WO1984001721A1 - Antimicrobial compositions - Google Patents

Antimicrobial compositions Download PDF

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Publication number
WO1984001721A1
WO1984001721A1 PCT/US1983/001404 US8301404W WO8401721A1 WO 1984001721 A1 WO1984001721 A1 WO 1984001721A1 US 8301404 W US8301404 W US 8301404W WO 8401721 A1 WO8401721 A1 WO 8401721A1
Authority
WO
WIPO (PCT)
Prior art keywords
percent
weight
antimicrobial
silver
acrylonitrile
Prior art date
Application number
PCT/US1983/001404
Other languages
French (fr)
Inventor
Dean G Laurin
James Stupar
Original Assignee
Baxter Travenol Lab
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 Baxter Travenol Lab filed Critical Baxter Travenol Lab
Priority to AU20398/83A priority Critical patent/AU2039883A/en
Publication of WO1984001721A1 publication Critical patent/WO1984001721A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/10—Metal compounds
    • C08K3/105—Compounds containing metals of Groups 1 to 3 or Groups 11 to 13 of the Periodic system
    • 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
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • 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
    • A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
    • A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
    • A61L2300/104—Silver, e.g. silver sulfadiazine

Definitions

  • compositions useful in making medical devices and useful in providing antimi- . crobial coatings on medical devices relate to compositions useful in making medical devices and useful in providing antimi- . crobial coatings on medical devices.
  • the invention particularly relates to antimicrobial compositions use ⁇ ful as coatings for medical connection devices and for making medical connection devices which are susceptible to touch contamination.
  • These compositions are also useful as antimicrobial coatings for access systems and lead devices (for example, shunts, cannulae, catheters, wires, enteral feeding tubes, endotracheal tubes, per ⁇ cutaneous devices and other solid or hollow tubular devices) used for a variety of medical purposes.
  • the compositions may be used as antimicrobial coatings for wound coverings or in the manufacture of thin, flexible, skin-like wound coverings.
  • Indwelling urethral catheterization is performed in approximately 10 to 15 percent of hospitalized patients. About 25 percent of these patients contract bacterial infections of the urinary tract.
  • compositions use ⁇ ful as coatings for urinary catheters, lead devices, medical connections susceptible to touch contamination and the like, and compositions useful as a material for making these various devices, whereby the proli ⁇ feration of bacteria thereon or in relatively close proximity thereto is inhibited. Inhibiting the proli ⁇ feration of bacteria on urinary catheters and catheter adapter connections would reduce the risk of urinary tract infections caused by bacteria accessing the urinary tract at these sites. It also would be de ⁇ sirable for the compositions to be easily applied as coatings on presently existing medical connections and devices. A desirable characteristic of such a composition would be an antimicrobial effect which is long lasting without being physiologically incompatible with nearby tissue.
  • antimicrobial compositions which find particular utility as coatings which inhibit the proliferation of bacteria near the surface of urinary catheters and the connec ⁇ tion between the catheter and the drainage tube, namely, the catheter/catheter adapter --unction site.
  • the anti ⁇ microbial coating on the catheter inhibits the prolifera ⁇ tion of bacteria in the area between the catheter and the walls of the urethra, and the antibacterial coating on the catheter adapter inhibits the proliferation of bacteria in the closed area connecting the catheter and the catheter adapter.
  • Catheters implanted in patients undergoing con- tinuous ambulatory peritoneal dialysis also can be coated with an antimicrobial composition of this in ⁇ vention.
  • An antimicrobial composition of this inven ⁇ tion can be applied as a coating to medical shunts, cannulae, catheters, wires and other solid or hollow tubular devices used for medical purposes.
  • the coating using an antimicrobial composition is prepared by mixing a suitable resin and a compound of a physiological , antimicrobial metal in an appropriate solvent for the resin.
  • the solvent should not adversely effect the activity of the metal compound as an antimicrobial agent.
  • the coating can be applied to a medical device by dipping in the mix ⁇ ture of resin, solvent, and physiological, antimicro ⁇ bial metal compound and thereafter allowing the solvent to evaporate. Both inside and outside surfaces may be coated.
