Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P3/00—Fungicides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule

Definitions

• the present invention relates to a microbial adhesion inhibiting resin and an antibacterial and antiviral treated product.
• the COVID-19 pandemic has led to increased interest in antibacterial and antiviral agents and processed products.
• antibacterial and antiviral agents and processed products that prevent infection in patients with weakened resistance in medical and nursing care facilities were the norm, but with the spread of COVID-19, they have become more widely used in ordinary homes, public transportation, commercial facilities, companies, and factories.
• Most current antibacterial and antiviral processed products inactivate bacteria and viruses by damaging them, but the inactivated bacteria and viruses remain on the product surface. If more bacteria or viruses adhere to the inactivated bacteria or viruses, they will not come into contact with the antibacterial and antiviral processed surface, so they will remain active and grow, forming a biofilm that cannot be controlled by drugs.
• Polymers having phosphorylcholine groups that are used in conventional technology have low protein adsorption properties (e.g., Patent Document 1, etc.), and also have the effect of reducing microbial adhesion (e.g., Patent Document 2, etc.).
• the polymers having phosphorylcholine groups disclosed in Patent Documents 1 and 2 have ionic groups (cations and anions), which may impair the ability to inhibit adhesion of microorganisms.
• the present invention has been made to solve the above problems, and aims to provide a microbial adhesion inhibitory resin and an antibacterial and antiviral processed product that have the same or better microbial adhesion inhibitory properties as conventional polymers having ionic groups such as phosphorylcholine groups, even when a nonionic copolymer is used.
• the microbial adhesion inhibitory resin and antibacterial and antiviral processed product of the present invention are nonionic, they are expected to have stable microbial adhesion inhibitory properties without being affected by pH or salt concentration.
• a microbial adhesion inhibitory resin comprising a block copolymer composed of a polymer (A) of a monomer containing a monomer (a) represented by the following general formula (1) and a polymer (B) of a monomer containing one or more monomers selected from the group consisting of monomers (b) represented by the following general formulas (2) to (7).
• R 0 is an alkyl group having 1 to 3 carbon atoms
• R 1 is a hydrogen atom or a methyl group
• R 2 and R 7 are each independently an alkylene group having 2 to 3 carbon atoms
• R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or an alkyl group having 1 to 2 carbon atoms
• X is a monovalent anion selected from -CO 2 - , -SO 3 - , -OSO 3 - , -OSO 2 - , -OP( ⁇ O)(OR 8 )O - , -OP( ⁇ O)(R 8 )O - , -P( ⁇ O)(OR 8 )O - and -P( ⁇ O)(R 8 )O -
• R 8 is an alkyl group having 1 to 3 carbon atoms
• n is an integer from 1 to 9.
• the polymerization degree of the polymer (A) is 30 to 3,000
• the polymerization degree of the polymer (B) is 20 to 20,000.
• the microbial adhesion inhibitory resin according to any one of [1] to [3].
• the present invention even when a non-ionic copolymer is used, it is possible to provide a microbial adhesion-inhibiting resin that has the same or better microbial adhesion-inhibiting properties as conventional polymers having ionic groups such as phosphorylcholine groups, and antibacterial and antiviral processed products coated with the microbial adhesion-inhibiting resin. Furthermore, because the microbial adhesion-inhibiting resin of the present invention is non-ionic, it is possible to provide a microbial adhesion-inhibiting resin that has stable microbial adhesion-inhibiting properties without being affected by pH or salt concentration, and antibacterial and antiviral processed products coated with the microbial adhesion-inhibiting resin.
• 1 is a SEM photograph showing the number of bacteria adhering to a surface in the microbial adhesion inhibition test of Example 1-1.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Example 1-2.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Example 1-3.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Example 1-4.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Example 1-5.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Example 1-6.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Example 1-7.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Comparative Example 1-1.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Comparative Example 1-2.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Comparative Example 1-3.
• Example 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Example 1-8.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Comparative Example 1-4.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Example 1-9.
