US20100135949A1 - Antimicrobial compositions - Google Patents
Antimicrobial compositions Download PDFInfo
- Publication number
- US20100135949A1 US20100135949A1 US12/397,760 US39776009A US2010135949A1 US 20100135949 A1 US20100135949 A1 US 20100135949A1 US 39776009 A US39776009 A US 39776009A US 2010135949 A1 US2010135949 A1 US 2010135949A1
- Authority
- US
- United States
- Prior art keywords
- antimicrobial
- parts
- coating
- weight
- curable
- 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.)
- Abandoned
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- 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
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- 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
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- 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
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- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
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- 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
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- 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
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- 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
Definitions
- the present invention relates to antimicrobial compositions and methods for use of those compositions in various medical applications.
- One of the major challenges of modern medical treatment is control of infection and the spread of microbial organisms.
- Infusion therapy is one of the most common health care procedures. Hospitalized, home care, and other patients receive fluids, pharmaceuticals, and blood products via a vascular access device inserted into the vascular system. Infusion therapy may be used to treat an infection, provide anesthesia or analgesia, provide nutritional support, treat cancerous growths, maintain blood pressure and heart rhythm, or many other clinically significant uses.
- vascular access device may access a patient's peripheral or central vasculature.
- the vascular access device may be indwelling for short term (days), moderate term (weeks), or long term (months to years).
- the vascular access device may be used for continuous infusion therapy or for intermittent therapy.
- a common vascular access device is a plastic catheter that is inserted into a patient's vein.
- the catheter length may vary from a few centimeters for peripheral access, to many centimeters for central access and may included devices such as peripherally inserted central catheters (PICC).
- PICC peripherally inserted central catheters
- the catheter may be inserted transcutaneously or may be surgically implanted beneath the patient's skin.
- the catheter, or any other vascular access device attached thereto, may have a single lumen or multiple lumens for infusion of many fluids simultaneously.
- the vascular access device commonly includes a Luer adapter to which other medical devices may be attached.
- an administration set may be attached to a vascular access device at one end and an intravenous (IV) bag at the other.
- the administration set is a fluid conduit for the continuous infusion of fluids and pharmaceuticals.
- an IV access device is a vascular access device that may be attached to another vascular access device, closes the vascular access device, and allows for intermittent infusion or injection of fluids and pharmaceuticals.
- An IV access device may include a housing and a septum for closing the system. The septum may be opened with a blunt cannula or a male Luer of a medical device.
- CBSI catheter related blood stream infection
- CVC central venous catheter
- a vascular access device may serve as a nidus of infection, resulting in a disseminated BSI (blood stream infection). This may be caused by failure to regularly flush the device, a non-sterile insertion technique, or by pathogens that enter the fluid flow path through either end of the path subsequent to catheter insertion.
- BSI blood stream infection
- pathogens adhere to the vascular access device, colonize, and form a biofilm.
- the biofilm is resistant to most biocidal agents and provides a replenishing source for pathogens to enter a patient's bloodstream and cause a BSI.
- devices with antimicrobial properties are needed.
- One approach to preventing biofilm formation and patient infection is to provide an antimicrobial coating on various medical devices and components.
- Many medical devices are made with either metallic or polymeric materials. These materials usually have a high coefficient of friction.
- a low molecular weight material or liquid with a low coefficient of friction is usually compounded into the bulk of the materials or coated onto the surface of the substrates to help the functionality of the devices.
- thermoplastic polyurethane solution As the carrier for antimicrobial coatings.
- the solvent is usually tetrahydrofuran (THF), dimethylformamide (DMF), or a blend of both. Because THF can be oxidized very quickly and tends to be very explosive, an expensive explosion-proof coating facility is necessary.
- THF tetrahydrofuran
- DMF dimethylformamide
- SBR styrene-butadiene rubber
- One of the most commonly used antimicrobial agents used in coating medical device is silver.
- Silver salts and silver element are well known antimicrobial agents in both the medical surgical industry and general industries. They are usually incorporated into the polymeric bulk material or coated onto the surface of the medical devices by plasma, heat evaporation, electroplating, or by conventional solvent coating technologies. These technologies are tedious, expensive, and not environmentally friendly.
- the performance of silver coated medical devices is mediocre at best. For example, it can take up to eight (8) hours before the silver ion, ionized from the silver salts or silver element, to reach efficacy as an antimicrobial agent. As a result, substantial microbial activity can occur prior to the silver coating even becoming effective. Furthermore, the silver compound or silver element has an unpleasant color, from dark amber to black.
- compositions for providing antimicrobial capability to medical devices of various types, and particularly devices related to infusion therapy there is a need in the art for improved compositions for providing antimicrobial capability to medical devices of various types, and particularly devices related to infusion therapy.