  • the medical articles may be sprayed with the mixture and the solvent allowed to evaporate.
  • a volatile liquid carrier may be used with the resin dispersed in the volatile liquid. An article may be dipped or sprayed with this prepara ⁇ tion. Upon evaporation of the volatile liquid and curing of the resin a coating for the article is pro- vided.
  • articles can be made from a composition of a suitable resin and a compound of physiological, antimicrobial metal by molding the composition to form the article.
  • the resins used in formulating the mixture include, for example, acrylonitrile-butadiene-styrene copolymer, rigid polyvinyl chloride, curable silicones, alkoxy cured RTV silicone rubber, polyesters, rubber latexes (e.g., natural or synthetic polyisoprene), polyurethanes, styre ⁇ e-block copolymers (e.g., Kraton-D and Kraton-G, manufactured by Shell), ethylene copolymers (e.g., vinyl acetate, ethyl acrylate, or mixtures thereof), ethylene copolymers of maleic anhydride, acrylic acid or both, polycarbonates, nylons, and polymethyl methacrylate.
  • acrylonitrile-butadiene-styrene copolymer rigid polyvinyl chloride
  • physiological, antimicrobial metal compound Into a mixture of resin and solvent is added a quantity of physiological, antimicrobial metal compound.
  • a quantity of physiological, antimicro ⁇ bial metal compound may be mixed with a resin for direct molding of an article.
  • Physiological, antimicrobial metals are meant to include the precious metals, such as silver, gold and platinum, and copper and zinc.
  • Physiological, antimicrobial metal compounds used herein include oxides and salts of preferably silver and also gold, for example: silver acetate, silver benzoate, silver carbonate, silver citrate, silver chloride, sil ⁇ ver iodide, silver oxide, silver sulfate, gold chloride and gold oxide.
  • Platinum compounds such as chloropla- tinic acid or its salts (e.g., sodium and calcium chlo- roplatinate) may also be used.
  • compounds of copper and zinc may be used, for example: oxides and salts of copper and zinc such as those indicated above for silver.
  • Single physiological, antimicrobial metal compounds or combinations of physiological, antimicrobial metal compounds may be used.
  • Preferred physiological, antimicrobial metal compounds used in this invention are silver acetate, silver oxide, silver sulfate, gold chloride and a combination of silver oxide and gold chloride.
  • Pre- ferred quantities of physiological, antimicrobial metal compound are those sufficient to produce, within a 24 hour period, a solution of at least 10 ⁇ molar concentration of metal ion concentration in a stagnant film of liquid in contact with a surface of an article made from a composition of this invention or an article coated with a composition of this invention.
  • Figure 1 is an elevational view of a catheter adapter showing one end coated with an antimicrobial composition of this invention.
  • Figure 2 is an elevational view of a Foley catheter showing the portion of the catheter typically inserted into the urethra, coated with an antimicrobial compo ⁇ sition of this invention.
  • Figure 3 is a perspective view of the catheter adapter of this invention shown connecting a urinary drainage tube and a catheter.
  • FIG. 1 shows a conventional catheter adapter 10 after it has been coated with an antimicrobial composition of this in ⁇ vention.
  • Catheter adapter 10 has drainage tube end 12, catheter end 14, and injection site 16.
  • Catheter end 14 is spray coated or dip coated with an antimicrobial composition of this invention.
  • the shaded portion of catheter end 14 is illustrative of the coating.
  • FIG. 1 shows urinary catheter 18.
  • Catheter 18 has drainage connection 20 and inflation connection 22 for inflating the catheter balloon.
  • the shaded portion of catheter 18 illustrates the area coated by an antimicrobial composition of this invention. Typically, this coating will be applied to that portion of catheter 18 which resides in the urethra of a patient.
  • Catheter adapter 10 has the coated catheter end 14 connected to drainage connec ⁇ tion 20 of the catheter. Drainage tube end 12 is connected to drainage tube 24 to complete the connec ⁇ tion. Drainage tube 24 drains into a urinary drainage bag (not shown).
  • the risk of touch contamination of catheter end 14 is reduced by coating catheter end 14 of catheter adapter 10 with an antimicrobial composition of the present invention. Reducing the risk of touch contami ⁇ nation of catheter end 14 reduces the risk of subsequent urinary tract infection caused by a contaminated catheter adapter.