• 1 is a SEM photograph showing the number of bacteria adhering to the surface in the microbial adhesion inhibition test of Comparative Example 1-5.
• ⁇ means greater than or equal to the value before “ ⁇ ” and less than or equal to the value after " ⁇ ”.
• (Meth)acrylic is a general term for acrylic and methacrylic
• (meth)acrylate compound (B) is a general term for acrylate compounds and methacrylate compounds.
• (Meth)acrylic acid is a general term for acrylic acid and methacrylic acid.
• the microbial adhesion-inhibiting resin of one embodiment of the present invention (sometimes referred to as the microbial adhesion-inhibiting resin of the present embodiment) is a polymer of monomers including the monomer (a) represented by the above general formula (1).
• the polymer (A) and the polymer (B) are preferably in a molar ratio (A:B) of 1:50 to 50:1.
• the monomer (a) used in the present invention the monomer (a) represented by the above general formula (1) is used.
• R 0 is an alkyl group having 1 to 3 carbon atoms
• R 1 is a hydrogen atom or a methyl group
• R 2 is an alkylene group having 2 to 3 carbon atoms.
• monomer (a) improves the film-forming ability of the copolymer and adhesion to the substrate, allowing for a wide range of control over the thickness of the coating film, resulting in a smoother coating film.
• the surface of the coating film has the ability to inhibit the adhesion of microorganisms.
• the polymer (A) in the present invention is a polymer obtained by polymerizing only the monomer (a).
• Monomers that can be used other than monomer (a) include monomers represented by the following formulas (2) to (7) and (meth)acrylic monomers having functional groups such as hydroxyl groups, glycidyl groups, isocyanato groups, carboxyl groups, amino groups, and sulfonic acid groups.
• the monomer (b) used in the present invention is (meth)acrylamide and/or its derivatives (N- or N,N-substituted (meth)acrylamide). It is particularly preferable to use the acrylamide monomers of the above formulas (2) to (7).
• R 1 is a hydrogen atom or a methyl group
• R 2 and R 7 are each independently an alkylene group having 2 to 3 carbon atoms
• R 3 , R 4 , R 5 , and R 6 are each independently a hydrogen atom or an alkyl group having 1 to 2 carbon atoms
• R 8 is an alkyl group having 1 to 3 carbon atoms
• n is an integer from 1 to 9.
• the resulting block copolymer has good solubility or dispersibility in water and high stability, and the copolymer has good film-forming ability, resulting in a smoother coating film. Furthermore, when N,N-dimethylacrylamide is used as monomer (b), the resulting coating film surface is particularly excellent at inhibiting the adhesion of microorganisms, making it suitable for antibacterial and antiviral processed products.
• the polymer (B) is a polymer containing the monomer (b), and the polymer (B) is a polymer consisting of the monomer (b) represented by the above general formulas (2) to (7), or includes a copolymer with another monomer.
• the monomer (a) is preferably used as the other monomer used in the copolymer.
• the ratio (molar ratio) of the monomer (b):monomer (a) is 99:1 to 10:90, more preferably 95:5 to 30:70, even more preferably 90:10 to 50:50, and particularly preferably 90:10 to 60:40.
• the copolymer consisting of the monomer (b) and the monomer (a) also has the characteristic that a block copolymer can be more easily synthesized.
• copolymerizable monomers can be used in combination in the polymer (B) or copolymer (B) as necessary. This is to adjust the balance of hydrophilicity/hydrophobicity of the block copolymer, or to impart functional groups to further suppress interaction with proteins.
• acrylic monomers having an anionic group such as a sulfonic acid group or a carboxyl group acrylic monomers having a cationic group such as a quaternary ammonium group, acrylic monomers having an amphoteric ionic group having a quaternary ammonium group and a phosphate group, acrylic monomers having an amino acid residue having a carboxyl group and an amino group, acrylic monomers having a sugar residue, acrylic monomers having a hydroxyl group, acrylic monomers having polyethylene glycol or polypropylene glycol chains, amphiphilic acrylic monomers having both a hydrophilic chain such as polyethylene glycol and a hydrophobic group such as a nonylphenyl group, polyethylene glycol diacrylate, N,N'-methylenebisacrylamide, etc. can be used in combination.
