CN102272245A - 抗微生物的uv可固化涂料组合物 - Google Patents

抗微生物的uv可固化涂料组合物 Download PDF

Info

Publication number
CN102272245A
CN102272245A CN2009801542921A CN200980154292A CN102272245A CN 102272245 A CN102272245 A CN 102272245A CN 2009801542921 A CN2009801542921 A CN 2009801542921A CN 200980154292 A CN200980154292 A CN 200980154292A CN 102272245 A CN102272245 A CN 102272245A
Authority
CN
China
Prior art keywords
antimicrobial
reagent
acrylic acid
weight parts
curable compositions
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN2009801542921A
Other languages
English (en)
Inventor
D·T-T·奥-扬
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Becton Dickinson and Co
Original Assignee
Becton Dickinson and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Becton Dickinson and Co filed Critical Becton Dickinson and Co
Publication of CN102272245A publication Critical patent/CN102272245A/zh
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—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
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A61L29/16—Biologically active materials, e.g. therapeutic substances
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0254—After-treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
    • B05D3/065—After-treatment
    • B05D3/067—Curing or cross-linking the coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
    • B05D7/04—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber to surfaces of films or sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/104—Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
    • C09D5/1662—Synthetic film-forming substance
    • C09D5/1668—Vinyl-type polymers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/20—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/40—Esters containing free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
    • C10M105/58—Amines, e.g. polyalkylene polyamines, quaternary amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/04—Metals; Alloys
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/06—Sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/16—Hydrogen peroxide; Oxygenated water
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/20—Compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/26—Compounds containing silicon or boron, e.g. silica, sand
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/24—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/204—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
    • A61L2300/206—Biguanides, e.g. chlorohexidine
    • 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
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/204—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
    • A61L2300/208—Quaternary ammonium compounds
    • 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
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/105—Silica
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
    • C10M2229/0515—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/055—Particles related characteristics
    • C10N2020/06—Particles of special shape or size
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/16—Antiseptic; (micro) biocidal or bactericidal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Plant Pathology (AREA)
  • Plasma & Fusion (AREA)
  • Physics & Mathematics (AREA)
  • Emergency Medicine (AREA)
  • Metallurgy (AREA)
  • Materials For Medical Uses (AREA)
  • Paints Or Removers (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Lubricants (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

本发明公开了抗微生物组合物和方法。所述抗微生物组合物在向广泛的医疗器械提供抗微生物能力方面特别有用。在一个方面中，本发明涉及一种包含UV可固化组合物的UV可固化抗微生物涂料，所述UV可固化组合物包含能够一起形成UV可固化聚合物组合物的低聚物、单体和光引发剂。如果需要，所述组合物可包括流变改性剂。所述组合物还包括抗微生物试剂，所述抗微生物试剂可选自多种试剂。代表性的抗微生物试剂包括氯化十六烷基非那吡啶、西曲溴铵、阿来西定、氯己定二乙酸盐、苯扎氯铵和邻苯二甲醛。

