WO2022229633A1 - Films polymères biocompatibles à propriétés antimicrobiennes, antibactériennes et/ou antivirales - Google Patents

Films polymères biocompatibles à propriétés antimicrobiennes, antibactériennes et/ou antivirales Download PDF

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Publication number
WO2022229633A1
WO2022229633A1 PCT/GB2022/051067 GB2022051067W WO2022229633A1 WO 2022229633 A1 WO2022229633 A1 WO 2022229633A1 GB 2022051067 W GB2022051067 W GB 2022051067W WO 2022229633 A1 WO2022229633 A1 WO 2022229633A1
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Prior art keywords
biocompatible polymer
metal
coating composition
biocompatible
oxide particles
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PCT/GB2022/051067
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English (en)
Inventor
Kenneth Brian EATWELL
Muhammad Munir
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Viracoat Ltd
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Priority to EP22722870.7A priority Critical patent/EP4329493A1/fr
Publication of WO2022229633A1 publication Critical patent/WO2022229633A1/fr

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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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • A01N59/20—Copper
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/606—Coatings

Definitions

  • Biocompatible Polymer Films with Antimicrobial, Antibacterial, and/or Antiviral are Biocompatible Polymer Films with Antimicrobial, Antibacterial, and/or Antiviral
  • the present invention relates to antimicrobial, antibacterial, and/or antiviral biocompatible polymer coating compositions, biocompatible polymer films, and articles comprising biocompatible polymer films, their preparation, methods of manufacture, and their use.
  • Antimicrobial, antibacterial, and/or antiviral coatings may be used to reduce the transmission of, or kill, microbes, bacteria, and/or viruses. Such coatings may be applied to a variety of surfaces or materials for a variety of purposes.
  • the COVID-19 pandemic has caused an increased reliance on both Personal Protective Equipment (‘PPE’) and antimicrobial, antibacterial, and/or antiviral products, some of which rely on chemicals which are either potentially harmful to people or animals, or to the environment.
  • PPE Personal Protective Equipment
  • antimicrobial, antibacterial, and/or antiviral products some of which rely on chemicals which are either potentially harmful to people or animals, or to the environment.
  • a biocompatible polymer coating composition comprising: i) a polymer; ii) a crosslinking agent; iii) elemental metal, metal alloy, metal carbonate, and/or metal oxide particles; wherein components i) to iii) are dispersed in a mixture of a volatile organic solvent and water, and wherein component iii) exhibits antimicrobial, antibacterial, and/or antiviral properties.
  • a second aspect of the invention is a biocompatible polymer film obtainable by coating at least one surface of a substrate with the biocompatible polymer coating composition according to the first aspect of the invention and subsequently curing said biocompatible polymer coating composition in situ, wherein elemental metal, metal alloy, metal carbonate, and/or metal oxide particles are embedded within the biocompatible polymer film and protrude from surfaces thereof.
  • a third aspect of the invention is an article comprising a substrate and a biocompatible polymer film bound to at least one surface of said substrate, wherein elemental metal, metal alloy, metal carbonate, and/or metal oxide particles exhibiting antimicrobial, antibacterial, and/or antiviral properties are embedded within the biocompatible polymer film and protrude from surfaces thereof.
  • a fourth aspect of the invention is an item of protective equipment, the protective equipment being formed of at least one layer of a substrate material, wherein at least one layer of the substrate material is coated with a biocompatible polymer film obtainable by coating at least one surface of a substrate with the biocompatible polymer coating composition and subsequently curing said biocompatible polymer coating composition in situ, wherein elemental metal, metal alloy, metal carbonate and/or metal oxide particles are embedded within the biocompatible polymer film and protrude from surfaces thereof.
  • a fifth aspect of the invention is a method of manufacturing a biocompatible material including the steps of spraying the biocompatible polymer coating composition onto a substrate material, and curing the biocompatible polymer coating composition.
  • a sixth aspect of the invention is a method of manufacturing a biocompatible material including the steps of extruding a plastic polymer, spraying the biocompatible polymer coating composition into the extruded plastic polymer, and collecting the plastic polymer and the biocompatible polymer coating as a melt-blown material.
  • a seventh aspect of the invention is an item of personal protective equipment mask formed of the biocompatible material derived from the method of the sixth aspect of the invention, the item selected from at least one of masks, gloves, and/or tunics.
  • an item of coated fabric formed of the biocompatible material derived from the method of the sixth aspect of the invention, the item being selected from at least one of clothing, furnishings, and/or upholstery.
  • a ninth aspect of the invention is a polymer surface formed of the biocompatible material derived from the method of the sixth aspect of the invention, the item being selected from one of ventilation components and/or ventilation grills, air conditioning components and/or air conditioning grills, and/or general work surfaces.
  • an agent or material exhibits antimicrobial, antibacterial, and/or antiviral properties, this means that the agent is capable of killing or stopping the growth of microbes, bacteria, and/or viruses, respectively.
  • an agent or material is biocompatible this means that it is not harmful to living tissue (i.e. in the setting in which it is utilised the agent or material it is not toxic, harmful to physiological processes, and does not induce an immunological response).
  • a mask for a mask to be biocompatible it must not cause irritation or damage to the skin it comes into contact with on the face.