  • the antimicrobial composition coating catheter 18 inhibits the proliferation and migration of bacteria in a stagnant film between the coated catheter walls and the walls of the urethra. By inhibiting the pro ⁇ liferation and migration of bacteria through this route, subsequent urinary tract infection caused by such proliferation and migration of bacteria is re ⁇ quizd.
  • EXAMPLE 1 A mixture was made of 50 milliliters of methylene chloride, 5 grams of acrylonitrile-butadiene-styrene copolymer (LUSTRAN 240-29, a trademark of the Monsanto Company), and 1.2 grams of silver oxide powder. The mixture was stirred for approximately one hour.
  • a polyvinyl chloride catheter adapter used to connect a urinary catheter and drainage tubing for a urinary drainage connector, was coated on the exterior and the interior by dipping the connector into the mixture. Upon evaporation of the solvent, an antimicrobial coat ⁇ ing remained bonded to the catheter adapter. Catheter adapters can also be sprayed with the mixture.
  • EXAMPLE 2 A mixture was made by combining 50 milliliters of tetrahydrofuran, 5 grams of polyvinyl chloride (Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118), and 1.2 grams of silver oxide powder. The mixture was stirred for about one hour. Vinyl compatible catheter adapters may be either dip coated or spray coated with this mixture. By dip coating the catheter adapter, the exterior and interior surfaces may be conveniently coated. Upon evaporation of the solvent, tetrahydrofuran, an antimicrobial coat ⁇ ing will remain bonded to the device.
  • polyvinyl chloride Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118
  • EXAMPLE 3 Equivalent results may be obtained when a mixture is made by combining 25 milliliters of tetrahydrofuran, 25 milliliters of methylene chloride, 2.5 grams of acrylonitrile-butadiene-styrene copolymer (LUSTRAN 240-29), 2.5 grams of polyvinyl chloride (Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118), and 1.2 grams of silver oxide powder. The mixture may be stirred for about one hour.
  • a catheter adapter may be either dip coated or spray coated with this mixture. Upon evaporation of the solvents, an antimicrobial coating will remain bonded to the device.
  • EXAMPLE 4 A mixture was made by combining 10 milliliters of alkoxy curing RTV rubber, 65 milliliters of FREON TF solvent (FREON is a trademark of E. I. du pont de Nemours & Co.), and 5 grams of silver oxide powder. The mixture was stirred for about one hour.
  • FREON is a trademark of E. I. du pont de Nemours & Co.
  • a silicone rubber Foley catheter was dipped into this mixture and upon evaporation of the solvent and curing of the RTV, a flexible, antimicrobial coating on the interior and exterior surfaces of the silicone rubber catheter was provided. The coating adhered well to the catheter. Spray coating of the catheter is a viable alternative.
  • a mixture was made by combining 100 milliliters of tetrahydrofuran, 5 grams of acrylonitrile-butadiene- styrene copolymer (LUSTRAN 240-29) , and 1 gram of silver acetate. The mixture was stirred for about one hour. Acrylonitrile-butadiene-styrene compatible devices may be spray or dip coated with the mixture. Upon evapora ⁇ tion of the solvent, an antimicrobial coating will remain on the device.
  • EXAMPLE 6 Equivalent results may be obtained when a mixture is made by combining 100 milliliters of methylene chlo ⁇ ride, 5 grams of acrylonitrile-butadiene-styrene copoly ⁇ mer (LUSTRAN 240-29), and 1 gram of silver sulfate. The mixture may be stirred for about one hour. Acrylonitrile ⁇ butadiene-styrene compatible devices may be spray or dip coated with the mixture. Upon evaporation of the solvent, an antimicrobial coating will remain on the device.
  • EXAMPLE 8 Equivalent results may be obtained when a mixture is made by combining 25 milliliters of tetrahydrofuran, 25 milliliters of methylene chloride, 2.5 grams of acrylonitrile-butadiene-styrene copolymer (LUSTRAN 240-29), 2.5 grams of polyvinyl chloride (Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118), and 1.2 grams of gold chloride powder. The mixture may be stirred for about one hour. Devices may be either dip coated or spray coated with this mixture. Upon evaporation of • the solvents, an antimicrobial coating remains bonded to the device.