Description

抗微生物的UV可固化涂料组合物
发明背景
本发明涉及抗微生物组合物和在各种医疗应用中使用这些组合物的方法。现代医学治疗的一个主要挑战是控制感染和微生物有机体的传播。
始终存在这种挑战的一个领域是各种类型的输液治疗。输液治疗是一种最普通的健康护理程序。就医、家庭护理和其他患者通过插入血管系统中的血管接入器械来接收流体、医药品和血液产品。可使用输液治疗来治疗感染、提供麻醉或使得痛觉缺失、提供营养支持、治疗肿瘤的生长、保持血压和心律、或用于许多其他临床上重要的用途。
通过血管接入器械可有助于输液治疗。所述血管接入器械可接入患者的外周或中心血管系统。所述血管接入器械可短期(数天)、中期(数周)或长期(数月到数年)留置。可将所述血管接入器械用于连续输液治疗或间歇治疗。
普通的血管接入器械是一种置入患者静脉内的塑料导管。所述导管的长度可从用于外周接入的几个厘米到用于中心接入的数厘米且可包括诸如经外周中心静脉置管(PICC)的器械。所述导管可经皮植入或通过外科手术植入患者皮肤之下。所述导管或连接到所述导管的任意一种其他血管接入器械可具有单一内腔或多个内腔以用于同时输入多种流体。
血管接入器械通常包括可连接到其他医疗器械的Luer适配器。例如，可将给药设备可一端连接到血管接入器械，而另一端连接脉注射物(IV)袋。所述给药设备是用于连续灌输流体和医药品的流体导管。通常，IV接入器械是可连接到另一个血管接入器械的血管接入器械，其可关闭所述血管接入器械并使得可间歇灌输或注射流体和医药品。IV辅助器械可包括外壳和用于关闭所述系统的隔片。所述隔片可用医疗装置的钝套管或阳式Luer打开。
当血管接入器械的隔片不能正常打开或设计特征具有缺陷时，可造成特定的并发症。与输液治疗相关的并发症可造成明显的病态，甚至死亡。一种显著的并发症是导管相关性血流感染(CRBSI)。在美国的医院中每年发生大约250000～400000个与BSI相关的中心静脉导管(CVC)病例。每次感染将死亡率提高约12％～25％且每个病例的健康护理系统的成本为25000～56000美金。
血管接入器械可充当感染的滋生地，导致散布BSI(血流感染)。因难以有规律地对所述器械进行冲洗、未消毒的置入技术、或因通过所述通道的任一端进入流体流动通道并随后进入导管置入物中的病原体可造成这种情况。当血管接入器械发生污染时，病原体粘附到所述血管接入器械，发生繁殖并形成生物膜。所述生物膜可抵抗大部分生物杀灭剂并为病原体提供了补充来源而进入到患者血流中，造成BSI。由此，需要具有抗微生物性能的器械。
阻止生物膜的形成和患者感染的一种方法是在医疗器械和元件上提供抗微生物涂层。许多医疗器械是由金属材料或聚合物材料制成的。这些材料通常具有高的摩擦系数。通常将具有低摩擦系数的低分子量材料混入材料主体或涂覆在基底表面上以有助于器械的功能性。
在过去35年间，通常实践的是将热塑性聚氨酯溶液用作抗微生物涂料的载体。溶剂通常为四氢呋喃(THF)、二甲基甲酰胺(DMF)或所述两者的共混物。因为THF能够非常快速被氧化且非常易于爆炸，所以需要昂贵的防爆涂覆设施。这些苛刻的溶剂也会攻击通常使用的许多聚合物材料，所述聚合物材料包括聚氨酯、有机硅、聚异戊二烯、丁基橡胶、聚碳酸酯、硬质聚氨酯、硬质聚氯乙烯、丙烯酸系材料和丁苯橡胶(SBR)。因此，由这些材料制成的医疗器械能够随时间而变形和/或在其表面上形成微裂缝。这种涂料的另一个问题是将溶剂完全热蒸发掉需要花费几乎24小时。因此，常规技术永远存在加工、性能和成本的问题。
另一个限制是合适的抗微生物试剂在这种涂料中的可用性。在涂覆医疗器械中所使用的最常用的抗微生物试剂是银。银盐和银元素在医疗外科行业和普通行业两者中都是熟知的抗微生物试剂。通常将其并入聚合物本体材料中或通过等离子体、热蒸发、电镀、或通过常规的溶剂涂覆技术将其涂覆在医疗器械表面上。这些技术冗长、昂贵且环境不友好。
另外，银涂覆的医疗器械的性能至多算作中等。例如，在由银盐或银元素的离子化而得到的银离子实现作为抗微生物试剂的功效之前，需花费高达八(8)小时。因此，在银涂层恰好发挥功效之前，大量的微生物活性也已发生。此外，银化合物或银元素具有从暗琥珀色到黑色的令人不悦的颜色。
因此，本领域中需要改进的组合物以为各种医疗器械、尤其是关于输液治疗的器械提供抗微生物能力。具体地，需要一种能够容易地施涂到由聚合物材料和金属构造的医疗器械上的有效的抗微生物涂料。还需要一种改良方法，以将这种抗微生物涂料涂覆到医疗器械上。
发明概述
针对本领域中通过目前可获得的抗微生物组合物和方法尚未完全解决的问题和需要，完成了本发明。因此，通过提供与医疗器械一起使用的抗微生物组合物和方法，开发了这些组合物和方法以减少诸如CRBSI的并发症的危险和几率。
本发明涉及具有抗微生物性能的紫外线(UV)(大约200nm～600nm的波长)可固化涂料。通过在上述范围内即约200nm～约600nm的光可将所述涂料固化。在某些实施方案中，优选利用约300nm～约450nm范围内的光将所述组合物固化。这些涂料特别适合用在医疗器械上，特别是像无针阀的血管内接入装置。如上所述，所述医疗器械通常有聚合物基材、尤其是聚碳酸酯(PC)、聚氨酯(PU)、聚氯乙烯(PVC)、丁苯橡胶(SBR)和丙烯酸系材料构成。
在本发明的一个方面中，利用UV可固化涂料(下文中有时称作“UV”涂料)对这种器械的表面进行涂覆，所述UV可固化涂料包含UV可固化的组合物和并入其中的其他成分例如均匀分布在其整个基体中的抗微生物试剂。所述抗微生物试剂能够扩散通过所述基体并杀死与所述涂层料表面接触的微观有机体。当通过IV流体将基体软化时，均匀分布在UV涂料基体中的抗微生物试剂逐渐从所述基体中扩散出去。然后，可利用抗微生物试剂将与涂料表面接触的微生物杀死。
本发明的制剂通常由聚氨酯或聚酯型低聚物与丙烯酸酯型官能团、丙烯酸酯型单体、光引发剂、流变改性剂和抗微生物试剂的组合构成。纳米级或微米级的抗微生物试剂颗粒均匀并永久地分布在整个涂料基体中。
所述涂料是无溶剂的且通过使用其他常规涂覆方法能够将其喷施、擦拭、浸渍或分布以涂覆到基底表面上。然后，利用紫外光将其快速固化。可在数秒或数分钟内使其完成固化，这取决于制剂和固化条件。本发明的涂料通常在数分钟内产生效用，而不像常规涂料在数小时后产生效用。所述涂料通常还具有令人舒适的浅颜色或者甚至是透明色。
在本发明的范围内，能够使用多种低聚物。仅需要所述低聚物能够进行UV固化且能够携带本文中所述类型的抗微生物试剂。例如，所述低聚物能够为丙烯酸改性的脂族聚氨酯、丙烯酸改性的芳族聚氨酯、丙烯酸改性的聚酯、不饱和聚酯、丙烯酸改性的聚醚、丙烯酸改性的丙烯酸系材料等、或上述物质的组合。所述丙烯酸改性的官能团能够为单官能、二官能、三官能、四官能、五官能或六官能的。
如同所述低聚物一样，在本组合物中能够使用多种单体。再次，仅需要总体组合物是UV可固化的且所述组合物能够携带抗微生物试剂。例如，所述单体能够为丙烯酸2-乙基己基酯、丙烯酸异辛酯、丙烯酸异冰片酯、1，6-己二醇二丙烯酸酯、二甘醇二丙烯酸酯、三甘醇二丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇三丙烯酸酯、二甲氧基苯基苯乙酮己基甲基丙烯酸酯、1，6-己二醇甲基丙烯酸酯等、或这些化合物的组合。
为了允许进行UV固化，所述组合物应具有足够的且相容的光引发剂。在本发明的特定实施方案中，所述光引发剂能够为：1)单分子分裂型，例如苯偶姻醚、苯乙酮、苯甲酰基肟和酰基氧化膦；和2)氢夺取型，诸如米蚩酮、噻吨酮、蒽醌(anthroguionone)、二苯甲酮、甲基二乙醇胺和2-N-丁氧基乙基-4-(二甲氨基)苯甲酸盐等、或这些物质的组合。
在特定实施方案中，优选向所述组合物中添加流变改性剂。所述流变改性剂使得可根据需要对所述组合物的流动特性进行控制和改进。所述流变改性剂还有助于抗微生物试剂和其他材料在所述组合物内的均匀分布。合适的流变改性剂可包括有机粘土、蓖麻蜡、聚酰胺蜡、聚氨酯和热解二氧化硅或这些物质的组合。
可将多种抗微生物试剂用于本发明的组合物中。仅需要所述抗微生物试剂与所述组合物的其他成分相容且其可有效地控制微生物试剂。具体地，优选的是，所述抗微生物试剂不会与组合物的其他成分发生化学反应。如上所述，在特定实施方案中，优选的是，所述抗微生物试剂能够在组合物的基体内发生移动，从而能够将其传送到微生物试剂的位置处。在本发明范围内的合适的抗微生物试剂的实例包括醛、N-酰苯胺、双胍、银元素或其化合物、双酚、和季铵化合物等、或上述物质的组合。
在另一个方面中，本发明可以是无溶剂的。如上所述，许多常规涂料使用苛刻的溶剂例如THF和DMF。可在不使用溶剂的条件下运行本发明，因此，本发明避免了因使用常规溶剂而带来的困难。
所述制剂对许多塑料表面(例如PC、PU、PVC、丙烯酸系材料和SBR)还显示了良好的粘附力。所述制剂能够被足够的紫外光(波长为大约200nm～600nm，且在特定实施方案中为约300nm～约450nm)所固化。
因此，本发明提供抗微生物涂料组合物，其克服了现有技术的许多限制。本发明使用被医疗用途所接受的已知成分。将这些成分合并并容易且高效地进行使用。如上所述，本发明的组合物通常包括低聚物、单体、光引发剂、流变改性剂和合适的抗微生物试剂。制得的组合物易于施涂到医疗器械的表面上并通过UV光快速固化。
发明详述
本发明的这种详细说明提供了本发明上述各个方面的其他说明。在本发明的一个方面中，提供一种抗微生物的紫外线(UV)可固化涂料。所述涂料包含UV可固化组合物，所述UV可固化组合物包含低聚物、单体和光引发剂，它们一起能够形成UV可固化聚合物组合物。在特定实施方案中，所述组合物可还包括流变改性剂，以改善所述组合物的流动特性和成分在所述组合物内的均匀分布。最后，可并入在UV可固化涂料组合物中的是有效的抗微生物试剂。
所述UV可固化涂料组合物主要由一种或多种低聚物和一种或多种单体、以及一种或多种合适的光引发剂组成。在下列讨论中，所述UV可固化涂料组合物将占100重量份。添加到UV可固化涂料组合物中的物质可包括流变改性剂、抗微生物试剂和其他添加剂。以添加到100重量份UV可固化涂料组合物中的重量份来定义这些物质。