  • wt% refers to the percentage by weight a given component contributes to the total weight of a mixture (i.e. the totality).
  • Figure 1 shows a first microscope image of CU O particles protruding from the surface of a polyurethane film, in accordance with the invention disclosed herein;
  • Figure 2 shows a second microscope image of CU O particles protruding from the surface of a polyurethane film, in accordance with the invention disclosed herein;
  • Figure 3 shows a third microscope image of CU O particles protruding from the surface of a polyurethane film, in accordance with the invention disclosed herein.
  • Figure 4 show a fourth microscope image of a mixture of CU2O and Cu2(OH)2CC>3 particles protruding from the surface of a polyurethane film, in accordance with the invention disclosed herein.
  • a biocompatible polymer coating composition comprising: i) a polymer; ii) a crosslinking agent; iii) elemental metal, metal alloy, metal carbonate, and/or metal oxide particles; wherein components i) to iii) are dispersed in a mixture of a volatile organic solvent and water, and wherein component iii) exhibits antimicrobial, antibacterial, and/or antiviral properties.
  • the volatile organic solvent is miscible with water.
  • the volatile organic solvent is selected from the list consisting of acetone, dimethyl carbonate, methyl acetate, parachlorobenzotrifluoride (Oxsol 100), tert-Butyl acetate, and propylene carbonate, further preferably the volatile organic solvent is acetone.
  • the ratio of volatile organic solvent to water is 55:45 to 70:30, further preferably 60:40 to 66:33, more preferably 60:40.
  • the water is distilled de ionised water.
  • the ratio of volatile organic solvent to water is 55:45, 56:44, 57:43, 58:42, 59:41, 60:40, 61 :39, 62:38, 63:37, 64:36, 65:35, 66:34, 67:33, 68:32, 69:31 , or 70:30, or any subrange therebetween.
  • the water accounts for 7.5 wt% to 15 wt% of the biocompatible polymer coating composition, more preferably 7.5 wt% to 11.5 wt%, further preferably 8 wt% to 10 wt%, even further preferably 8 wt% to 9 wt%.
  • the water accounts for
  • the volatile organic solvent accounts for 12.5 wt% to 20 wt% of the biocompatible polymer coating composition, more preferably 13.5 wt% to 18 wt%, further preferably 15 wt% to 17.5 wt%, even further preferably 16 wt% to 17.5 wt%.
  • the volatile organic solvent accounts for 12.5, 12.6, 12.7, 12.8, 12.9, 13,
  • polymer and crosslinking agent are not particularly limited, provided they are biocompatible and compatible with each other, as would be understood by the skilled person.
  • the polymer is a polyurethane selected from the list consisting of polycarbonate-based polyurethanes, polyester-based polyurethanes, polyether-based polyurethanes, fatty acid modified polyurethanes, and UV-curable polyurethanes, further preferably a polyether-based polyurethane.
  • the polymer is in the form of a water-based polyurethane polymer dispersion (i.e. a “PUD”).
  • PUD water-based polyurethane polymer dispersion
  • polycarbonate-based PUDs, polyester-based PUDs, polyether- based PUDs, fatty acid modified PUDs, and UV-curable PUDs further preferably a polyether-based PUD.
  • the polymer is an alternating copolymer comprising di- and/or tri-isocyanate monomers and polyol monomers.
  • the di- and/or tri-isocyanate monomers may be selected from the list consisting of aliphatic diisocyanates, aromatic diisocyanates, oligomeric diisocyanates, polymeric diisocyanates, aliphatic triisocyanates, aromatic triisocyanates, oligomeric triisocyanates, and polymeric triisocyanates, for example isophorone diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, and triphenylmethane triisocyanate.
  • the polyol monomers may be selected from the list consisting of diol-containing esters, diol- containing acrylates, diol-containing carbonates, diol-containing ureas, diol-containing butadienes, diol-containing ethers, diol-containing amides, oligomeric diols, and polymeric diols.
  • Polyurethane polymer dispersions are available commercially for use in the present invention and are not particularly limited.
  • HYBRIDUR® 870 and 878 NMP-free, anionically stabilized urethane-acrylic hybrid polymer dispersion, from Air Products and Chemicals, Inc
  • HYBRIDUR® 570 and 580 urethane-acrylic hybrid polymer dispersion, from Air Products and Chemicals, Inc
  • NEOREZ® water-based polyurethanes from DSM
  • NEOPAC® water-based hybrid urethane/ acrylic hybrids from DSM
  • PICASSIAN® PU-635 aqueous aliphatic polyester urethane hybrid polymer dispersion, from Stahl
  • PICASSIAN® PU-648 aqueous, solvent free aliphatic polyether urethane hybrid polymer dispersion, from Stahl
  • Incorez CS8101 RELCA® PU-406 (aqueous, NMP free aliphatic polycarbonate urethane hybrid polymer dispersion, from Stahl), RELCA® PU-968 (aqueous, NMP free aliphatic
  • the polymer’s weight average molecular weight (M w ) is not particularly limited as the skilled person would be able to select an appropriate M w for the setting in which the biocompatible polymer composition is used; preferably, the M w is less than 200,000, more preferably less than 150,000, further preferably less than 100,000, even further preferably less than 80,000. M w is preferably more than 5,000, further preferably more than 10,000.