  • EXAMPLE 9 Equivalent results may be obtained when a mixture is made by combining 10 milliliters of alkoxy curing RTV, 65 milliliters of FREON TF solvent and 5 grams of gold chloride powder. The mixture may be stirred for about one hour.
  • a silicone rubber Foley catheter or other silicone rubber medical device may be dipped into this mixture and upon evaporation of the solvent and curing of the RTV, a flexible, antimicrobial coating for the silicone rubber catheter will be provided. Spray coating of the catheter is also a viable alternative.
  • Vinyl compatible catheter adapters or other medi ⁇ cal devices may be either dip coated or spray coated with this mixture. Upon evaporation of the solvent, tetrahydrofuran, an antimicrobial coating will remain on the device.
  • EXAMPLE 11 Equivalent results may be obtained when a mixture is made by combining 25 milliliters of tetrahydrofuran, 25 milliliters of methylene chloride, 2.5 grams of acrylonitrile-butadiene-stryrene copolymer (LUSTRAN).
  • EXAMPLE 12 Equivalent results may be obtained when a mixture is made by combining 10 milliliters of alkoxy curing RTV, 65 milliliters of FREON TF solvent, 5 grams of silver oxide powder, and 0.5 gram of gold chloride powder. The mixture may be stirred for about one hour. A silicone rubber Foley catheter or other silicone rubber medical device may be dipped into this mixture and upon evaporation of the solvent and curing of the RTV, a flexible, antimicrobial coating for the silicone rubber catheter is provided. Spray coating of the catheter is also an alternative application means.
  • Cured latex rubber devices may be dip coated with this mixture. Upon evaporation of the volatile liquid car ⁇ rier and curing of the coating mixture, an antimicrobial coating having high elastomeric characteristics will remain adhered to the device.

Abstract

Antimicrobial compositions finding particular utility for coating access systems, lead devices including shunts, cannulae, catheters (18), catheter adapters, wires and other solid or hollow tubular devices used for a variety of medical purposes. The composition comprises a material selected from the group consisting of acrylonitrilebutadiene-styrene copolymers, polyvinyl chloride, mixtures thereof, polyesters, polyurethanes, styreneblock copolymers, natural and synthetic rubbers, polycarbonates, nylon and silicone rubber mixed with an oligodynamic material consisting essentially of physiological, antimicrobial metals.

Description

ANTIMICROBIAL COMPOSITIONS
Field of the Invention
This invention relates to compositions useful in making medical devices and useful in providing antimi- . crobial coatings on medical devices. The invention particularly relates to antimicrobial compositions use¬ ful as coatings for medical connection devices and for making medical connection devices which are susceptible to touch contamination. These compositions are also useful as antimicrobial coatings for access systems and lead devices (for example, shunts, cannulae, catheters, wires, enteral feeding tubes, endotracheal tubes, per¬ cutaneous devices and other solid or hollow tubular devices) used for a variety of medical purposes. In addition, the compositions may be used as antimicrobial coatings for wound coverings or in the manufacture of thin, flexible, skin-like wound coverings.
Background of the Invention
Indwelling urethral catheterization is performed in approximately 10 to 15 percent of hospitalized patients. About 25 percent of these patients contract bacterial infections of the urinary tract. Two studies of note are. Garibaldi, R. A.; Burke, J. P.; Diσkman, M. L. ; and Smith, C. B., "Factors Predisposing to Bacteriuria During Indwelling Urethral Cathiterization". New Engl. J. Med., 291:215, 1974 and Kunin, C. M. and McCormack, R. C. , "Prevention of Catheter-Induced Urinary-Tract Infections by Sterile Closed Drainage". New Engl. J. Med., 274:1155, 1966. T e incidence of catheter-induced urinary tract infection still remains a problem despite various pro¬ phylactic measures that have been tried. Attempts to reduce the incidence of urinary tract infections have included the application of antibiotic ointments or other bactericidal agents to the surface of the cathe¬ ter, frequent bladder irrigation with concommittant prophylactic administration of antibiotics, or inhibi¬ tion of the growth of bacteria in urine drainage con¬ tainers. See, Akiyama, H. and Okamoto, S., "Prophylaxis of Indwelling Urethral Catheter Infection: Clinical Experience with a Modified Foley Catheter and Drainage System". The Journal of Urology, 121:40, 1979. United States Patent No. 4,054,139, Oligodynamic Catheter, to Crossley, teaches a catheter, or the like, which com¬ prises an oligodynamic agent such as metallic silver or its compounds, alone or in association with other heavy metals such as gold, for the purpose of reducing infection associated with these devices.