所述低聚物通常选自丙烯酸改性的脂族聚氨酯、丙烯酸改性的芳族聚氨酯、丙烯酸改性的聚酯、不饱和聚酯、丙烯酸改性的聚醚、丙烯酸改性的丙烯酸系材料等、或其组合。所述丙烯酸改性的官能团选自单官能、二官能、三官能、四官能、五官能和六官能的丙烯酸酯。在本发明的范围内可使用与所述组合物的其他成分相容的任何低聚物。所述低聚物典型地占UV可固化组合物的约10％～约90％。在某些实施方案中，所述低聚物占所述UV可固化组合物的约20％～约80％。在本发明的特定实施方案中，所述低聚物占所述UV可固化组合物的约30％～约70％。
所述单体选自丙烯酸2-乙基己基酯、丙烯酸异辛酯、丙烯酸异冰片酯、1，6-己二醇二丙烯酸酯、二甘醇二丙烯酸酯、三甘醇二丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇三丙烯酸酯、二甲氧基苯基苯乙酮己基甲基丙烯酸酯、1，6-己二醇甲基丙烯酸酯等、或这些化合物的组合。再次，在本发明的范围内可使用与所述组合物的其他成分相容的任何单体。所述单体典型地占所述UV可固化组合物的约5％～约90％。在某些实施方案中，所述单体占所述UV可固化组合物的约10％～约75％。在本发明的特定实施方案中，所述单体占所述UV可固化组合物的约20％～约60％。
所述光引发剂选自：单分子分裂型例如苯偶姻醚、苯乙酮、苯甲酰基肟和酰基氧化膦；和由米蚩酮、噻吨酮、蒽醌(anthroguionone)、二苯甲酮、甲基二乙醇胺和2-N-丁氧基乙基-4-(二甲氨基)苯甲酸盐构成的氢夺取型。也可以选择所述光引发剂以使得其与在本发明的范围内可使用的其他成分相容。所述光引发剂典型地占所述UV可固化组合物的约0.5％～约10％。在某些实施方案中，所述光引发剂占所述UV可固化组合物的约1％～约8.5％。在本发明的特定实施方案中，所述光引发剂占所述UV可固化组合物的约2％～约7％。
如上所述，可向所述UV可固化组合物中添加某些其他成分。其中主要的是合适的流变改性剂和抗微生物试剂。如上所述，这些其他成分的量以添加到100重量份UV可固化组合物中的重量份表示。
所述流变改性剂选自有机粘土、蓖麻蜡、聚酰胺蜡、聚氨酯和热解二氧化硅。所述流变改性剂通常构成添加到100重量份UV可固化组合物中的约0.1～约30重量份，即所述UV可固化组合物为100重量份，而所述流变改性剂构成约0.1～约30份的额外重量。在其他实施方案中，与100重量份的UV可固化组合物相比，所述流变改性剂构成约0.1～约20重量份。在特定的另外的实施方案中，与100重量份的UV可固化组合物相比，所述流变改性剂构成约0.2～约10重量份。
所述抗微生物试剂通常选自醛、N-酰苯胺、双胍、银、银化合物、双酚、和季铵化合物。与100重量份的UV可固化组合物相比，所述抗微生物试剂通常存在的量为约0.5～约50重量份。在其他实施方案中，所述抗微生物试剂存在的量为所述组合物的约0.5～约30重量份。在某些另外的实施方案中，所述抗微生物试剂存在的量为约0.5～约20重量份。
所述抗微生物试剂可溶于所述UV可固化组合物中或均匀分布在其中。以这种方式，发现足够多的抗微生物试剂能够在所述组合物内迁移而接触到微生物活动的位置。无论如何，优选的是，所述抗微生物试剂不与所述组合物的其他成分发生化学反应。
所述UV涂料制剂能够为聚氨酯或聚酯型丙烯酸酯，例如：源自Electronic Materials Inc.(EMI)(EM Breckenridge，Co.)的7104、7101、7124-K、7105-5K；源自Dymax Corporation(Torrington，CT.)的1168-M、I-20781；源自Permabond Engineering Adhesives(Somerset，NJ)的UV 630。所述涂料的粘度应小于10000cps，优选小于5000cps，最优选20～1000cps。
实施例
实施例1
配制了本发明范围内的UV可固化组合物并按下表1中所述对其微生物杀灭率和抑制区域进行了试验。各种组合物基本上相同，除了抗微生物试剂按如下所述变化之外。所述组合物包含名称为EMI 7104的UV可固化组合物。所述UV可固化组合物由30～70％的低聚物、20～60％的单体、2～7％的光引发剂构成。添加到100份UV可固化组合物中的是得自Cabot且名称为Cabot′s MS-55的2.6份锻制二氧化硅。还添加的是7.2份的抗微生物试剂。用于所述制剂中的具体的抗微生物试剂如下：
试样#1.氯己定二乙酸盐
2.阿来西定
3.磺胺嘧啶银
4.醋酸银
5.柠檬酸银水合物
6.西曲溴铵
7.氯化十六烷基非那吡啶
8.苯扎氯铵
9.邻苯二甲醛
10.银元素
在三种(3)微生物试剂即表皮葡萄球菌(革兰氏阳性细菌)；铜绿假单胞菌(革兰氏阴性细菌)；和白色念珠菌(酵母或真菌)上对各种组合物进行了试验。将结果总结于表1中。
表1UV涂料1制剂的接触杀灭和抑制区域
Figure BDA0000075082000000091
ND-因之前100％的杀灭率而无数据
生长-微生物继续生长
各种组合物在杀灭细菌试剂方面通常是有效的。在一(1)小时时间内，除了含银元素的组合物之外，所有的组合物在杀灭白色念珠菌方面都是有效的。根据表1可见，氯化十六烷基非那吡啶和西曲溴铵比其他抗微生物试剂更有效。
实施例2
在这些实例中，将几种抗微生物试剂并入在本发明范围内的UV可固化的涂料组合物中。各种制剂包括100份的7104UV涂料、2.6份热解二氧化硅[名称为M-5]、和5.0份抗微生物试剂。在所述试验中包括银和氯己定，因为它们是在医疗技术中通常使用的抗微生物试剂。将这些试验的结果示于表2中。
表2UV制剂中选择的抗微生物试剂(5％的试剂)的接触杀灭和抑制区域
Figure BDA0000075082000000101
当使用7份抗微生物试剂时，获得了表3中所示的结果。
表3UV制剂中选择的抗微生物试剂(7％的试剂)的接触杀灭(％)和抑制区域(mm)
Figure BDA0000075082000000111
实施例3
在表4中，使用氯化十六烷基非那吡啶(制剂#1)作为抗微生物试剂制备了上述制剂。这种组合物在1分钟之内具有100％的接触杀灭。使用氯己定二乙酸盐作为试剂的同样制剂(制剂#4)在1小时内对所有三种微生物具有100％的接触杀灭。然而，两种常规组合物仅在约8小时之后才对选定的微生物具有100％的接触杀灭(两者都使用银化合物或银元素作为试剂)。
表4商购的制剂分析
Figure BDA0000075082000000121
(PC)1：氯化十六烷基非那吡啶作为试剂
(PC)4：氯己定二乙酸盐作为试剂
实施例4
表5显示，当使用表皮葡萄球菌作为微生物时，上述四种试剂能够在1小时内具有100％的接触杀灭且持续高达几乎4天。然而，常规的银试剂制剂从第1天开始就根本没有1小时接触杀灭。
表5对选定的抗微生物试剂进行盐水滤出速率试验(通过使用表皮葡萄球菌作为微生物的1小时接触杀灭)
  0小时   24小时   48小时   72小时   94小时
  1   100   100   100   100   100
  2   100   100   100   100   100
  3   100   100   100   100   100
  4   100   100   100   100   100
  5   0.0   1.96   0.0   0.0   0.0
  6   100   76.5   55.4   87.8   100
＊注释：
1.氯化十六烷基非那吡啶
2.西曲溴铵
3.苯扎氯铵
4.氯己定二乙酸盐
5.银
6.氯己定葡萄糖酸盐
实施例5
对上述组合物进行盐水滤出试验。根据表6可看出，当使用铜绿假单胞菌作为微生物时，氯己定葡萄糖酸盐在48小时之后明显失去了其1小时接触杀灭能力。然而，其他试剂看来保持了高达94小时的接触杀灭能力。
表6对选定的抗微生物试剂进行盐水滤出速率试验(通过使用铜绿假单胞菌作为微生物的1小时接触杀灭)
  0小时   24小时   48小时   72小时   94小时
  1   100   100   100   100   100
  2   100   100   100   100   100
  3   100   100   100   100   99.4
  4   100   100   100   100   100
  5   100   100   100   100   100
  6   100   96.0   96.5   1.2   0.0
＊注释：
1.氯化十六烷基非那吡啶
2.西曲溴铵
3.苯扎氯铵
4.氯己定二乙酸盐
5.银
6.氯己定葡萄糖酸盐
实施例6
根据表7中的数据可清楚看到，当使用白色念珠菌作为微生物时，两种常规制剂(银或氯己定葡萄糖酸盐)在24小时之后都明显失去了其功效。本文中试验的顶部四种试剂在高达94小时内具有100％的功效。
表7对选定的抗微生物试剂进行盐水滤出速率试验(通过使用白色念珠菌作为微生物的1小时接触杀灭)
  0小时   24小时   48小时   72小时   94小时
  1   100   100   100   100   100
  2   100   100   100   100   100
  3   100   100   100   100   100
  4   100   100   100   100   100
  5   95.2   97.6   62.4   30.0   39.7
  6   87.6   100   29.1   25.4   12.7
＊注释：
7.氯化十六烷基非那吡啶
8.西曲溴铵
9.苯扎氯铵
10.氯己定二乙酸盐
11.银
12.氯己定葡萄糖酸盐
实施例7
在该实施例中，制备了本发明范围内的几种制剂。使用通过EMI制造的各种专利制剂对所述UV可固化组合物进行了改变。测量了抗微生物活性并比较了断裂伸长率。数据如下：
表8断裂伸长率
Figure BDA0000075082000000151
Figure BDA0000075082000000152
Figure BDA0000075082000000153