  • the polymer accounts for 15 wt% to 30 wt% of the biocompatible polymer coating composition, more preferably 15 wt% to 25 wt%, further preferably 17.5 wt% to 22.5 wt%, even further preferably 20 wt% to 22.5 wt%.
  • the polymer accounts for 15, 15.1, 15.2, 15.3, 15.4, 15.5, 15.6, 15.7, 15.8, 15.9, 16, 16.1, 16.2,
  • the crosslinking agent may be a polyfunctional compound wherein the polyfunctionality comprises at least one of the following functional groups: carbodiimide, glycidyl epoxide, acetoacetoxy, diacetone, alkoxysilane, amine, hydroxyl, isocyanate, aziridine, hydrazide, and epoxide.
  • the crosslinking agent is a waterbased polycarbodiimide crosslinker.
  • Crosslinkers are available commercially for use in the present invention and are not particularly limited.
  • carbodiimide crosslinkers include PICASSIAN® XL- 701 , XL-702, XL-725, XL-732, XL-755 from Stahl, ZOLDINE® XL-29SE from Angus Chemical Company, XL-1V and CX-300® from DSM Coatings, CARBODILITE® V-02, V-04, E-02, and SV-02 from GSI Exim America, and UCARLINK®XL-29SE from Union Carbide Corporation;
  • aziridine crosslinkers include CX-1 00® from DSM Coatings, and CORIAL® Hardener from BASF; isocyanate crosslinkers include BASON AT® HW 1000, BASONAT 2000, and BASONAT 3000 from BASF, ASTACIN® Hardener C I from BASF, ISONATE® and PAPI® from The Dow Chemical Company, PICASSIAN® XL-7
  • the crosslinking agent accounts for 1 wt% to 10 wt% of the biocompatible polymer coating composition, further preferably 1 wt% to 5 wt%, most preferably 1 to 3 wt%.
  • the crosslinking agent accounts for 1 , 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6,
  • the biocompatible polymer coating composition additionally comprises a coalescing agent.
  • the coalescing agent may be selected from an organic solvent and/or a plasticizer.
  • the coalescing agent comprises at least one member selected from the group consisting of butyl diglycol, ethylene glycol, propylene glycol, ethylene glycol ether, pyrrolidone, phosphate ester solvent, dibenzoate solvent, monobenzoate solvent, and phthalate solvent.
  • the coalescing agent accounts for 1 wt% to 10 wt% of the biocompatible polymer coating composition, further preferably 2 wt% to 8 wt%, most preferably 3 wt% to 5 wt%.
  • the coalescing agent accounts for 1 , 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6,
  • the biocompatible polymer coating composition additionally comprises a rheology agent.
  • the coalescing agents are available commercially for use in the present invention and are not particularly limited; for example, BYK-E410, BYK-E411, BYK-E420, BYK-7410ET, BYK-7411 ES and BYK-7420ES from BYK.
  • the rheology agent accounts for 0 wt% to 2 wt% of the biocompatible polymer coating composition, further preferably 0 wt% to 1 wt%, most preferably 0 wt% to 0.5 wt%.
  • the rheology agent accounts for 0, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1 , 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, or 2 wt% of the biocompatible polymer coating composition, or any subrange therebetween.
  • the biocompatible polymer coating composition additionally comprises a flow wetting agent.
  • the flow wetting agents are available commercially for use in the present invention and are not particularly limited; for example, SCHWEGO® flow 6527, 6533, 8057, and 8058 from Bernd Schwegmann GmbH &Co. KG, and SCHWEGO® wett 6295, 6267, and 8081 from Bernd Schwegmann GmbH &Co. KG.
  • the flow wetting agent accounts for 0 wt% to 2 wt% of the biocompatible polymer coating composition, further preferably 0 wt% to 1 wt%, most preferably 0 wt% to 0.5 wt%.
  • the rheology agent accounts for 0, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1 , 1.1 , 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, or 2 wt% of the biocompatible polymer coating composition, or any subrange therebetween.
  • the selection of elemental metal and/or metal oxide particles is not particularly limited, provided they exhibit antimicrobial, antibacterial, and/or antiviral properties.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles are selected from the group consisting of silver-containing, aluminium- containing, gold-containing, copper-containing, iron-containing, magnesium- containing, titanium-containing, or zinc-containing metal, metal alloy, metal carbonate, and/or metal oxide particles, or any combination thereof, preferably selected from Ag, AI 2 O 3 , Au, Cu, CU 2 (0H) 2 C0 3 , CUO, CU 2 0, Fe 3 C> 4 , MgO, Ti0 2 , and ZnO particles, or any combination thereof.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles are copper-containing metal, metal alloy, and/or metal oxide particles, more preferably selected from the group consisting of Cu, CU 2 (OH) 2 CC>3, CUO, CU 2 0, or any combination thereof, further preferably selected from the group consisting of Cu, CuO, and Cu 2 0 particles, or any combination thereof even further preferably CuO or Cu 2 0 particles.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles have a mean diameter of between 10 pm and 80 pm, preferably between 20 pm and 60 pm, further preferably between 30 pm and 40 pm.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles account for 40 wt% to 60 wt% of the biocompatible polymer coating composition, further preferably 45 wt% to 60 wt%, most preferably 45 wt% to 55 wt%.