• an anionic group such as a sulfonic acid group or a carboxyl group
• acrylic monomers having a cationic group such as a quaternary ammonium group
• the molar ratio (A:B) of the polymer (A) to the polymer (B) may be 1:50 to 50:1.
• the block copolymer may be a triblock type copolymer, a diblock type copolymer, or a multi-branched type block copolymer.
• the arrangement of the polymers (A) and (B) is not necessarily limited as long as it exhibits the above-mentioned properties, and for example, A-B type, A-B-A type, B-A-B type, and [B-A] p (p is the branching number of B, which is 3 to 10) are preferably used.
• A-B type, A-B-A type, and [B-A] p multi-branched type are more preferred, and A-B type and A-B-A type are most preferred.
• the [B-A] p multi-branched type referred to here refers to the one shown in the following structural example.
• the molar ratio (A:B) of component A to component B in the block copolymer according to this embodiment is preferably in the range of 1:60 to 60:1, more preferably in the range of 1:20 to 20:1, and most preferably in the range of 1:20 to 1:1.
• the resulting block copolymer has good solubility or dispersibility in water and high stability, the copolymer has good film-forming ability, and a smoother coating film is obtained.
• the coating film surface has the ability to inhibit microbial adhesion, which is preferable.
• the degree of polymerization of A is preferably in the range of 30 to 3000 and the degree of polymerization of B is preferably in the range of 20 to 20000, more preferably in the range of 100 to 1000 and the degree of polymerization of B is 100 to 5000, and particularly preferably in the range of 100 to 500 and the degree of polymerization of B is 200 to 2000.
• the resulting block copolymer has good solubility or dispersibility in water, making it easy to prepare an aqueous paint, and also has good film-forming ability and inhibits microbial adhesion on the surface of the resulting coating film, which is preferable.
• the block copolymer according to the present embodiment is not particularly limited in the manufacturing method as long as the monomers (a) and (b) are polymerized to synthesize a block copolymer consisting of a polymer (A) and a polymer (B).
• the following first and second methods can be mentioned as known and commonly used polymerization methods.
• the first method is a method in which, in the presence of a chain transfer agent (hereinafter referred to as a RAFT agent) such as trithiocarbonate, an azo compound and/or an organic peroxide is used as a radical polymerization initiator to first subject the monomer (a) to living radical polymerization, and the resulting polymer (A) is then subjected to living radical polymerization of the monomer (b).
• a RAFT agent chain transfer agent
• an azo compound and/or an organic peroxide is used as a radical polymerization initiator to first subject the monomer (a) to living radical polymerization, and the resulting polymer (A) is then subjected to living radical polymerization of the monomer (b).
• the second method is a synthesis method of a block copolymer in which, in the presence of an organic halide and a transition metal complex, the monomer (b) is radically polymerized, and then the monomer (a) is added and radically polymerized
• a method for synthesizing the block copolymer according to this embodiment the following methods (1-1) to (2-2) among known living radical polymerization methods are preferable.
• (1-1) In the first method, a RAFT agent and a monomer (a) are first polymerized in the presence of a small amount of a polymerization initiator, and then a macro RAFT agent consisting of only a polymer (A) is synthesized by isolating and purifying the polymer, and then the macro RAFT agent and a monomer (b) are polymerized in the presence of a small amount of a polymerization initiator to obtain a block copolymer.
• (1-2) In the second method, first, monomer (b) is polymerized in the presence of an organic halide and a transition metal complex, and then the polymer is isolated and purified to synthesize a polymer end halide consisting of only polymer (B), and then monomer (a) is polymerized with the polymer end halide in the presence of a transition metal complex to obtain a block copolymer.
• the RAFT agent and the monomer (a) are polymerized in the presence of a small amount of a polymerization initiator, and then, without isolating the polymer, the monomer (b) is added to obtain a block copolymer.