- an effective antimicrobial coating that can be easily applied to medical devices constructed of polymeric materials and metals.
- improved methods of applying such antimicrobial coatings to medical devices are also a need for improved methods of applying such antimicrobial coatings to medical devices.
- the present invention has been developed in response to problems and needs in the art that have not yet been fully resolved by currently available antimicrobial compositions and methods.
- these compositions and methods are developed to reduce complications, such as the risk and occurrence of CRBSIs, by providing improved antimicrobial compositions and methods for use in conjunction with medical devices.
- the present invention relates to ultraviolet (UV) (wavelength of approximately 200 nm to 600 nm)-curable coatings that have antimicrobial properties.
- the coatings may be cured by light in the range set forth above, namely from about 200 nm to about 600 nm. In some embodiments, it may be preferable to cure the composition with light in the range of from about 300 nm to about 450 nm.
- These coatings are particularly adaptable for use on medical devices, particularly intravascular access devices like needleless valves.
- the medical devices are often comprised of polymeric substrates, especially polycarbonate (PC), polyurethane (PU), polyvinyl chloride (PVC), styrene-butadiene rubber (SBR), and acrylics.
- the surfaces of such devices are coated with a UV-curable coating (sometimes hereinafter referred to as “UV coating”) which comprises a UV curable composition and addition components incorporated therein such as antimicrobial agents uniformly distributed throughout its matrix.
- UV coating which comprises a UV curable composition and addition components incorporated therein such as antimicrobial agents uniformly distributed throughout its matrix.
- the antimicrobial agents are able to diffuse through the matrix and kill microscopic organisms that come in contact with the coating surface.
- the antimicrobial agents which are uniformly distributed in the UV coating matrix, gradually diffuse out of the matrix when the matrix is softened by IV fluids. The antimicrobial agents are then available to kill the microbes that come in contact with the coating surface.
- the formulations of this invention are generally comprised of a combination of urethane or polyester-type oligomer with acrylate-type functional groups, acrylate-type monomers, photoinitiators, rheological modifiers, and antimicrobial agents.
- the nano- or micro-sized particles of the antimicrobial agents are uniformly and permanently distributed throughout the whole coating matrix.
- the coatings are solventless and can be sprayed, wiped, dipped or distributed by using other conventional coating methods to coat a substrate's surface. They can then be rapidly cured with ultraviolet light. Curing may be completed in seconds or minutes depending on the formulation and curing conditions.
- the coatings of the present invention are generally efficacious within minutes instead of hours as with conventional coatings.
- the coatings also generally have a pleasant light color or an even clear color.
- oligomers can be used within the scope of the present invention. It is only necessary that the oligomer be capable of UV curing and of carrying antimicrobial agents of the type described herein.
- the oligomers can be acrylated aliphatic urethanes, acrylated aromatic urethanes, acrylated polyesters, unsaturated polyesters, acrylated polyethers, acrylated acrylics, and the like, or combinations of the above.
- the acrylated functional group can be mono-functional, di-functional, tri-functional, tetra-functional, penta-functional, or hexa-functional.
- the monomers can be 2-ethyl hexyl acrylate, isooctyl acrylate, isobornylacrylate, 1,6-hexanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, pentaerythritol tetra acrylate, penta erythritol tri acrylate, dimethoxy phenyl acetophenone hexyl methyl acrylate, 1,6 hexanidiol methacrylate, and the like, or combinations of these compounds.
- the composition should be provided with an adequate and compatible photoinitiator.
- the photoinitiators can be: 1) single molecule cleavage type, such as benzoin ethers, acetophenones, benzoyl oximes, and acyl phosphine oxide, and 2) hydrogen abstraction type, such as Michler's ketone, thioxanthone, anthroguionone, benzophenone, methyl diethanol amine, 2-N-butoxyethyl-4-(dimethylamino) benzoate, and the like, or combinations of these materials.
- a rheological modifier can preferrably be added to the composition.
- the rheological modifier allows the flow characteristics of the composition to be controlled and modified as desired.
- the rheological modifier can also aid in the uniform distribution of antimicrobial agent and other materials within the composition.
- Suitable rheological modifiers may include organic clay, castor wax, polyamide wax, polyurethane, and fumed silica or combinations of these materials.
- antimicrobial agents may be used in the compositions of the present invention. It is only necessary that the antimicrobial agent be compatible with the other components of the compositions and that it be effective in controlling microbial agents. Specifically, it is preferred that that antimicrobial agent not chemically react with the other components of the composition. As discussed above, in certain embodiments it is preferred that the antimicrobial agent be capable of moving within the matrix of the composition such that it can be delivered to the site of the microbial agent. Examples of suitable antimicrobial agents within the scope of the present invention include be aldehydes, anilides, biguanides, silver element or its compounds, bis-phenols, and quaternary ammonium compounds and the like or combinations of the above.