  • the metal, metal alloy, metal carbonate, and/or metal oxide particles account for 40, 40.1, 40.2, 40.3, 40.4, 40.5, 40.6, 40.7, 40.8, 40.9, 41, 41.1 , 41.2, 41.3,
  • the biocompatible polymer coating composition comprises: i) 17.5 wt% to 22.5 wt% of a water-based polyurethane polymer dispersion (PUD), as defined above; ii) 1 wt% to 3 wt% of a crosslinking agent, as defined above; iii) 0 wt% to 1 wt% of a flow wetting agent, as defined above; iv) 0 wt% to 1 wt% of a rheology agent, as defined above; v) 45 wt% to 60 wt% of copper-based particles, as defined above; wherein i) to v) are dispersed in a mixture of acetone and water, wherein said acetone accounts for 15 wt% to 17.5 wt% of the biocompatible polymer coating composition and said water accounts for 8 wt% to 10 wt% of the biocompatible polymer coating composition.
  • PID water-based polyurethane polymer dispersion
  • a method of manufacturing a biocompatible polymer coating composition comprising dispersing the following components i) to iii), and optionally components iv) to vi), in a mixture of a volatile organic solvent and water: i) a polymer, preferably a water-based polyurethane dispersion (PUD); ii) a crosslinking agent; iii) elemental metal, metal alloy, metal carbonate, and/or metal oxide particles, preferably copper-containing elemental metal, metal alloy, metal carbonate, and/or metal oxide particles; iv) optionally a coalescing agent; v) optionally a rheology agent; and vi) optionally a flow wetting agent; wherein component iii) exhibits antimicrobial, antibacterial, and/or antiviral properties and components i) to vi), the volatile organic solvent, and water are defined in the preceding pages.
  • a polymer preferably a water-based polyurethane dispersion (PUD); ii) a crosslink
  • a biocompatible polymer film obtainable by coating at least one surface of a substrate with the biocompatible polymer coating composition according to the first aspect of the invention and subsequently curing said biocompatible polymer coating composition in situ, wherein elemental metal, metal alloy, metal carbonate and/or metal oxide particles are embedded within the biocompatible polymer film and protrude from surfaces thereof.
  • coating methods may utilise, for example, immersion, brush, spray, dip, curtain, agitated bath, aerated baths, or aerosol techniques to coat the biocompatible polymer composition onto the at least one surface of the substrate.
  • the biocompatible polymer composition is cured in situ onto said at least one surface of the substrate.
  • curing may be initiated by any method as would be known to the skilled person such as the application of heat, radiation, electron beams, or chemical additives.
  • accelerated drying or photocuring is utilised to cure the biocompatible polymer composition onto the at least one surface of the substrate.
  • the biocompatible polymer film has a mean thickness of between 10 pm and 100 pm, further preferably between 20 pm and 80 pm, even further preferably between 30 pm and 60 pm, most preferably between 40 pm and 50 pm.
  • the beneficial antimicrobial, antibacterial, and/or antiviral properties of the biocompatible polymer film of the present invention is realised by the protrusion of metal, metal alloy, metal carbonate, and/or metal oxide particles exhibiting antimicrobial, antibacterial, and/or antiviral properties from the surface of the polymer film.
  • the diameter of one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer, further preferably wherein between 25% and 40% of the diameter of one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer, even further preferably wherein between 30% and 35% of the diameter of one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer.
  • one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer by between 3 pm and 27 pm, preferably between 7 pm and 20 pm, further preferably between 10 pm and 13 pm.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrudes from the surface of the biocompatible polymer, further preferably wherein between 25% and 40% by mass of the total elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrudes from the surface of the biocompatible polymer, even further preferably wherein between 30% and 35% by mass of the total elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrudes from the surface of the biocompatible polymer.
  • the substrates to which the biocompatible polymer film may be applied is not particularly limited, provided that, once cured in situ, the biocompatible polymer film adheres to the substrate, as would be understood by the skilled person.
  • the substrate is selected from naturally occurring or man-made materials.
  • the substrate may be selected from plastic polymers, cloth, fabric, polyester, polypropylene, wool, plastic, cotton, spandex, paper, linoleum, silicone, latex, rubber, marble, and wood, fibrous materials derived therefrom, and mixtures or combinations thereof.
  • a third aspect of the invention is an article comprising a substrate and a biocompatible polymer film bound to at least one surface of said substrate, wherein elemental metal, metal alloy, metal carbonate, and/or metal oxide particles exhibiting antimicrobial, antibacterial, and/or antiviral properties are embedded within the biocompatible polymer film and protrude from surfaces thereof.
  • the selection of polymer of the biocompatible polymer film is not particularly limited, provided it is biocompatible, as would be understood by the skilled person.
  • the polymer of the biocompatible polymer is outlined in the first aspect of the invention.
  • the polymer of the biocompatible polymer film is selected from the list consisting of polycarbonate-based polyurethanes, polyester-based polyurethanes, polyether-based polyurethanes, fatty acid modified polyurethanes, and UV-curable polyurethanes, further preferably a polyether-based polyurethane.
  • the biocompatible polymer film has a mean thickness of between 10 pm and 100 pm, further preferably between 20 pm and 80 pm, even further preferably between 30 pm and 60 pm, most preferably between 40 pm and 50 pm.