• the monomer (b) is polymerized in the presence of an organic halide and a transition metal complex, and then the monomer (a) is added without isolating the polymer to obtain a block copolymer.
• the methods (2-1) and (2-2) it is not necessary to wait until the first monomer is completely consumed before adding the next monomer, but the next monomer may be added when the conversion rate of the first monomer reaches about 65% or more.
• the polymer obtained in this case is not a complete block copolymer, but a so-called tapered block copolymer in which monomer (a) and monomer (b) are partially mixed. However, if the ratio of monomer (a) to monomer (b) is appropriately selected, a copolymer having the same functions as a complete block copolymer can be obtained.
• polymer (B) is a copolymer of monomer (a) and monomer (b)
• a method of polymerizing a mixture of monomer (a) and monomer (b) can be used.
• the solvent used in the polymer solution containing the microbial adhesion inhibitory resin is water, an organic solvent, or a mixture thereof.
• the type and concentration of the solvent used vary depending on the composition and molecular weight of the resulting block copolymer and the type and surface properties of the substrate to be coated. More preferably, a solvent having a solvent concentration of 99.95 to 90% by mass is used, which is mainly composed of ethanol, methanol, or isopropanol, which has excellent volatility and low invasiveness to the substrate.
• the microbial adhesion inhibitory resin of the present invention when used as an aqueous solution, it is desirable to use a surfactant in combination with the resin, or to subject the surface of the substrate to a hydrophilic treatment such as ultraviolet/ozone treatment, corona treatment, or plasma treatment in order to improve adhesion to the substrate.
• a surfactant in combination with the resin, or to subject the surface of the substrate to a hydrophilic treatment such as ultraviolet/ozone treatment, corona treatment, or plasma treatment in order to improve adhesion to the substrate.
• An antibacterial and antiviral processed product according to one embodiment of the present invention is a product coated with the microbial adhesion-inhibiting resin according to this embodiment.
• the products to be subjected to the antibacterial and antiviral treatment include medical tools, nursing care tools, etc.
• the medical tools include catheters, tubes, wound dressings, contact lenses, artificial respiration masks, and injection needles.
• examples of the products to be treated with the antibacterial and antiviral agent include tools and devices that many users touch in homes, public transportation, commercial facilities, companies, and factories.
• examples include tables, chairs, doorknobs, handrails, switches, bathtubs, faucets, toilets, washbasins, kitchens, and water purification filters.
• examples include handrails, hanging straps, and chairs.
• examples of products that can be subjected to the antibacterial and antiviral treatment include general consumer goods such as food packages, beverage containers, tableware, and clothing.
• the product to be antibacterial and antiviral processed according to this embodiment has the feature that a wide variety of materials can be used as the material for the surface to be coated with the microbial adhesion inhibitory resin.
• materials such as glass, ceramics, and metals are also preferably used.
• a uniform coating film can be produced on a substrate of any shape or form, such as a plate, sheet, straw, fiber, sphere, nonwoven fabric, or porous material.
• materials such as glass and metals are also preferably used.
• a coating film can be produced on a substrate of any shape or form, such as a plate, sheet, straw, thread, or sphere.
• the antibacterial and antiviral processed product of this embodiment may have adhesion inhibitory properties against microorganisms including bacteria and viruses.
• bacteria include gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae, and gram-positive bacteria such as Staphylococcus aureus, Bacillus subtilis, and methicillin-resistant Staphylococcus aureus.
• viruses include enveloped influenza viruses, coronaviruses, non-enveloped noroviruses, and adenoviruses.
• the mixture was dissolved in tetrahydrofuran, and the contents of monomer (a) and monomer (b) were measured by gas chromatography (GC; Agilent Technologies 7890B GC system) equipped with a Phenomenex ZB-WAX column (length 30 m, inner diameter 0.25 mm, film thickness 0.25 ⁇ m).
• GC gas chromatography
• Phenomenex ZB-WAX column length 30 m, inner diameter 0.25 mm, film thickness 0.25 ⁇ m.