It would be desirable to provide compositions use¬ ful as coatings for urinary catheters, lead devices, medical connections susceptible to touch contamination and the like, and compositions useful as a material for making these various devices, whereby the proli¬ feration of bacteria thereon or in relatively close proximity thereto is inhibited. Inhibiting the proli¬ feration of bacteria on urinary catheters and catheter adapter connections would reduce the risk of urinary tract infections caused by bacteria accessing the urinary tract at these sites. It also would be de¬ sirable for the compositions to be easily applied as coatings on presently existing medical connections and devices. A desirable characteristic of such a composition would be an antimicrobial effect which is long lasting without being physiologically incompatible with nearby tissue.
OMPI
- . n?o Description of the Invention
In accordance with this invention, antimicrobial compositions are provided which find particular utility as coatings which inhibit the proliferation of bacteria near the surface of urinary catheters and the connec¬ tion between the catheter and the drainage tube, namely, the catheter/catheter adapter --unction site. The anti¬ microbial coating on the catheter inhibits the prolifera¬ tion of bacteria in the area between the catheter and the walls of the urethra, and the antibacterial coating on the catheter adapter inhibits the proliferation of bacteria in the closed area connecting the catheter and the catheter adapter.
Catheters implanted in patients undergoing con- tinuous ambulatory peritoneal dialysis also can be coated with an antimicrobial composition of this in¬ vention. An antimicrobial composition of this inven¬ tion can be applied as a coating to medical shunts, cannulae, catheters, wires and other solid or hollow tubular devices used for medical purposes.
Preferably, the coating using an antimicrobial composition is prepared by mixing a suitable resin and a compound of a physiological , antimicrobial metal in an appropriate solvent for the resin. The solvent should not adversely effect the activity of the metal compound as an antimicrobial agent. The coating can be applied to a medical device by dipping in the mix¬ ture of resin, solvent, and physiological, antimicro¬ bial metal compound and thereafter allowing the solvent to evaporate. Both inside and outside surfaces may be coated. Alternatively, the medical articles may be sprayed with the mixture and the solvent allowed to evaporate. Where appropriate, particularly with a latex rubber resin, a volatile liquid carrier may be used with the resin dispersed in the volatile liquid. An article may be dipped or sprayed with this prepara¬ tion. Upon evaporation of the volatile liquid and curing of the resin a coating for the article is pro- vided.
Indeed, articles can be made from a composition of a suitable resin and a compound of physiological, antimicrobial metal by molding the composition to form the article. The resins used in formulating the mixture include, for example, acrylonitrile-butadiene-styrene copolymer, rigid polyvinyl chloride, curable silicones, alkoxy cured RTV silicone rubber, polyesters, rubber latexes (e.g., natural or synthetic polyisoprene), polyurethanes, styreήe-block copolymers (e.g., Kraton-D and Kraton-G, manufactured by Shell), ethylene copolymers (e.g., vinyl acetate, ethyl acrylate, or mixtures thereof), ethylene copolymers of maleic anhydride, acrylic acid or both, polycarbonates, nylons, and polymethyl methacrylate. Into a mixture of resin and solvent is added a quantity of physiological, antimicrobial metal compound. Alternatively, a quantity of physiological, antimicro¬ bial metal compound may be mixed with a resin for direct molding of an article. Physiological, antimicrobial metals are meant to include the precious metals, such as silver, gold and platinum, and copper and zinc. Physiological, antimicrobial metal compounds used herein include oxides and salts of preferably silver and also gold, for example: silver acetate, silver benzoate, silver carbonate, silver citrate, silver chloride, sil¬ ver iodide, silver oxide, silver sulfate, gold chloride and gold oxide. Platinum compounds such as chloropla- tinic acid or its salts (e.g., sodium and calcium chlo- roplatinate) may also be used. Also, compounds of copper and zinc may be used, for example: oxides and salts of copper and zinc such as those indicated above for silver. Single physiological, antimicrobial metal compounds or combinations of physiological, antimicrobial metal compounds may be used.