  • the selection of elemental metal, metal alloy, metal carbonate and/or metal oxide particles is not particularly limited, provided they exhibit antimicrobial, antibacterial, and/or antiviral properties.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles are selected from the group consisting of silver-containing, aluminium- containing, gold-containing, copper-containing, iron-containing, magnesium- containing, titanium-containing, or zinc-containing metal, metal alloy, metal carbonate, and/or metal oxide particles, or any combination thereof, preferably selected from Ag, AI2O3, Au, Cu, CU 2 (0H) 2 C0 3 , CUO, CU 2 0, Fe 3 C> 4 , MgO, Ti0 2 , and ZnO particles, or any combination thereof.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles are copper-containing metal, metal alloy, metal carbonate, and/or metal oxide particles, or any combination thereof, more preferably selected from the group consisting of Cu, Cu 2 (OH) 2 CC>3, CuO, Cu 2 0, or any combination thereof, further preferably selected from the group consisting of Cu, CuO, and Cu 2 0 particles, or any combination thereof, even further preferably CuO or Cu 2 0 particles.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles have a mean diameter of between 10 pm and 80 pm, preferably between 20 pm and 60 pm, further preferably between 30 pm and 40 pm.
  • the beneficial antimicrobial, antibacterial, and/or antiviral properties of the biocompatible polymer film of the present invention is realised by the protrusion of metal, metal alloy, metal carbonate, and/or metal oxide particles exhibiting antimicrobial, antibacterial, and/or antiviral properties from the surface of the polymer film.
  • the diameter of one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer, further preferably wherein between 25% and 40% of the diameter of one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer, even further preferably wherein between 30% and 35% of the diameter of one or more of the elemental metal, metal carbonate, metal alloy, and/or metal oxide particles protrude from the surface of the biocompatible polymer.
  • one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer by between 3 pm and 27 pm, preferably between 7 pm and 20 pm, further preferably between 10 pm and 13 pm.
  • the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrudes from the surface of the biocompatible polymer, further preferably wherein between 25% and 40% by mass of the total elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrudes from the surface of the biocompatible polymer, even further preferably wherein between 30% and 35% by mass of the total elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrudes from the surface of the biocompatible polymer.
  • the substrates to which the biocompatible polymer film may be applied is not particularly limited, provided that, once cured in situ, the biocompatible polymer film adheres to the substrate, as would be understood by the skilled person.
  • the substrate is selected from naturally occurring or man-made materials.
  • the substrate may be selected from plastic polymers, cloth, fabric, polyester, polypropylene, wool, plastic, cotton, spandex, paper, linoleum, silicone, latex, rubber, marble, and wood, fibrous materials derived therefrom, and mixtures or combinations thereof.
  • the article is obtainable by coating at least one surface of a substrate with the biocompatible polymer coating composition according to the first aspect of the invention and subsequently curing said biocompatible polymer coating composition in situ, wherein elemental metal and/or metal oxide particles are embedded within the biocompatible polymer film and protrude from surfaces thereof.
  • antimicrobial, antibacterial, and/or antiviral biocompatible polymer coating compositions described herein may be applied to a variety of different materials, substrates, and/or products, and may be used for a variety of applications.
  • PPE Personal Protective Equipment
  • antimicrobial, antibacterial, and/or antiviral biocompatible polymer coating compositions may be the application to PPE, namely facemasks.
  • This application may be achieved in a number of ways, and the coating compositions described herein may be applied do different types of facemasks in a variety of different ways.
  • ‘N95’ and/or ‘KN95’ masks are formed from multiple layers of synthetic material, often a polypropylene plastic polymer, and such masks are designed to be worn over the mouth and nose. These masks are designed to filter out and capture 95 percent of 0.3-micron particles in the air - giving rise to the designation of ’95’ in the name.
  • COVID-19 particles are of around 0.1 -micron size, but are often attached to larger particles in the air.
  • ‘N95’ and ‘KN95’ masks are generally formed from layers of a polypropylene or polyurethane plastic polymer, which is ‘melt-blown’ and then fashioned into a mask.
  • the plastic polymer generally provided in pellet form, are fed into a drum, passed through a corkscrew arrangement to convey the pellets into a heater, heated, passed through a mandrel at around 300°C and then extruded in a continuous strand. This causes spiral-like fibres to be formed of the polymer, and resembles candyfloss when it passes out of the mandrel.
  • the extruded polymer is then conveyed onto heated rollers, passed through the heated rollers and compressed into a sheet, and wound onto a roller for later use.
  • This melt-blown fabric may then be formed into masks.
  • ‘N95’ and ‘KN95’ masks are often formed of at least three layers of the melt-blown fabric.
  • the antimicrobial, antibacterial, and/or antiviral biocompatible polymer coating compositions described herein may be sprayed onto the melt-blown fabric before it is formed into masks. This may take the form of a simple spraying operation, with the polymer cured after the spraying operation. In an example, three spraying operations may be carried out to ensure appropriate coverage of the fabric with the polymer coating, whilst still allowing for appropriate air passage through the fabric.
  • the polymer coating When the polymer coating is sprayed onto the melt-blown fabric, the polymer coats individual strands of the fabric. By the nature of the melt-blown material allowing air to pass therethrough, there is space for the polymer to coat each individual fibre.