• the conversion rates of each were calculated from the results, and the conversion rate of monomer (a) was 100%, and the conversion rate of monomer (b) was 99%.
• the structure of block copolymer P1 was identified as shown by the following formula (9).
• the mixed solution of the AB block copolymer P2 of the present invention was subjected to GC measurement in the same manner as in Synthesis Example 1. As a result, the conversion rate of the monomer (a) was 100% and the conversion rate of the monomer (b) was 99%.
• the structure of the block copolymer P2 was identified as shown by the following formula (10). The results of the GPC measurement are shown in Table 1.
• the mixed solution of the AB type block copolymer P3 of the present invention was subjected to GC measurement in the same manner as in Synthesis Example 1. As a result, the conversion rate of the monomer (a) was 100%, and the conversion rate of the monomer (c) was 98%.
• the structure of the block copolymer P3 was identified as shown by the following formula (11). The results of GPC measurement are shown in Table 1.
• the mixed solution of the AB block copolymer P4 of the present invention was subjected to GC measurement in the same manner as in Synthesis Example 1.
• the conversion of monomer (a) was 100% and the conversion of monomer (d) was 84%.
• the structure of block copolymer P4 was identified as shown by the following formula (12).
• the results of GPC measurement are shown in Table 1.
• the mixed solution of the AB block copolymer P5 of the present invention was subjected to GC measurement in the same manner as in Synthesis Example 1, and the conversion of the monomer (e) was 85% and the conversion of the monomer (b) was 95%.
• the structure of the block copolymer P5 was identified as shown by the following formula (13). The results of the GPC measurement are shown in Table 1.
• the mixed solution of the ABA block copolymer 6 of the present invention was subjected to GC measurement in the same manner as in Synthesis Example 1, and the conversion rate of monomer (a) was 100%, and the conversion rate of monomer (b) was 99%.
• the structure of block copolymer P6 was identified as shown in the following formula (15). The results of GPC measurement are shown in Table 1.
• the theoretical molecular weights of polymer (A), polymer (B) and block copolymer were calculated from the above conversion rate using the following formula.
• the theoretical molecular weight Mn of polymer (A) was approximately 32,500 (250 mol)
• the theoretical molecular weight Mn of polymer (B) was approximately 148,000 (1,480 mol)
• the theoretical molecular weight Mn of block copolymer P1 was approximately 213,000.
• Example 1-1 [Preparation of coating film of microbial adhesion inhibitory resin]
• the block copolymer P1 obtained in Synthesis Example 1 above was dissolved in ethanol to obtain a polymer solution L1 having a coating concentration of 0.5% by mass as the microbial adhesion-inhibiting resin of the present invention.
• the polymer solution L1 was then thinly coated on a PEN (polyethylene naphthalate) film whose surface had been treated with ultraviolet light and ozone, and then dried to obtain a PEN film F1 having a microbial adhesion-inhibiting resin coating.
• PEN polyethylene naphthalate
• the number of bacteria was counted in the image observed at 1500 times, and the number of attached bacteria was calculated as the average of two fields of view (two images). The results are shown in Table 2.
• the glutaraldehyde solution was prepared by adjusting the concentration of glutaraldehyde (Kanto Chemical, glutaraldehyde solution, 25%, for electron microscopes) to 1% with phosphate buffered saline (Fujifilm Wako Pure Chemical Industries, D-PBS(-)).
• PEN films F2 to F6 having microbial adhesion-inhibiting resin coatings were obtained in the same manner as in Example 1-1, except that the block copolymers P2 to P6 were used.
• the microbial adhesion-inhibiting properties of the PEN films F2 to F6 were evaluated in the same manner as in Example 1-1. The results are shown in Figures 2 to 6 and Table 2.
• Example 7 A PEN film F7 having a microbial adhesion-inhibiting resin coating was obtained in the same manner as in Example 1-1, except that the polymer solution L2 having a coating concentration of 0.1% by mass of the block copolymer P6 was used. A microbial adhesion-inhibiting test of the PEN film F7 was then carried out in the same manner as in Example 1-1. The results are shown in FIG. 7 and Table 2.