Claims (23)

1.抗微生物紫外线(UV)可固化涂料，其包含：
包含低聚物、单体和光引发剂的UV可固化组合物；
流变改性剂；和
抗微生物试剂。
2.权利要求1的抗微生物UV可固化涂料，其中所述低聚物选自丙烯酸改性的脂族聚氨酯、丙烯酸改性的芳族聚氨酯、丙烯酸改性的聚酯、不饱和聚酯、丙烯酸改性的聚醚和丙烯酸改性的丙烯酸系材料。
3.权利要求2的抗微生物UV可固化涂料，其中所述丙烯酸改性的官能团选自单官能、二官能、三官能、四官能、五官能和六官能的丙烯酸酯。
4.权利要求1的抗微生物UV可固化涂料，其中所述单体选自丙烯酸2-乙基己基酯、丙烯酸异辛酯、丙烯酸异冰片酯、1，6-己二醇二丙烯酸酯、二甘醇二丙烯酸酯、三甘醇二丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇三丙烯酸酯、二甲氧基苯基苯乙酮己基甲基丙烯酸酯和1，6-己二醇甲基丙烯酸酯。
5.权利要求1的抗微生物UV可固化涂料，其中所述光引发剂选自苯偶姻醚、苯乙酮、苯甲酰基肟、酰基氧化膦和米蚩酮、噻吨酮、蒽醌(anthroguionone)、二苯甲酮、甲基二乙醇胺和2-N-丁氧基乙基-4-(二甲基氨基)苯甲酸盐以及它们的组合。
6.权利要求1的抗微生物UV可固化涂料，其中所述流变改性剂选自有机粘土、蓖麻蜡、聚酰胺蜡、聚氨酯和热解二氧化硅。
7.权利要求1的抗微生物UV可固化涂料，其中所述流变改性剂是热解二氧化硅。
8.权利要求1的抗微生物UV可固化涂料，其中所述抗微生物试剂选自醛、N-酰苯胺、双胍、银、银化合物、双酚和季铵化合物。
9.权利要求1的抗微生物UV涂料，其中所述抗微生物试剂选自西曲溴铵和氯化十六烷基非那吡啶。
10.权利要求1的抗微生物UV涂料，其中所述抗微生物试剂选自氯己定二乙酸盐、阿来西定和苯扎氯铵。
11.权利要求1的抗微生物UV可固化涂料，其中所述组合物以在100重量份所述UV可固化组合物中约0.1～约30重量份的量包含流变改性剂。
12.权利要求1的抗微生物UV可固化涂料，其中所述组合物以在100重量份所述UV可固化组合物中约0.2～约20重量份的量包含流变改性剂。
13.权利要求1的抗微生物UV可固化涂料，其中所述组合物以在100重量份所述UV可固化组合物中约0.2～约10重量份的量包含流变改性剂。
14.权利要求1的抗微生物UV可固化涂料，其中所述组合物以在100重量份所述UV可固化组合物中约0.5～约50重量份的量包含抗微生物试剂。
15.权利要求1的抗微生物UV可固化涂料，其中所述组合物以在100重量份所述UV可固化组合物中约0.5～约30重量份的量包含抗微生物试剂。
16.权利要求1的抗微生物UV可固化涂料，其中所述组合物以在100重量份所述UV可固化组合物中约0.5～约20重量份的量包含抗微生物试剂。
17.UV可固化涂料组合物，其包含：
a)UV可固化组合物，具有：
约10％～约90wt％的低聚物，所述低聚物选自丙烯酸改性的脂族聚氨酯、丙烯酸改性的芳族聚氨酯、丙烯酸改性的聚酯、不饱和聚酯、丙烯酸改性的聚醚和丙烯酸改性的丙烯酸系材料；
约5％～约90wt％的单体，所述单体选自丙烯酸2-乙基己基酯、丙烯酸异辛酯、丙烯酸异冰片酯、1，6-己二醇二丙烯酸酯、二甘醇二丙烯酸酯、三甘醇二丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇三丙烯酸酯、二甲氧基苯基苯乙酮己基甲基丙烯酸酯和1，6-己二醇甲基丙烯酸酯；
b)在100份UV可固化组合物中的约0.1～约30重量份的流变改性剂，所述流变改性剂选自有机粘土、蓖麻蜡、聚酰胺蜡、聚氨酯和热解二氧化硅；
c)在100份UV可固化组合物中的约0.5～约50重量份的抗微生物试剂，所述抗微生物试剂选自醛、N-酰苯胺、双胍、银、银化合物、双酚和季铵化合物；以及
d)约1～约10份的光引发剂。
18.抗微生物涂料，其包含：
具有低聚物、单体、光引发剂、流变改性剂的UV可固化组合物；和
抗微生物试剂，所述抗微生物试剂选自西曲溴铵、氯化十六烷基非那吡啶、氯己定二乙酸盐、阿来西定和苯扎氯铵。
19.权利要求17的抗微生物涂料，其中所述抗微生物试剂为阿来西定。
20.权利要求17的抗微生物涂料，其中所述抗微生物试剂是西曲溴铵和氯化十六烷基非那吡啶。
21.权利要求17的抗微生物涂料，其中所述抗微生物试剂是氯己定二乙酸盐。
22.权利要求17的抗微生物涂料，其中所述抗微生物试剂是苯扎氯铵。
23.权利要求17的抗微生物涂料，其还包括含热解二氧化硅的流变改性剂。
CN2009801542921A 2008-12-01 2009-11-25 抗微生物的uv可固化涂料组合物 Pending CN102272245A (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US11898808P 2008-12-01 2008-12-01
US61/118,988 2008-12-01
US12/397,760 US20100135949A1 (en) 2008-12-01 2009-03-04 Antimicrobial compositions
US12/397,760 2009-03-04
PCT/US2009/065941 WO2010065421A1 (en) 2008-12-01 2009-11-25 Antimicrobial uv curable coating compositions

Publications (1)

Publication Number Publication Date
CN102272245A true CN102272245A (zh) 2011-12-07

Family

ID=42223012

Family Applications (4)

Application Number Title Priority Date Filing Date
CN2009801542921A Pending CN102272245A (zh) 2008-12-01 2009-11-25 抗微生物的uv可固化涂料组合物
CN200980154281.3A Active CN102272274B (zh) 2008-12-01 2009-11-25 抗微生物润滑剂组合物
CN2009801542796A Pending CN102271826A (zh) 2008-12-01 2009-11-30 对医疗器材施涂抗微生物涂料的系统和方法
CN200980154283.2A Active CN102272244B (zh) 2008-12-01 2009-11-30 抗微生物溶剂涂料组合物

Family Applications After (3)

Application Number Title Priority Date Filing Date
CN200980154281.3A Active CN102272274B (zh) 2008-12-01 2009-11-25 抗微生物润滑剂组合物
CN2009801542796A Pending CN102271826A (zh) 2008-12-01 2009-11-30 对医疗器材施涂抗微生物涂料的系统和方法
CN200980154283.2A Active CN102272244B (zh) 2008-12-01 2009-11-30 抗微生物溶剂涂料组合物

Country Status (12)

Country Link
US (5) US20100135949A1 (zh)
EP (4) EP2370559B1 (zh)
JP (4) JP5615289B2 (zh)
KR (4) KR101691679B1 (zh)
CN (4) CN102272245A (zh)
AU (4) AU2009322693B2 (zh)
BR (4) BRPI0922357A2 (zh)
CA (4) CA2745194C (zh)
ES (3) ES2618803T3 (zh)
MX (4) MX336185B (zh)
WO (4) WO2010065421A1 (zh)
ZA (3) ZA201104198B (zh)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110938365A (zh) * 2018-09-25 2020-03-31 天津大学 一种水性聚氨酯抗菌涂料及其制备方法
CN110938359A (zh) * 2018-09-25 2020-03-31 天津大学 利用亲水性扩链剂提高聚氨酯涂料抗菌性能的方法
CN111955476A (zh) * 2020-09-03 2020-11-20 常熟理工学院 一种led光固化型农药微胶囊剂及其制备方法