  • the melt-blown fabric is produced and fed into an arrangement for carrying out the spraying and impregnation of the polymer.
  • the polymer may be sprayed onto the fabric as part of a first pass, the material heated, and then looped back for a further spray, heating, and then a final spray and heating, before being packed on a roller ready for shipping and use.
  • the heating process causes accelerated drying of the polymer.
  • the temperature at which this may be carried out is around 40°C and may utilise hot air. It is envisaged, however, that the polymer coating may be cured with UV light, using a generic cross linker with a photoinhibitor, which may be operable as a photocatalyst.
  • the polymer coating may be sprayed into the ‘open’ fibres of the melt-blown fabric before it reaches the rollers, so that the polymer may be formed into the melt-blown fabric, without having to be applied to the fabric as a separate step.
  • the antimicrobial, antibacterial, and/or antiviral biocompatible polymer coating compositions for fabric are suitable for application to PPE such as masks, but may also be applied to so-called ‘first-touch’ surfaces and fabrics which may include seat-belts and seats of vehicles.
  • the fabric allows the polymer to penetrate.
  • the antimicrobial, antibacterial, and/or antiviral biocompatible polymer coating compositions may be used to form PPE which may be masks, gloves, tunics, scrubs, headwear, general garments, or any other suitable sort of PPE, which will be understood by the skilled reader.
  • the antimicrobial, antibacterial, and/or antiviral biocompatible polymer coating compositions may be used to form more general garments, or the first touch surfaces described above, and these garments or surfaces may include, clothing, furnishings, upholstery, ventilation components and/or ventilation grills, air conditioning components and/or air conditioning grills, and/or general work surfaces, or any other fabric or material which will be understood by the skilled reader.
  • the antimicrobial, antibacterial, and/or antiviral biocompatible polymer coating compositions may include a colouring agent or dye, so that the coating when applied to a substrate, for example a mask, is of a particular colour.
  • a colour may derive from the salt of copper in the polymer coating.
  • this may be copper carbonate, such that the resulting polymer coating is green in colour.
  • the biocompatible polymer coating composition of Example 1 is cured in situ on a substrate utilising accelerated drying.
  • Fig. 1-3 show microscope images of the resultant film.
  • a biocompatible polymer coating composition comprising: i) a polymer; ii) a crosslinking agent; iii) elemental metal, metal alloy, metal carbonate, and/or metal oxide particles; wherein components i) to iii) are dispersed in a mixture of a volatile organic solvent and water, and wherein component iii) exhibits antimicrobial, antibacterial, and/or antiviral properties.
  • a polymer ii) a crosslinking agent
  • iii) elemental metal, metal alloy, metal carbonate, and/or metal oxide particles wherein components i) to iii) are dispersed in a mixture of a volatile organic solvent and water, and wherein component iii) exhibits antimicrobial, antibacterial, and/or antiviral properties.
  • biocompatible polymer coating composition according to embodiment 1, wherein the volatile organic solvent is miscible with water.
  • biocompatible polymer coating composition according to embodiment 1 or 2, wherein the volatile organic solvent is selected from the list consisting of acetone, dimethyl carbonate, methyl acetate, parachlorobenzotrifluoride (Oxsol 100), tert-Butyl acetate, and propylene carbonate.
  • volatile organic solvent selected from the list consisting of acetone, dimethyl carbonate, methyl acetate, parachlorobenzotrifluoride (Oxsol 100), tert-Butyl acetate, and propylene carbonate.
  • biocompatible polymer coating composition according to any of embodiments 1 to 3, wherein the volatile organic solvent is acetone.
  • biocompatible polymer coating composition according to any of embodiments 1 to 4, wherein the ratio of volatile organic solvent to water is 55:45 to 70:30 Embodiment 6.
  • biocompatible polymer coating composition according to embodiment 5, wherein the ratio of volatile organic solvent to water is 60:40 to 66:33.
  • Embodiment 7 The biocompatible polymer coating composition according to embodiment 6, wherein the ratio of volatile organic solvent to water is 60:40.
  • biocompatible polymer coating composition according to any of embodiments 1 to 7, wherein the polymer is a polyurethane polymer.
  • biocompatible polymer coating composition wherein the polymer is a polyurethane polymer selected from the list consisting of polycarbonate-based polyurethanes, polyester-based polyurethanes, polyether-based polyurethanes, fatty acid modified polyurethanes, and UV- curable polyurethanes.
  • polyurethane polymer selected from the list consisting of polycarbonate-based polyurethanes, polyester-based polyurethanes, polyether-based polyurethanes, fatty acid modified polyurethanes, and UV- curable polyurethanes.
  • biocompatible polymer coating composition according to any of embodiments 1 to 9, wherein the polymer is in the form of a water-based polyurethane polymer dispersion (PUD).
  • PLD polyurethane polymer dispersion
  • biocompatible polymer coating composition wherein the PUD is selected from the list consisting of polycarbonate-based PUDs, polyester-based PUDs, polyether-based PUDs, fatty acid modified PUDs, and UV-curable PUDs.
  • biocompatible polymer coating composition according to any of embodiments 1 to 11, wherein the polymer of the polymer is an alternating copolymer.