- the invention may be solventless.
- many conventional coatings employ harsh solvents such as THF and DMF.
- the present invention is operable without the use of solvents and, therefore, avoids the difficulties presented by the use of conventional solvents.
- the formulations demonstrate good adhesion to numerous plastic surfaces (such as PC, PU, PVC, acrylics, and SBR).
- the formulation can be cured with adequate ultraviolet light (wavelength of approximately 200 nm to 600 nm, and in certain embodiments in the range of from about 300 nm to about 450 nm).
- the present invention provides antimicrobial coating compositions which overcome many of the limitations of existing technology.
- the present invention employs known components which have achieved acceptance for medical use. These components are combined and used easily and efficiently.
- the compositions of the present invention generally including oligomers, monomers, photoinitiators, rheological modifiers, and suitable antimicrobial agents. The resulting compositions are easily applied to the surfaces of medical devices and quickly cured by UV light.
- an antimicrobial ultra violet (UV)-curable coating comprising a UV curable composition comprising an oligomer, a monomer, and a photoinitiator which are together capable of forming a UV curable polymer composition.
- the composition may also include a rheology modifier in order to improve the flow characteristics of the composition and uniform distribution of components within the compositions.
- an effective antimicrobial agent incorporated within the UV curable coating compositions is an effective antimicrobial agent.
- the UV curable coating compositions are comprised primarily of one or more oligomers and one or more monomers, combined with one or more suitable photoinitiators.
- the UV curable coating composition will comprise 100 parts by weight.
- Materials added to the UV curable coating composition may include rheological modifiers, antimicrobial agents, and other additives. These materials will be defined in parts by weight added to 100 parts by weight of the UV curable coating composition.
- the oligomer is generally selected from the group consisting of acrylated aliphatic urethanes, acrylated aromatic urethanes, acrylated polyesters, unsaturated polyesters, acrylated polyethers, acrylated acrylics, and the like, or combinations thereof.
- the acrylated functional group is selected from the group consisting of mono-functional, di-functional, tri-functional, tetra-functional, penta-functional, and hexa-functional acrylates. Any oligomer which is compatible with the other components of the composition is usable within the scope of the present invention.
- the oligomer will typically comprise from about 10% to about 90% of the UV curable composition. In some embodiments the oligomer will comprise from about 20% to about 80% of the UV curable composition. In certain embodiments of the invention the oligomer will comprise from about 30% to about 70% of the UV curable composition.
- the monomer is selected from the group consisting of 2-ethyl hexyl acrylate, isooctyl acrylate, isobornylacrylate, 1,6-hexanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, pentaerythritol tetra acrylate, penta erythritol tri acrylate, dimethoxy phenyl acetophenone hexyl methyl acrylate, 1,6 hexanidiol methacrylate and the like, or combinations of these compounds.
- any monomer which is compatible with the other components of the composition is usable within the scope of the present invention.
- the monomer will typically comprise from about 5% to about 90% of the UV curable composition. In some embodiments the monomer will comprise from about 10% to about 75% of the UV curable composition. In certain embodiments of the invention the monomer will comprise from about 20% to about 60% of the UV curable composition.
- the photoinitiator is selected from the group consisting of single molecule cleavage type, such as benzoin ethers, acetophenones, benzoyl oximes, and acyl phosphine oxide, and hydrogen abstraction types consisting of Michler's ketone, thioxanthone, anthroguionone, benzophenone, methyl diethanol amine, and 2-N-butoxyethyl-4-(dimethylamino) benzoate.
- the photoinitiaor will also be selected such that it is compatible with the other components of the composition is usable within the scope of the present invention.
- the photoinitiator will typically comprise from about 0.5% to about 10% of the UV curable composition. In some embodiments the photoinitiator will comprise from about 1% to about 8.5% of the UV curable composition. In certain embodiments of the invention the photoinitiator will comprise from about 2% to about 7% of the UV curable composition.
- UV curable composition As mentioned above, certain additional components are added to the UV curable composition. Prominent among these are suitable rheological modifiers and antimicrobial agents. As mentioned above, the amounts of these additional components will be expressed in parts by weight added to 100 parts by weight of UV-curable composition.
- the rheological modifier is selected from the group consisting of organic clay, castor wax, polyamide wax, polyurethane, and fumed silica.
- the Theological modifier generally comprises from about 0.1 to about 30 parts by weight added to 100 parts by weight of UV curable composition, i.e. the UV curable composition is 100 weight units, while the rheological modifier comprises from about 0.1 to about 30 parts of additional weight.
- the rheological modifier comprises from 0.1 to about 20 parts by weight compared to 100 parts by weight of the UV curable composition.