Families Citing this family (81)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11229746B2 (en) 2006-06-22 2022-01-25 Excelsior Medical Corporation Antiseptic cap
US9078992B2 (en) 2008-10-27 2015-07-14 Pursuit Vascular, Inc. Medical device for applying antimicrobial to proximal end of catheter
US20100135949A1 (en) * 2008-12-01 2010-06-03 Becton, Dickinson And Company Antimicrobial compositions
US11219706B2 (en) 2009-03-11 2022-01-11 Arrow International Llc Enhanced formulations for coating medical devices
US8821455B2 (en) 2009-07-09 2014-09-02 Becton, Dickinson And Company Antimicrobial coating for dermally invasive devices
AU2011248537B2 (en) 2010-04-28 2014-04-17 University Of Georgia Research Foundation, Inc. Photochemical cross-linkable polymers, methods of marking photochemical cross-linkable polymers, methods of using photochemical cross-linkable polymers, and methods of making articles containing photochemical cross-linkable polymers
US20110301553A1 (en) * 2010-06-04 2011-12-08 Smiths Medical Asd, Inc. Antimicrobial lubricant
JP5639272B2 (ja) 2010-09-10 2014-12-10 ヘンケル・ユーエス・アイピー・リミテッド・ライアビリティ・カンパニーＨｅｎｋｅｌ ＵＳ ＩＰ ＬＬＣ 断熱性が改善された接着剤
US8257827B1 (en) 2011-06-02 2012-09-04 The Regents Of The University Of California Silicone composition and devices incorporating same
EP2731658B1 (en) 2011-07-12 2020-04-01 Pursuit Vascular, Inc. Device for delivery of antimicrobial agent into trans-dermal catheter
EP2739315A4 (en) * 2011-08-04 2015-04-29 Univ Georgia PERMANENT MOUNTING OF AMMONIUM AND GUANIDINE-BASED ANTIMICROBIAL ACTIVITIES ON SURFACES WITH C-H FUNCTIONALITY
KR20200044985A (ko) 2011-08-05 2020-04-29 메사추세츠 인스티튜트 오브 테크놀로지 액체 함침 표면, 이의 제조 방법 및 이것이 일체화된 장치
WO2013056007A2 (en) 2011-10-14 2013-04-18 University Of Georgia Research Foundation, Inc. Photochemical cross-linkable polymers, methods of making photochemical cross-linkable plolymers, methods of using photochemical cross-linkable poloymers, and methods of making articles containing photochemical cross-linkable polymers
EP2780051B1 (en) * 2011-11-09 2018-10-24 Arrow International, Inc. Novel enhanced formulations for coating medical devices
EP2828174A1 (en) 2012-03-23 2015-01-28 Massachusetts Institute of Technology Self-lubricating surfaces for food packaging and food processing equipment
JP5935133B2 (ja) * 2012-03-29 2016-06-15 フジコピアン株式会社 ハードコートフィルム
US20130255061A1 (en) * 2012-04-03 2013-10-03 Becton, Dickinson And Company Systems and methods for applying a novel antimicrobial coating material to a medical device
US9352119B2 (en) * 2012-05-15 2016-05-31 Becton, Dickinson And Company Blood control IV catheter with antimicrobial properties
US20130337027A1 (en) 2012-05-24 2013-12-19 Massachusetts Institute Of Technology Medical Devices and Implements with Liquid-Impregnated Surfaces
JP2015522839A (ja) * 2012-05-24 2015-08-06 マサチューセッツ インスティテュート オブ テクノロジー 液体含浸表面を有する装置
WO2014028203A1 (en) * 2012-08-14 2014-02-20 Henkel US IP LLC Moisture and vapor barrier coating compositions
US9579486B2 (en) 2012-08-22 2017-02-28 Becton, Dickinson And Company Blood control IV catheter with antimicrobial properties
KR101398301B1 (ko) * 2012-09-25 2014-05-27 주식회사 신바람 좁은 공간을 활용할 수 있는 다용도 수납형 문
US20140178611A1 (en) 2012-11-19 2014-06-26 Massachusetts Institute Of Technology Apparatus and methods employing liquid-impregnated surfaces
MX2015006238A (es) 2012-11-19 2015-12-03 Massachusetts Inst Technology Aparato y metodos que emplean superficies impregnadas con liquido.
AU2013359919A1 (en) 2012-12-11 2015-07-02 Nano Safe Coatings Incorporated (A Florida Corporation 3 P14000024914) UV cured benzophenone terminated quaternary ammonium antimicrobials for surfaces
US9803090B2 (en) * 2013-02-01 2017-10-31 Croda International Plc Self-disinfecting surfaces
US9695323B2 (en) 2013-02-13 2017-07-04 Becton, Dickinson And Company UV curable solventless antimicrobial compositions
US9750928B2 (en) 2013-02-13 2017-09-05 Becton, Dickinson And Company Blood control IV catheter with stationary septum activator
US9327095B2 (en) 2013-03-11 2016-05-03 Becton, Dickinson And Company Blood control catheter with antimicrobial needle lube
US9750927B2 (en) 2013-03-11 2017-09-05 Becton, Dickinson And Company Blood control catheter with antimicrobial needle lube
AU2014249274B2 (en) 2013-03-11 2016-11-24 Teleflex Medical Incorporated Devices with anti-thrombogenic and anti-microbial treatment
US20150027920A1 (en) * 2013-07-25 2015-01-29 Dennis Christopher Riordan Medicine cup with infection control tab
US8877882B1 (en) 2013-10-04 2014-11-04 Rochal Industries Llp Non-self-adherent coating materials
GB201322453D0 (en) * 2013-12-18 2014-02-05 Dow Corning Antifriction coating
US10792399B2 (en) 2014-02-20 2020-10-06 Becton, Dickinson And Company Antimicrobial inserts for medical devices
US10792398B2 (en) 2014-02-20 2020-10-06 Becton, Dickinson And Company Antimicrobial inserts for medical devices
SG10202007098SA (en) 2014-04-18 2020-08-28 Becton Dickinson Co Needle capture safety interlock for catheter
US9675793B2 (en) 2014-04-23 2017-06-13 Becton, Dickinson And Company Catheter tubing with extraluminal antimicrobial coating
US9789279B2 (en) 2014-04-23 2017-10-17 Becton, Dickinson And Company Antimicrobial obturator for use with vascular access devices
US10376686B2 (en) 2014-04-23 2019-08-13 Becton, Dickinson And Company Antimicrobial caps for medical connectors
US10149971B2 (en) 2014-04-23 2018-12-11 Becton, Dickinson And Company Antimicrobial stopcock medical connector
US20160008569A1 (en) * 2014-07-08 2016-01-14 Becton, Dickinson And Company Antimicrobial actuator for opening the side port of a ported catheter
US10232088B2 (en) * 2014-07-08 2019-03-19 Becton, Dickinson And Company Antimicrobial coating forming kink resistant feature on a vascular access device
US20160073937A1 (en) * 2014-09-11 2016-03-17 Becton, Dickinson And Company Blood sampling system for improving draw success and reducing hemolysis
KR101641857B1 (ko) * 2014-11-26 2016-07-22 삼화페인트공업주식회사 자외선 경화형 항균 도료 조성물
US10004890B2 (en) 2015-01-27 2018-06-26 Becton, Dickinson And Company Antimicrobial inserts for stopcock medical connectors
MX2017013349A (es) 2015-04-17 2018-03-01 Becton Dickinson Co Conjunto de cateter de seguridad para el control de la sangre de multiples usos.
CA2982456A1 (en) 2015-05-08 2016-11-17 Icu Medical, Inc. Medical connectors configured to receive emitters of therapeutic agents
JP6803382B2 (ja) * 2015-07-24 2020-12-23 テレフレックス メディカル インコーポレイテッド 外科的用途のための抗菌性組成物
EP3341358B1 (en) 2015-08-27 2023-03-08 Nano Safe Coatings Incorporated (a Florida Corporation 3 P 14000024914) Preparation of sulfonamide-containing antimicrobials and substrate treating compositions of sulfonamide-containing antimicrobials
US10493244B2 (en) 2015-10-28 2019-12-03 Becton, Dickinson And Company Extension tubing strain relief
EP3662966A1 (en) 2015-10-28 2020-06-10 Carefusion 303 Inc. Closed iv access device with y-port needle-free connector
KR101680003B1 (ko) 2016-01-26 2016-11-25 (주)한도기공 압출스크류와 압출다이의 대칭 결합 구조를 갖는 혼련용 자동 믹싱롤
DE102016108198A1 (de) * 2016-05-03 2017-11-09 B. Braun Avitum Ag Medizintechnisches Gerät mit antimikrobieller Oberflächenbeschichtung sowie Verfahren zur Bekämpfung von Mikroorganismen auf der Oberfläche eines solchen Geräts
SI3525865T1 (sl) 2016-10-14 2023-01-31 Icu Medical, Inc. Razkuževalni pokrovčki za medicinske konektorje
WO2018136274A1 (en) * 2017-01-20 2018-07-26 Medivators Inc. Disposable valve for an endoscope having a lubricant and/or antimicrobial
USD852368S1 (en) 2017-03-27 2019-06-25 Avery Dennison Corporation Catheter dressing
WO2018204206A2 (en) 2017-05-01 2018-11-08 Icu Medical, Inc. Medical fluid connectors and methods for providing additives in medical fluid lines
US10543354B2 (en) 2017-09-27 2020-01-28 Becton, Dickinson And Company Peripheral intravenous catheters having flow diverting features
KR102193014B1 (ko) * 2017-10-11 2020-12-18 주식회사 엘지화학 항균성 고분자 코팅 조성물 및 항균성 고분자 필름
US10994101B2 (en) * 2018-03-02 2021-05-04 Becton, Dickinson And Company Catheter assembly with high viscosity lubricant and related methods
KR102112057B1 (ko) * 2018-07-13 2020-05-18 (주)유니드 항균성, 항곰팡이성 및 고기능성 코팅액 조성물 및 이를 이용한 제품
US11613719B2 (en) 2018-09-24 2023-03-28 Becton, Dickinson And Company Self-lubricating medical articles
US11541221B2 (en) 2018-11-07 2023-01-03 Icu Medical, Inc. Tubing set with antimicrobial properties
US11534595B2 (en) 2018-11-07 2022-12-27 Icu Medical, Inc. Device for delivering an antimicrobial composition into an infusion device
US11517732B2 (en) 2018-11-07 2022-12-06 Icu Medical, Inc. Syringe with antimicrobial properties
US11541220B2 (en) 2018-11-07 2023-01-03 Icu Medical, Inc. Needleless connector with antimicrobial properties
US11400195B2 (en) 2018-11-07 2022-08-02 Icu Medical, Inc. Peritoneal dialysis transfer set with antimicrobial properties
JP6838037B2 (ja) * 2018-11-16 2021-03-03 イビデン株式会社 抗ウィルス性硬化物の固着方法および抗ウィルス性部材の製造方法
CA3118905A1 (en) 2018-11-21 2020-05-28 Icu Medical, Inc. Antimicrobial device comprising a cap with ring and insert
CN110041199B (zh) * 2019-01-23 2021-07-09 中山大学 一种含邻苯二甲醛的单体、由单体制备的聚合物及制备方法和应用
KR102636596B1 (ko) * 2019-01-31 2024-02-13 주식회사 엘지화학 항균성 고분자 코팅 조성물 및 항균성 고분자 필름
KR102557941B1 (ko) * 2019-03-11 2023-07-19 주식회사 엘지화학 항균성 고분자 코팅 조성물 및 항균성 고분자 필름
US11648385B2 (en) 2019-05-30 2023-05-16 Beeton, Dickinson and Company Automatic disinfection of a vascular access device connector
KR102450967B1 (ko) * 2019-12-06 2022-10-05 울산대학교 산학협력단 항균 및 탈취용 유무기 에멀젼 조성물 및 이를 포함하는 섬유 매트
CN111282777B (zh) * 2020-03-26 2022-07-12 苏州微比特自动化有限公司 一种涂覆固化产线
US11730862B2 (en) * 2020-05-08 2023-08-22 DePuy Synthes Products, Inc. Identifier-based application of therapeutic coatings to medical implant devices
CA3204371A1 (en) 2020-12-07 2022-06-16 Icu Medical, Inc. Peritoneal dialysis caps, systems and methods
CN113694226A (zh) * 2021-08-20 2021-11-26 中山大学 一种紫外杀菌缓蚀剂协同杀菌消毒和抗生物附着的方法
CN115340901A (zh) * 2022-09-22 2022-11-15 袁培锷 生物润滑剂组合物及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020040092A1 (en) * 1997-01-28 2002-04-04 Stepan Company Antimicrobial polymer latexes derived from unsaturated quaternary ammonium compounds and antimicrobial coatings, sealant, adhesives and elastomers produced from such latexes
CN1487035A (zh) * 2002-08-07 2004-04-07 珠海东诚化工有限公司 紫外光固化的绝缘涂料
CN1526771A (zh) * 2003-03-03 2004-09-08 珠海东诚化工有限公司 可见光固化金属涂料
US20070275101A1 (en) * 2006-02-23 2007-11-29 Lu Helen S Removable antimicrobial coating compositions and methods of use