  • biocompatible polymer coating composition according to embodiment 12, wherein the polymer comprises di- and/or tri-isocyanate monomers and polyol monomers.
  • Embodiment 14 The biocompatible polymer coating composition according to embodiment 13, wherein the di- and/or tri-isocyanate monomers are selected from aliphatic diisocyanates, aromatic diisocyanates, oligomeric diisocyanates, polymeric diisocyanates, aliphatic triisocyanates, aromatic triisocyanates, oligomeric triisocyanates, and polymeric triisocyanates.
  • the di- and/or tri-isocyanate monomers are selected from aliphatic diisocyanates, aromatic diisocyanates, oligomeric diisocyanates, polymeric diisocyanates, aliphatic triisocyanates, aromatic triisocyanates, oligomeric triisocyanates, and polymeric triisocyanates.
  • biocompatible polymer coating composition wherein the di- and/or tri-isocyanate monomers are selected from isophorone diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, and triphenylmethane triisocyanate.
  • biocompatible polymer coating composition according to any of embodiments 13 to 15, wherein the polyol monomers are selected from diol- containing esters, diol-containing acrylates, diol-containing carbonates, diol- containing ureas, diol-containing butadienes, diol-containing ethers, diol- containing amides, oligomeric diols, and polymeric diols.
  • the polyol monomers are selected from diol- containing esters, diol-containing acrylates, diol-containing carbonates, diol- containing ureas, diol-containing butadienes, diol-containing ethers, diol- containing amides, oligomeric diols, and polymeric diols.
  • biocompatible polymer coating composition according to any of embodiments 1 to 16, wherein the polymer has a weight average molecular weight (M w ) of less than 200,000 and more than 5,000.
  • biocompatible polymer coating composition according to any of embodiments 1 to 17, wherein the crosslinking agent is a polyfunctional compound comprising at least one functional group selected from the group consisting of carbodiimide, glycidyl epoxide, acetoacetoxy, diacetone, alkoxysilane, amine, hydroxyl, isocyanate, aziridine, hydrazide, and epoxide.
  • the crosslinking agent is a polyfunctional compound comprising at least one functional group selected from the group consisting of carbodiimide, glycidyl epoxide, acetoacetoxy, diacetone, alkoxysilane, amine, hydroxyl, isocyanate, aziridine, hydrazide, and epoxide.
  • biocompatible polymer coating composition to any of embodiments 1 to 18, wherein the biocompatible polymer coating composition additionally comprises a coalescing agent, preferably wherein the coalescing agent is selected from an organic solvent and/or a plasticizer.
  • Embodiment 20 is a diagrammatic representation of Embodiment 20.
  • biocompatible polymer coating composition to any of embodiments 1 to 4.
  • the biocompatible polymer coating composition additionally comprises a rheology agent, preferably wherein the rheology agent is selected from BYK-E410, BYK-E411, BYK-E420, BYK-7410ET, BYK-7411ES and BYK- 7420ES.
  • biocompatible polymer coating composition to any of embodiments 1 to 4.
  • the biocompatible polymer coating composition additionally comprises a flow wetting agent, preferably wherein the rheology agent is selected from SCHWEGO® flow 6527, SCHWEGO® flow 6533, SCHWEGO® flow 8057, SCHWEGO® flow 8058, SCHWEGO® wett 6295, SCHWEGO® wett 6267, and SCHWEGO® wett.
  • a flow wetting agent preferably wherein the rheology agent is selected from SCHWEGO® flow 6527, SCHWEGO® flow 6533, SCHWEGO® flow 8057, SCHWEGO® flow 8058, SCHWEGO® wett 6295, SCHWEGO® wett 6267, and SCHWEGO® wett.
  • a biocompatible polymer film obtainable by coating at least one surface of a substrate with the biocompatible polymer coating composition according to any of embodiments 1 to 21 and subsequently curing said biocompatible polymer coating composition in situ, wherein elemental metal, metal alloy, metal carbonate, and/or metal oxide particles are embedded within the biocompatible polymer film and protrude from surfaces thereof.
  • biocompatible polymer film according to embodiment 21 or 22, wherein the curing is initiated by the application of heat, radiation, electron beams, or chemical additives, preferably accelerated drying or photocuring is utilised to cure the biocompatible polymer composition onto the at least one surface of the substrate.
  • An article comprising a substrate and a biocompatible polymer film bound to at least one surface of said substrate, wherein elemental metal, metal carbonate, metal alloy, and/or metal oxide particles exhibiting antimicrobial, antibacterial, and/or antiviral properties are embedded within the biocompatible polymer film and protrude from surfaces thereof.
  • polymer of the biocompatible polymer film is selected from the list consisting of polycarbonate- based polyurethanes, polyester-based polyurethanes, polyether-based polyurethanes, fatty acid modified polyurethanes, and UV-curable polyurethanes.
  • Embodiment 28. The biocompatible polymer coating composition, biocompatible polymer film, or article according to embodiment 27, wherein the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles are selected from the group consisting of Cu, Cu2(OH)2CC>3, CuO, and CU2O particles, or any combination thereof.
  • biocompatible polymer coating composition biocompatible polymer film, or article according to embodiment 28, wherein the elemental metal, metal alloy, and/or metal oxide particles are selected from the group consisting of Cu, CuO, and CU2O, or any combination thereof.