• Example 1-1 A PEN film cF1 having a microbial adhesion-inhibiting resin coating was obtained in the same manner as in Example 1-1, except that the polymer cP1 obtained in Comparative Synthesis Example 1 was used. A microbial adhesion-inhibiting test of the PEN film cF1 was then carried out in the same manner as in Example 1-1. The results are shown in FIG. 8 and Table 2.
• Example 1-2 A PEN film cF2 having a microbial adhesion-inhibiting resin coating was obtained in the same manner as in Example 1-7, except that the polymer cP1 obtained in Comparative Synthesis Example 1 was used. A microbial adhesion-inhibiting test of the PEN film cF2 was then carried out in the same manner as in Example 1-1. The results are shown in FIG. 9 and Table 2.
• Example 1-3 A PEN film cF3 not having a microbial adhesion-inhibiting resin coating was obtained in the same manner as in Example 1-1, except that ethanol not containing a polymer was used instead of the polymer solution L1. A microbial adhesion evaluation test of the PEN film cF3 was then carried out in the same manner as in Example 1-1. The results are shown in FIG. 10 and Table 2.
• Examples 1 to 8 A test for evaluating the microbial adhesion inhibitory properties of PEN film F6 was carried out in the same manner as in Example 1-6, except that the LB medium (pH 7) in Example 1-6 was adjusted to pH 5 by adding 1N-HCl (Kanto Chemical). The results are shown in FIG. 11 and Table 3.
• Comparative Examples 1 to 4 A test for evaluating the microbial adhesion inhibitory properties of the PEN film cF1 was carried out in the same manner as in Example 1-1, except that the LB medium (pH 7) of Comparative Example 1-1 was adjusted to pH 5 by adding 1N-HCl (Kanto Chemical). The results are shown in FIG. 12 and Table 3.
• Examples 1 to 9 A test for evaluating the microbial adhesion inhibitory effect of PEN film F6 was carried out in the same manner as in Example 1-6, except that NaCl was added to the LB medium (NaCl concentration: 1% by mass) in Example 1-6 to adjust the NaCl concentration to 2% by mass. The results are shown in FIG. 13 and Table 4.
• Comparative Example 1-5 A test for evaluating the microbial adhesion inhibitory properties of the PEN film cF1 was carried out in the same manner as in Example 1-1, except that NaCl was added to the LB medium (NaCl concentration: 1% by mass) of Comparative Example 1-1 to adjust the NaCl concentration to 2% by mass. The results are shown in FIG. 14 and Table 4.
• Examples 2-1, 2-2, Comparative Examples 2-1 to 2-3 The microbial adhesion inhibitory evaluation test was carried out in the same manner as in Examples 1-7, 1-6, and Comparative Examples 1-2, 1-1, and 1-3, except that the bacteria used in the medium in which the bacteria were suspended was Staphylococcus aureus. The results are shown in Table 5.
• Example 3-1 Comparative Examples 3-1 and 3-2
• the microbial adhesion inhibitory evaluation test was carried out in the same manner as in Example 1-6, Comparative Example 1-1, and Comparative Example 1-3, except that the bacteria used in the medium in which the bacteria were suspended was Pseudomonas aeruginosa. The results are shown in Table 6.
• the microbial adhesion-inhibiting resin of the present invention even when a nonionic copolymer is used, has the same or better microbial adhesion-inhibiting properties as conventional polymers having ionic groups such as phosphorylcholine groups.
• the biofouling-inhibiting resin of the present invention is nonionic, it can be expected to have stable microbial adhesion-inhibiting properties without being affected by pH or salt concentration. It is believed that the mechanism by which the microbial adhesion-inhibiting resin of the present invention inhibits microbial adhesion may be different from that of conventional polymers having ionic groups. For example, it is believed that the water molecules surrounding the nonionic polymer have a stable hydrated structure and have no electric charge, so that microorganisms cannot recognize the material surface, and as a result, adhesion is inhibited.

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