Family Cites Families (138)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223629A (en) * 1963-05-13 1965-12-14 Shell Oil Co Lubricant compositions
US3986508A (en) * 1973-08-22 1976-10-19 Abcor, Inc. Sterilizable, medical connector for blood processing
US4359564A (en) 1980-03-14 1982-11-16 Rohm & Haas Co. Addition polymer of oligomeric polyesters of acrylic acid
US4339336A (en) * 1981-03-23 1982-07-13 Texaco Inc. Quaternary ammonium succinimide salt composition and lubricating oil containing same
US4512766A (en) * 1982-12-08 1985-04-23 Whitman Medical Corporation Catheter valve
US4716032A (en) * 1983-08-03 1987-12-29 Geoffrey J. Westfall Aerosol spray composition for mastitis prevention
JPH0696522B2 (ja) * 1983-10-24 1994-11-30 ロクリ− サ−ヴイシズ プロプライエタリ− リミテツド 起泡型生物致死組成物
US4584192A (en) * 1984-06-04 1986-04-22 Minnesota Mining & Manufacturing Company Film-forming composition containing an antimicrobial agent and methods of use
US4677143A (en) * 1984-10-01 1987-06-30 Baxter Travenol Laboratories, Inc. Antimicrobial compositions
DE3502594A1 (de) * 1985-01-26 1986-07-31 Etablissement Dentaire Ivoclar, Schaan Roentgenopaker dentalwerkstoff
US4642126A (en) * 1985-02-11 1987-02-10 Norton Company Coated abrasives with rapidly curable adhesives and controllable curvature
US4629743A (en) * 1985-05-20 1986-12-16 The B.F. Goodrich Company Process for preparing high bulk density vinyl resins
IL78826A (en) * 1986-05-19 1991-05-12 Yissum Res Dev Co Precursor composition for the preparation of a biodegradable implant for the sustained release of an active material and such implants prepared therefrom
US6051609A (en) * 1997-09-09 2000-04-18 Tristrata Technology, Inc. Additives enhancing the effect of therapeutic agents
DE3800094C2 (de) * 1987-01-14 1998-05-14 Ciba Geigy Ag Verfahren und hydrophobe Zubereitung zur Bekämpfung von Schnittwundparasiten bei Pflanzen
US5019096A (en) * 1988-02-11 1991-05-28 Trustees Of Columbia University In The City Of New York Infection-resistant compositions, medical devices and surfaces and methods for preparing and using same
US5013717A (en) 1988-04-18 1991-05-07 Becton, Dickinson And Company Blood compatible, lubricious article and composition and method therefor
CA1331333C (en) * 1988-07-20 1994-08-09 Thomas M. Gentle Antimicrobial antifoam compositions and methods
US4933178A (en) * 1988-10-07 1990-06-12 Biointerface Technologies, Inc. Metal-based antimicrobial coating
US4925668A (en) * 1989-01-18 1990-05-15 Becton, Dickinson And Company Anti-infective and lubricious medical articles and method for their preparation
DE4011867A1 (de) 1990-04-12 1991-10-17 Herberts Gmbh Leitfaehige, strahlenhaertbare lacke
US5077352A (en) * 1990-04-23 1991-12-31 C. R. Bard, Inc. Flexible lubricious organic coatings
US5773487A (en) * 1991-05-15 1998-06-30 Uv Coatings, Inc. Finishing composition which is curable by UV light and method of using same
JP2666654B2 (ja) 1992-04-01 1997-10-22 住友金属工業株式会社 鋼材への水溶性防錆油の塗付方法
TW227518B (zh) * 1992-06-30 1994-08-01 Toa Gosei Chem Ind
DE4312656C2 (de) * 1993-04-19 1996-01-25 Beiersdorf Ag Kühlend wirkende kosmetische oder dermatologische Zusammensetzungen
JPH0751651A (ja) * 1993-08-19 1995-02-28 Mitsubishi Materials Corp 汚れ防止かつ消臭用被覆材
US5547662A (en) * 1993-08-27 1996-08-20 Becton, Dickinson And Company Preparation of a skin surface for a surgical procedure
US5512199A (en) * 1993-11-02 1996-04-30 Becton Dickinson And Company Hand wipe solution
CA2151774C (en) * 1994-06-27 1999-04-06 Minh Quang Hoang Skin disinfecting formulations
JPH08209064A (ja) 1994-12-27 1996-08-13 Ebihara:Kk 天然木化粧合板用抗菌塗料
US6413539B1 (en) * 1996-10-31 2002-07-02 Poly-Med, Inc. Hydrogel-forming, self-solvating absorbable polyester copolymers, and methods for use thereof
JPH08311373A (ja) * 1995-05-22 1996-11-26 Tokuyama Corp 抗菌性被膜用光硬化性組成物
US5772640A (en) * 1996-01-05 1998-06-30 The Trustees Of Columbia University Of The City Of New York Triclosan-containing medical devices
US6503952B2 (en) * 1995-11-13 2003-01-07 The Trustees Of Columbia University In The City Of New York Triple antimicrobial composition
JPH09151262A (ja) 1995-11-29 1997-06-10 Fuji Silysia Chem Ltd 表面硬化樹脂板
JPH09157548A (ja) 1995-12-01 1997-06-17 Sumitomo Chem Co Ltd 抗菌性の表面コート剤および合成樹脂成形体
US6576633B1 (en) * 1996-02-22 2003-06-10 The Dow Chemical Company Stable liquid antimicrobial suspension compositions containing quarternaries prepared from hexamethylenetetramine and certain halohydrocarbons
EP0860213A3 (de) * 1997-01-03 2002-10-16 Therapol SA Bioaktive Beschichtung von Oberflächen
US6084005A (en) * 1997-02-24 2000-07-04 Kuraray Co., Ltd. Antimicrobial caries-detecting composition
EP0991702B2 (en) 1997-06-20 2017-07-19 Coloplast A/S A hydrophilic coating
US6110483A (en) * 1997-06-23 2000-08-29 Sts Biopolymers, Inc. Adherent, flexible hydrogel and medicated coatings
DE59802860D1 (de) * 1997-10-18 2002-02-28 Ddg Dental Devices Gmbh Desinfektionsmittel
WO1999032168A1 (en) 1997-12-22 1999-07-01 Becton Dickinson And Company A material for use in medical devices with a self-replenishing antimicrobial and/or lubricious surface
US6127320A (en) * 1998-01-19 2000-10-03 University Of Cincinnati Methods and compositions for increasing lubricity of rubber surfaces
US20020022660A1 (en) * 1998-01-20 2002-02-21 Hanuman B. Jampani Deep penetrating antimicrobial compositions
WO1999042079A2 (en) * 1998-02-19 1999-08-26 Oraceutical, Llc Antimicrobial denture adhesive composition
US6726899B2 (en) * 1998-09-24 2004-04-27 Advantage Dental Products, Inc. Calcified tissue facing preparation containing antimicrobial agent
US6299980B1 (en) * 1998-09-29 2001-10-09 Medtronic Ave, Inc. One step lubricious coating
JP2000178475A (ja) 1998-12-15 2000-06-27 Nisseki Kk 抗菌消臭性コ―ティング剤
JP3824120B2 (ja) * 1999-03-18 2006-09-20 新東工業株式会社 抗菌性を有する光重合性モノマー組成物、ならびに抗菌性を有する無溶剤タイプの紫外線および電子線硬化樹脂組成物
US6156373A (en) 1999-05-03 2000-12-05 Scimed Life Systems, Inc. Medical device coating methods and devices
US6706022B1 (en) 1999-07-27 2004-03-16 Alaris Medical Systems, Inc. Needleless medical connector with expandable valve mechanism
US7384895B2 (en) * 1999-08-16 2008-06-10 Ecolab Inc. Conveyor lubricant, passivation of a thermoplastic container to stress cracking and thermoplastic stress crack inhibitor
JP2001072438A (ja) 1999-08-31 2001-03-21 Wako Kagaku Kogyo Kk 抗菌性加工板硝子材
US6326417B1 (en) * 1999-10-21 2001-12-04 Jeneric/Pentron Incorporated Anti-microbial dental compositions and method
US6353041B1 (en) * 1999-10-22 2002-03-05 Kerr Corporation Dental compositions
US6310013B1 (en) * 1999-10-27 2001-10-30 Ecolab Inc. Lubricant compositions having antimicrobial properties and methods for manufacturing and using lubricant compositions having antimicrobial properties
AUPQ419099A0 (en) * 1999-11-23 1999-12-16 Ko, Thomas Sai Ying Novel compositions and methods
DK1106627T3 (da) * 1999-12-08 2004-02-23 Ciba Sc Holding Ag Hidtil ukendte fotoinitiatorsystem af phosphinoxider og hærdbare sammensætninger med lav farve
US7179849B2 (en) * 1999-12-15 2007-02-20 C. R. Bard, Inc. Antimicrobial compositions containing colloids of oligodynamic metals
EP1272152B1 (en) * 2000-04-03 2012-03-07 CHX Technologies Inc. Use of chlorhexidine in the prevention of root caries
US6861060B1 (en) * 2000-04-21 2005-03-01 Elena Luriya Personal care formulations
EP1164171A3 (en) * 2000-06-12 2002-04-24 General Electric Company Silicone compositions
US6699221B2 (en) * 2000-06-15 2004-03-02 Vincent L. Vaillancourt Bloodless catheter
AU2001281304B2 (en) * 2000-08-15 2006-05-25 Surmodics, Inc. Medicament incorporation matrix
US7329412B2 (en) * 2000-12-22 2008-02-12 The Trustees Of Columbia University In The City Of New York Antimicrobial medical devices containing chlorhexidine free base and salt
US6814085B2 (en) * 2000-12-29 2004-11-09 Steven J. Brattesani Dental floss with usage identification capability
KR100405030B1 (ko) 2001-02-10 2003-11-10 주식회사 유레이 신규 ｕｖ 경화형 항균제
JP3730529B2 (ja) 2001-03-27 2006-01-05 日本ペイント株式会社 多孔質素材の塗装方法及びその装置
FR2823113B1 (fr) * 2001-04-06 2005-12-16 Oreal Composition cosmetique anti-rides a effet immediat a base de dispersion aqueuse d'au moins une charge minerale
ATE438418T1 (de) * 2001-05-01 2009-08-15 Av Topchiev Inst Petrochemical Hydrogel-zusammensetzungen
FR2826292B1 (fr) * 2001-06-22 2004-01-23 Rhodia Chimie Sa Emulsions huile dans huile comprenant une silicone, dispersions de telles emulsions et utilisation