  • Embodiment 30 is a diagrammatic representation of Embodiment 30.
  • biocompatible polymer coating composition biocompatible polymer film, or article according to embodiment 29, wherein the elemental metal, metal alloy, and/or metal oxide particles are CuO or CU2O particles.
  • biocompatible polymer coating composition biocompatible polymer film, or article according to any of embodiments 1 to 30, wherein the elemental metal, metal alloy, and/or metal oxide particles have a mean diameter of between 10 pm and 80 pm.
  • biocompatible polymer coating composition biocompatible polymer film, or article according to embodiment 31, wherein the elemental metal, metal alloy, and/or metal oxide particles have a mean diameter of between 20 pm and 60 pm.
  • biocompatible polymer coating composition biocompatible polymer film, or article according to embodiment 32, wherein the elemental metal, metal alloy, and/or metal oxide particles have a mean diameter of between 30 pm and 40 pm.
  • Embodiment 34 Embodiment 34.
  • biocompatible polymer film or article according to any of embodiments 22 to 33, wherein the biocompatible polymer film has a mean thickness of between 10 pm and 100 pm.
  • Embodiment 35 The biocompatible polymer film or article according to any of embodiments 22 to 33, wherein the biocompatible polymer film has a mean thickness of between 10 pm and 100 pm.
  • biocompatible polymer film or article according to embodiment 34 wherein the biocompatible polymer film has a mean thickness of between 20 pm and 80 pm.
  • Embodiment 36 The biocompatible polymer film or article according to embodiment 35, wherein the biocompatible polymer film has a mean thickness of between 30 pm and 60 pm.
  • biocompatible polymer film or article according to embodiment 36 wherein the biocompatible polymer film has a mean thickness of between 40 pm and
  • biocompatible polymer film or article according to embodiment 38 wherein between 25% and 40% of the diameter of one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer.
  • Embodiment 40 is a diagrammatic representation of Embodiment 40.
  • biocompatible polymer film or article according to embodiment 39 wherein between 30% and 35% of the diameter of one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer.
  • biocompatible polymer film or article according to embodiment 41 wherein one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer by between 7 pm and 20 pm.
  • biocompatible polymer film or article according to embodiment 42 wherein one or more of the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles protrude from the surface of the biocompatible polymer by between 10 pm and 13 pm.
  • biocompatible polymer film or article wherein the substrate is selected from from plastic polymers, cloth, fabric, polyester, polypropylene, wool, plastic, cotton, spandex, paper, linoleum, silicone, latex, rubber, marble, and wood, fibrous materials derived therefrom, and mixtures or combinations thereof.
  • a biocompatible polymer coating composition comprising: i) 15 wt% to 30 wt% of a polymer; ii) 1 wt% to 10 wt% of a crosslinking agent; iii) 40 wt% to 60 wt% of elemental metal, metal alloy, metal carbonate, and/or metal oxide particles; wherein i) to iii) are dispersed in a mixture of acetone and water, wherein said acetone accounts for 12.5 wt% to 20 wt% of the biocompatible polymer coating composition and said water accounts for 7.5 wt% to 15 wt% of the biocompatible polymer coating composition.
  • Embodiment 46 Embodiment 46.
  • biocompatible polymer coating composition according to embodiment 45, wherein the polymer is a water-based polyurethane polymer dispersion (PUD) and the elemental metal, metal alloy, metal carbonate, and/or metal oxide particles are copper-based particles.
  • PLD polyurethane polymer dispersion
  • the biocompatible polymer coating composition according to embodiment 46 comprising: i) 17.5 wt% to 22.5 wt% of a water-based polyurethane polymer dispersion (PUD), as defined above; ii) 1 wt% to 3 wt% of a crosslinking agent, as defined above; iii) 0 wt% to 1 wt% of a flow wetting agent, as defined above; iv) 0 wt% to 1 wt% of a rheology agent, as defined above; v) 45 wt% to 60 wt% of copper-based particles, as defined above; wherein i) to v) are dispersed in a mixture of acetone and water, wherein said acetone accounts for 15 wt% to 17.5 wt% of the biocompatible polymer coating composition and said water accounts for 8 wt% to 10 wt% of the biocompatible polymer coating composition.
  • PID water-based polyurethane polymer disper

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Abstract

Une composition de revêtement polymère biocompatible comprend un polymère, un agent de réticulation, un métal élémentaire, un alliage métallique, un carbonate métallique et/ou des particules d'oxyde métallique. Les composants sont dispersés dans un mélange d'un solvant organique volatil et d'eau, de telle sorte que le métal élémentaire, l'alliage métallique, le carbonate métallique et/ou les particules d'oxyde métallique présentent des propriétés antimicrobiennes, antibactériennes et/ou antivirales. Ce revêtement polymère biocompatible peut être utilisé pour former au moins une couche d'un article d'équipement de protection, de telle sorte qu'au moins une couche d'un matériau de substrat est revêtue d'un film polymère biocompatible.
PCT/GB2022/051067 2021-04-27 2022-04-27 Films polymères biocompatibles à propriétés antimicrobiennes, antibactériennes et/ou antivirales WO2022229633A1 (fr)

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