- the Theological modifier comprises from about 0.2 to about 10 parts by weight compared to 100 parts by weight of the UV curable composition.
- the antimicrobial agent is generally selected from the group consisting of aldehydes, anilides, biguanides, silver, silver compound, bis-phenols, and quaternary ammonium compounds.
- the antimicrobial agent is generally present in the amount of from about 0.5 to about 50 parts by weight in compared to 100 parts by weight of the UV curable composition. In other embodiments, the antimicrobial agent may be present in the amount of from about 0.5 to about 30 parts by weight of the composition. In certain further embodiments, the antimicrobial agent is present in the amount of from about 0.5 to about 20 parts by weight.
- the antimicrobial agent may either dissolve in the UV curable composition or may be uniformly distributed therein. In this manner it is found that sufficient antimicrobial agent can migrate within the composition to contact the location of microbial activity. In any event, it is preferred that the antimicrobial agent not react chemically with the other components of the compositions.
- the UV coating formulations can be urethane or polyester type arylate such as 7104, 7101, 7124-K, 7105-5K from Electronic Materials Inc. (EMI) (EM Breckenridge, Co.), 1168-M, I-20781 from Dymax Corporation (Torrington, Conn.), UV 630 from Permabond Engineering Adhesives (Somerset, N.J.).
- the viscosity of the coating should be less than 10,000 cps, preferable below 5,000 cps, and most preferably between 20 to 1,000 cps.
- UV-curable compositions within the scope of the present invention were formulated and their microbial kill rate and zone of inhibition were tested as set forth in Table 1 below. Each of the compositions was essentially identical except for the antimicrobial agent which was varied as set forth below.
- the composition was comprised of a UV curable composition designated EMI 7104.
- the UV curable composition was comprised of 30-70% oligomer, 20-60% monomer; 2-7% photoinitiator. Added to 100 parts of the UV curable composition was 2.6 parts fumed silica obtained from Cabot and designated Cabot's MS-55. Also added was 7.2 parts antimicrobial agent.
- the specific antimicrobial agent was used in the formulation were as follows:
- composition was tested on three (3) microbial agents, namely: Staphylococcus epidermidis (gram positive bacteria), Pseudomonas aeruginosa (gram negative bacteria), and Candida albicans (yeast or fungi). The results are summarized in Table 1.
- compositions were generally effective in killing the bacterial agents. All of the compositions, except that containing silver element, were effective in killing Candida albicans with one (1) hour. As set forth in Table 1 is appears that cetyl pyridium chloride and cetrimide were generally more effective than the other antimicrobial agents.
- UV curable coating compositions within the scope of the present invention.
- Each of the formulations included 100 parts of 7104 UV coating, 2.6 parts of fumed silica [designed M-5], and 5.0 parts of antimicrobial agent.
- Silver and chlorhexidine were included in the test because they are commonly used antimicrobial agents being used in medical technologies. The results of these tests are set forth in Table 2.
- formulation #1 cetyl pyridium chloride
- formulation #4 chlorhexidine diacetate
- both conventional compositions had 100% contact kill for selected microbes only after about 8 hours (both are using silver compound or silver element as the agent).
- Table 5 shows that the four agents identified above can have 100% contact kill within 1 hour and last up to almost 4 days when using S. epidermidis as the microbe. However, conventional silver agent formulations have no 1 hour contact kill at all starting from day 1.
- UV-curable composition was varied using various proprietary formulations manufactured by EMI.
- Antimicrobial activity was measured and compared to elongation at break. The data is as follows:
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CA2745191A CA2745191C (en) | 2008-12-01 | 2009-11-25 | Antimicrobial uv curable coating compositions |
PCT/US2009/065941 WO2010065421A1 (en) | 2008-12-01 | 2009-11-25 | Antimicrobial uv curable coating compositions |
ES09764419.9T ES2618803T3 (es) | 2008-12-01 | 2009-11-25 | Composiciones de recubrimiento curables por UV antimicrobianas sin disolvente |
AU2009322693A AU2009322693B2 (en) | 2008-12-01 | 2009-11-25 | Antimicrobial UV curable coating compositions |
JP2011539604A JP5615289B2 (ja) | 2008-12-01 | 2009-11-25 | 抗菌性uv硬化性コーティング組成物 |
CN2009801542921A CN102272245A (zh) | 2008-12-01 | 2009-11-25 | 抗微生物的uv可固化涂料组合物 |
KR1020117015127A KR101691679B1 (ko) | 2008-12-01 | 2009-11-25 | 항미생물성 자외선 경화성 코팅 조성물 |
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EP09764419.9A EP2370525B1 (en) | 2008-12-01 | 2009-11-25 | A solventless antimicrobial uv curable coating compositions |
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