ITMI20011411A1 (it) * 2001-07-04 2003-01-04 Lafabrica S R L Metodo per proteggere un materiale per pavimentazione o rivestimento da sostanze macchianti
DE10139574A1 (de) * 2001-08-10 2003-02-20 Creavis Tech & Innovation Gmbh Erhalt des Lotus-Effektes durch Verhinderung des Mikrobenwachstums auf selbstreinigenden Oberflächen
DE10144531B4 (de) 2001-09-11 2006-01-19 Henkel Kgaa UV-härtende anti-fingerprint Beschichtungen, Verfahren zum Beschichten und Verwendung eines lösmittelfreien Überzugsmittels
DE60239140D1 (de) * 2001-10-10 2011-03-24 Microban Products Co Antimikrobielle strahlungshärtbare beschichtung
WO2003064412A1 (en) 2002-01-31 2003-08-07 Micro Science Tech Co., Ltd. Monomer with anti-microbial character, polymer using the same, and manufacturing method thereof
NO320324B1 (no) 2002-03-26 2005-11-21 Jotun As Polymerer og monomerer og anvendelse derav samt fremgangsmate for fremstilling av polymerer og begroingshindrende maling inneholdende polymerer
US20040147671A1 (en) * 2002-05-15 2004-07-29 Richard Milic Decorative coating composition for solid substrates
JP2003342402A (ja) 2002-05-27 2003-12-03 Mitsubishi Rayon Co Ltd 耐擦傷性を有する抗菌性樹脂成形品およびその製造方法
US6924325B2 (en) * 2002-06-21 2005-08-02 Kerr Corporation Silver-containing dental composition
JP2004043669A (ja) 2002-07-12 2004-02-12 Dainippon Toryo Co Ltd 粉体塗料の調色方法
ITMI20022072A1 (it) * 2002-10-01 2004-04-02 Lafabrica S R L Metodo per la decorazione di un substrato ceramico poroso ed in particolare del gres porcellanato levigato.
US20040115477A1 (en) * 2002-12-12 2004-06-17 Bruce Nesbitt Coating reinforcing underlayment and method of manufacturing same
FR2849444B1 (fr) * 2002-12-30 2006-07-28 Rhodia Chimie Sa Procede de preparation d'un suspension de silice dans une matiere silicone eventuellement reticulable
US20050048005A1 (en) * 2003-08-26 2005-03-03 Stockel Richard F. Antimicrobial compositions for dental applications
JP2005028209A (ja) 2003-07-07 2005-02-03 Dainippon Ink & Chem Inc 抗菌性、防かび性を有する硬化皮膜及びその形成方法
US20070000407A1 (en) * 2003-10-09 2007-01-04 York International Corporation Nano composite photocatalytic coating
WO2005037338A1 (en) * 2003-10-14 2005-04-28 Cook Incorporated Hydrophilic coated medical device
US7074839B2 (en) * 2004-03-01 2006-07-11 3M Innovative Properties Company Crosslinkable hydrophilic materials from reactive oligomers having pendent photoinitiator groups
US7232540B2 (en) * 2004-05-02 2007-06-19 Ashland Licensing And Intellectual Property Llc Radiation-curable coatings for plastic substrates from multifunctional acrylate oligomers
CA2565060A1 (en) * 2004-05-02 2005-11-17 Ashland Licensing And Intellectual Property Llc Radiation-curable coatings for metal substrates from multifunctional acrylate oligomers
DE102004039409A1 (de) * 2004-08-13 2006-02-23 Holmenkol Sport-Technologies Gmbh & Co. Kg Gleitmittel für Sportgeräte
US9028852B2 (en) * 2004-09-07 2015-05-12 3M Innovative Properties Company Cationic antiseptic compositions and methods of use
WO2006036967A1 (en) 2004-09-28 2006-04-06 Atrium Medical Corporation Solubilizing a drug for use in a coating
US9737637B2 (en) 2004-11-29 2017-08-22 Dsm Ip Assets B.V. Method for reducing the amount of migrateables of polymer coatings
JP2008527117A (ja) 2005-01-17 2008-07-24 ナノン アクティーゼルスカブ ポリマー含有被覆物によってポリマー表面を被覆する方法、およびポリマー被覆ポリマーを含む物品
US7498367B2 (en) * 2005-02-21 2009-03-03 Kerr Corporation Acid-tolerant dental composition
WO2006095648A1 (ja) * 2005-03-05 2006-09-14 Kyoto University ３次元フォトニック結晶及びその製造方法
CA2599667C (en) * 2005-03-10 2014-12-16 3M Innovative Properties Company Antimicrobial compositions comprising esters of hydroxy carboxylic acids
KR20070113284A (ko) * 2005-03-10 2007-11-28 쓰리엠 이노베이티브 프로퍼티즈 캄파니 미생물 오염의 감소방법
FR2884170B1 (fr) * 2005-04-08 2007-10-12 Rhodia Chimie Sa Utilisation d'une composition a base de siloxane destinee au moulage-demoulage de pneumatiques
WO2006116213A2 (en) * 2005-04-22 2006-11-02 Karrie Ann Sancho Antimicrobial spray for use on pets
US7651990B2 (en) * 2005-06-13 2010-01-26 3M Innovative Properties Company Foamable alcohol compositions comprising alcohol and a silicone surfactant, systems and methods of use
JP2007016096A (ja) 2005-07-06 2007-01-25 Chugoku Marine Paints Ltd 硬化性組成物、コーティング用組成物、塗料、防汚塗料、その硬化物、並びに基材の防汚方法
EP1922053B1 (en) * 2005-08-10 2014-11-19 DENTSPLY International Inc. Methods for preparing chair-side dental crowns
US8343523B2 (en) * 2005-08-22 2013-01-01 Quick-Med Technologies, Inc. Disinfectant with durable activity based on alcohol-soluble quaternary ammonium polymers and copolymers
US20070048344A1 (en) * 2005-08-31 2007-03-01 Ali Yahiaoui Antimicrobial composition
DE102005050186A1 (de) * 2005-10-18 2007-04-19 Dreve Otoplastik Gmbh Niedrigviskose, strahlungshärtbare Formulierung zur Herstellung von Ohrpassstücken mit antimikrobiellen Eigenschaften
US8227050B1 (en) 2005-10-31 2012-07-24 E I Du Pont De Nemours And Company Coating composition and method for coating substrates
US8017687B2 (en) * 2005-11-15 2011-09-13 Momentive Performance Materials Inc. Swollen silicone composition and process of producing same
US7863361B2 (en) * 2005-11-15 2011-01-04 Momentive Performance Materials Inc. Swollen silicone composition, process of producing same and products thereof
WO2007070440A2 (en) * 2005-12-09 2007-06-21 Pliant Corporation Selectively permeable films
US7896650B2 (en) * 2005-12-20 2011-03-01 3M Innovative Properties Company Dental compositions including radiation-to-heat converters, and the use thereof
US7462401B2 (en) * 2005-12-23 2008-12-09 Xerox Corporation Radiation curable composition
US20070160547A1 (en) * 2006-01-11 2007-07-12 Janet Duffy Method of applying a composition
US20070166344A1 (en) * 2006-01-18 2007-07-19 Xin Qu Non-leaching surface-active film compositions for microbial adhesion prevention
MX2008010504A (es) 2006-02-14 2009-03-31 Allegiance Corp Aplicador de liquido y metodo para reducir la concentracion de subproductos de antiseptico.
US8623446B2 (en) * 2006-02-25 2014-01-07 Metascape Llc Ultraviolet activated antimicrobial surfaces
KR20090003267A (ko) * 2006-02-28 2009-01-09 벡톤 디킨슨 앤드 컴퍼니 카테테르 잠금을 위한 항미생물성 조성물 및 방법
US8512294B2 (en) * 2006-07-28 2013-08-20 Becton, Dickinson And Company Vascular access device antimicrobial materials and solutions
US20100113871A1 (en) 2006-09-13 2010-05-06 Aylvin Jorge Angelo Athanasius Dias Antimicrobial coating
US8026297B2 (en) * 2007-01-29 2011-09-27 Bisco, Inc. Dental primer adhesive system and optional hydrophobic resin
EP2136645B1 (en) 2007-04-18 2013-06-19 Basf Se Antimicrobial plastics and coatings
JP2010531156A (ja) 2007-04-25 2010-09-24 ビーエーエスエフ ソシエタス・ヨーロピア 殺生性被膜を有する基材
US8052829B2 (en) * 2007-10-26 2011-11-08 Dymax Corporation Photopolymerizable compositions containing an oxonol dye
CN101925837B (zh) * 2007-11-30 2013-01-30 康宁股份有限公司 用于duv元件的致密均匀氟化物膜及其制备方法
US8048471B2 (en) * 2007-12-21 2011-11-01 Innovatech, Llc Marked precoated medical device and method of manufacturing same
US20090176907A1 (en) * 2008-01-08 2009-07-09 Ramesh Subramanian Direct-to-metal radiation curable compositions
WO2009097478A1 (en) * 2008-01-30 2009-08-06 Building Solutions Ip Company, Llc Ultraviolet cured coating system
US8034455B2 (en) 2008-06-06 2011-10-11 Novasolar Holdings Limited Coating composition, substrates coated therewith and methods of making and using same
US8178120B2 (en) * 2008-06-20 2012-05-15 Baxter International Inc. Methods for processing substrates having an antimicrobial coating
US8277826B2 (en) * 2008-06-25 2012-10-02 Baxter International Inc. Methods for making antimicrobial resins
CN101353545B (zh) 2008-08-26 2010-06-23 苏州市明大高分子科技材料有限公司 紫外光固化抗菌涂料及其制备方法
US20100135949A1 (en) 2008-12-01 2010-06-03 Becton, Dickinson And Company Antimicrobial compositions
US8821455B2 (en) * 2009-07-09 2014-09-02 Becton, Dickinson And Company Antimicrobial coating for dermally invasive devices
US20110065798A1 (en) 2009-09-17 2011-03-17 Becton, Dickinson And Company Anti-infective lubricant for medical devices and methods for preparing the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020040092A1 (en) * 1997-01-28 2002-04-04 Stepan Company Antimicrobial polymer latexes derived from unsaturated quaternary ammonium compounds and antimicrobial coatings, sealant, adhesives and elastomers produced from such latexes
CN1487035A (zh) * 2002-08-07 2004-04-07 珠海东诚化工有限公司 紫外光固化的绝缘涂料
CN1526771A (zh) * 2003-03-03 2004-09-08 珠海东诚化工有限公司 可见光固化金属涂料
US20070275101A1 (en) * 2006-02-23 2007-11-29 Lu Helen S Removable antimicrobial coating compositions and methods of use

