degree of saponification: 99.0 mol %, 4% by weight aqueous solution viscosity: 6.0 mPa.Math.s, effective amine value: 104.3 mgKOH/g), and they were mixed to prepare a coating material for a UV coating film (10% by weight polyvinyl alcohol).

(C-1) Production of UV Coating Film (5% by Weight Polyvinyl Alcohol)

[0158] The obtained coating material for a UV coating film (5% by weight polyvinyl alcohol) was applied to a polyester film (polyester 100%, 7 cm15 cm, thickness of 0.1 mm, weight per unit area of 144 g/m.sup.2) using a bar coater. The application amount was 16 g/m.sup.2. Then, the coating film was irradiated with UV rays (512 mJ/cm.sup.2, 258 mW/cm.sup.2) for 10 seconds to be cured. Thus, a UV coating film (5% by weight polyvinyl alcohol) was obtained.

(C-2) Production of UV Coating Film (10% by Weight Polyvinyl Alcohol)

[0159] The obtained coating material for a UV coating film (10% by weight polyvinyl alcohol) was applied to a polyester film (polyester 100%, 7 cm15 cm, thickness of 0.1 mm, weight per unit area of 144 g/m.sup.2) using a bar coater. The application amount was 16 g/m.sup.2. Then, the film was irradiated with UV rays (512 mJ/cm.sup.2, 258 mW/cm.sup.2) for 10 seconds to be cured. Thus, a UV coating film (10% by weight polyvinyl alcohol) was obtained.

Comparative Example 12

[Preparation of Polyvinyl Alcohol Aqueous Solution]

[0160] To 95 parts by weight of water was added 5 parts by weight of an unmodified polyvinyl alcohol (degree of saponification: 99 mol %, 4% by weight aqueous solution viscosity: 7 mPa.Math.s), and they were heated at 80 C. for three hours so that the polyvinyl alcohol was dissolved. Thus, a 5% by weight polyvinyl alcohol aqueous solution was obtained.

[0161] Using the obtained 5% by weight polyvinyl alcohol aqueous solution, a processed fabric (dipping), a processed fabric (spraying), a processed coating film (aqueous solution coating), a processed coating film (aqueous solution spraying), and a UV coating film (5% by weight polyvinyl alcohol) were obtained as in (A-1), (A-2), (B-1), (B-2), and (C-1) in Example 19.

<Evaluation 7>

Antiviral Property Test

[0162] An antiviral property test as in (4) Antiviral property test was performed on the processed fabrics (dipping), processed fabrics (spraying), processed coating films (aqueous solution coating), processed coating films (aqueous solution spraying), UV coating films (5% by weight polyvinyl alcohol), and UV coating film (10% by weight polyvinyl alcohol) obtained in Example 19 and Comparative Example 12. The antiviral activity value of 1.5 or higher was rated o (Good) and the antiviral activity value of lower than 1.5 was rated x (Poor).

(Procedure for Testing Processed Fabric)

[0163] With regard to the processed fabric, the test was performed as in (4) Antiviral property test described above, except that 10 mg of powder sample was changed to 0.4 g of processed fabric sample in the step (ii). In addition, in the step (iii), the amount of the SCDLP medium was changed from 10 ml to 20 ml.

(Procedure for Testing Processed Coating Film and UV Coating Film)

[0164] With regard to the processed coating film and UV coating film, the test was performed as in (4) Antiviral property test described above, except that the steps (ii) and (iii) were changed as follows.

[0165] (ii) A coating film sample (5 cm5 cm) was secured on the bottom face of a Petri dish (9020) with double-sided tape, and 0.4 mL of the virus suspension was dripped to the center. The sample was slowly covered with a polyester film (4 cm4 cm), and left to stand at 25 C. for 24 hours. With an aim of preventing drying of the virus suspension, a kimwipe impregnated with 1 ml of sterilized water was secured on the lid of the Petri dish.

[0166] (iii) Then, 10 ml of the SCDLP medium was added to the Petri dish, and the Petri dish was shaken for washing out, thereby extracting 0.1 ml of a washed-out solution.

TABLE-US-00007 TABLE 7 Antiviral property test Application Virus Antiviral Polyvinyl alcohol amount infectivity activity Form Type (g/m.sup.2) titer value Evaluation Example 19 (A-1) Processed fabric Amino group- 95.2 4.2 3.9 (Dipping) containing polyvinyl alcohol (A-2) Processed fabric Amino group- 96 4.6 3.5 (Spraying) containing polyvinyl alcohol (B-1) Processed coating film Amino group- 14 2.0 4.5 (Aqueous solution coating) containing polyvinyl alcohol (B-2) Processed coating film Amino group- 16 3.2 3.3 (Aqueous solution spraying) containing polyvinyl alcohol (C-1) UV coating film Amino group- 16 2.5 4.0 (5 wt % PVA) containing polyvinyl alcohol (C-2) UV coating film Amino group- 16 2.0 4.5 (10 wt % PVA) containing polyvinyl alcohol Comparative (A-1) Processed fabric Unmodified 95.2 7.5 0.6 x Example 12 (Dipping) polyvinyl alcohol (A-2) Processed fabric Unmodified 96 7.5 0.6 x (Spraying) polyvinyl alcohol (B-1) Processed coating film Unmodified 14 6.2 0.3 x (Aqueous solution coating) polyvinyl alcohol (B-2) Processed coating film Unmodified 16 5.9 0.6 x (Aqueous solution spraying) polyvinyl alcohol (C-1) UV coating film Unmodified 16 6.2 0.3 x (5 wt % PVA) polyvinyl alcohol

INDUSTRIAL APPLICABILITY

[0167] The present invention can provide an antibacterial and antiviral composition capable of exhibiting antibacterial and antiviral properties in a short period of time and excellent in handleability and safety. The present invention can also provide antibacterial and antiviral particles, a processed fabric, a coating material for a processed coating film, a processed coating film, a coating material for a UV-cured coating film, and a UV-cured coating film each prepared using the antibacterial and antiviral composition.