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110938365A (zh) * 2018-09-25 2020-03-31 天津大学 一种水性聚氨酯抗菌涂料及其制备方法
CN110938359A (zh) * 2018-09-25 2020-03-31 天津大学 利用亲水性扩链剂提高聚氨酯涂料抗菌性能的方法
CN111955476A (zh) * 2020-09-03 2020-11-20 常熟理工学院 一种led光固化型农药微胶囊剂及其制备方法

Also Published As

Publication number Publication date
CN102272244A (zh) 2011-12-07
BRPI0922699A2 (pt) 2018-08-28
ES2643600T3 (es) 2017-11-23
US20100136209A1 (en) 2010-06-03
JP6022771B2 (ja) 2016-11-09
MX2011005738A (es) 2011-08-17
EP2370525A1 (en) 2011-10-05
CN102272274A (zh) 2011-12-07
KR101691678B1 (ko) 2016-12-30
WO2010065445A1 (en) 2010-06-10
KR20110100247A (ko) 2011-09-09
ES2701624T3 (es) 2019-02-25
BRPI0922697A2 (pt) 2018-08-28
ZA201104198B (en) 2012-02-29
JP2012510559A (ja) 2012-05-10
CA2745158A1 (en) 2010-06-10
MX336185B (es) 2016-01-11
JP2012510339A (ja) 2012-05-10
CA2745149C (en) 2017-01-03
AU2009322644A1 (en) 2011-06-23
KR20110100248A (ko) 2011-09-09
US20100135949A1 (en) 2010-06-03
KR20110099293A (ko) 2011-09-07
CA2745191A1 (en) 2010-06-10
WO2010065422A1 (en) 2010-06-10
AU2009322694B2 (en) 2016-04-21
MX2011005729A (es) 2011-07-29
WO2010065463A2 (en) 2010-06-10
US8426348B2 (en) 2013-04-23
MX2011005739A (es) 2011-07-29
AU2009322693A1 (en) 2011-06-23
JP5628195B2 (ja) 2014-11-19
CA2745191C (en) 2017-01-03
JP5730213B2 (ja) 2015-06-03
CA2745194C (en) 2017-05-09
EP2370526A1 (en) 2011-10-05
US20100137472A1 (en) 2010-06-03
US8754020B2 (en) 2014-06-17
MX349482B (es) 2017-07-28
MX2011005730A (es) 2011-07-29
BRPI0922354A2 (pt) 2018-05-29
BRPI0922354B1 (pt) 2020-09-15
JP5615289B2 (ja) 2014-10-29
US20130330387A1 (en) 2013-12-12
US20100137379A1 (en) 2010-06-03
CN102271826A (zh) 2011-12-07
AU2009322626B2 (en) 2015-06-25
JP2012510560A (ja) 2012-05-10
CN102272274B (zh) 2015-04-08
BRPI0922357A2 (pt) 2018-05-29
EP2370559B1 (en) 2018-09-12
AU2009322693B2 (en) 2015-01-29
JP2012510367A (ja) 2012-05-10
CN102272244B (zh) 2014-08-27
EP2370526B1 (en) 2017-07-12
CA2745194A1 (en) 2010-06-10
ES2618803T3 (es) 2017-06-22
ZA201104197B (en) 2012-02-29
EP2370559A1 (en) 2011-10-05
EP2370525B1 (en) 2017-01-25
US8691887B2 (en) 2014-04-08
ZA201104282B (en) 2012-02-29
KR101691679B1 (ko) 2016-12-30
WO2010065421A1 (en) 2010-06-10
EP2370210A2 (en) 2011-10-05
WO2010065463A3 (en) 2010-11-04
AU2009322694A1 (en) 2011-06-23
CA2745149A1 (en) 2010-06-10
KR20110106328A (ko) 2011-09-28
AU2009322626A1 (en) 2011-06-23

Similar Documents

Publication Publication Date Title
CN102272245A (zh) 抗微生物的uv可固化涂料组合物
US9695323B2 (en) UV curable solventless antimicrobial compositions

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C12 Rejection of a patent application after its publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20111207