Preferred physiological, antimicrobial metal compounds used in this invention are silver acetate, silver oxide, silver sulfate, gold chloride and a combination of silver oxide and gold chloride. Pre- ferred quantities of physiological, antimicrobial metal compound are those sufficient to produce, within a 24 hour period, a solution of at least 10~ molar concentration of metal ion concentration in a stagnant film of liquid in contact with a surface of an article made from a composition of this invention or an article coated with a composition of this invention.
Brief Description of the Drawings
For a more complete understanding of this inven¬ tion, reference should now be had to the embodiments illustrated in greater detail in the accompanying drawings.
In the drawings:
Figure 1 is an elevational view of a catheter adapter showing one end coated with an antimicrobial composition of this invention. Figure 2 is an elevational view of a Foley catheter showing the portion of the catheter typically inserted into the urethra, coated with an antimicrobial compo¬ sition of this invention.
Figure 3 is a perspective view of the catheter adapter of this invention shown connecting a urinary drainage tube and a catheter.
Detailed Description of the Drawings
Turning now to the drawings. Figure 1 shows a conventional catheter adapter 10 after it has been coated with an antimicrobial composition of this in¬ vention. Catheter adapter 10 has drainage tube end 12, catheter end 14, and injection site 16.
Catheter end 14 is spray coated or dip coated with an antimicrobial composition of this invention. The shaded portion of catheter end 14 is illustrative of the coating.
Figure 2 shows urinary catheter 18. Catheter 18 has drainage connection 20 and inflation connection 22 for inflating the catheter balloon.
The shaded portion of catheter 18 illustrates the area coated by an antimicrobial composition of this invention. Typically, this coating will be applied to that portion of catheter 18 which resides in the urethra of a patient.
A typical connection of catheter adapter 10 is illustrated in Figure 3. Catheter adapter 10 has the coated catheter end 14 connected to drainage connec¬ tion 20 of the catheter. Drainage tube end 12 is connected to drainage tube 24 to complete the connec¬ tion. Drainage tube 24 drains into a urinary drainage bag (not shown).
The risk of touch contamination of catheter end 14 is reduced by coating catheter end 14 of catheter adapter 10 with an antimicrobial composition of the present invention. Reducing the risk of touch contami¬ nation of catheter end 14 reduces the risk of subsequent urinary tract infection caused by a contaminated catheter adapter.
The antimicrobial composition coating catheter 18 inhibits the proliferation and migration of bacteria in a stagnant film between the coated catheter walls and the walls of the urethra. By inhibiting the pro¬ liferation and migration of bacteria through this route, subsequent urinary tract infection caused by such proliferation and migration of bacteria is re¬ duced.
The examples below are offered for illustrative purposes only and are not intended to limit the scope of the invention of this application, which is as de- fined in the claims below.
EXAMPLE 1 A mixture was made of 50 milliliters of methylene chloride, 5 grams of acrylonitrile-butadiene-styrene copolymer (LUSTRAN 240-29, a trademark of the Monsanto Company), and 1.2 grams of silver oxide powder. The mixture was stirred for approximately one hour. A polyvinyl chloride catheter adapter, used to connect a urinary catheter and drainage tubing for a urinary drainage connector, was coated on the exterior and the interior by dipping the connector into the mixture. Upon evaporation of the solvent, an antimicrobial coat¬ ing remained bonded to the catheter adapter. Catheter adapters can also be sprayed with the mixture.
EXAMPLE 2 A mixture was made by combining 50 milliliters of tetrahydrofuran, 5 grams of polyvinyl chloride (Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118), and 1.2 grams of silver oxide powder. The mixture was stirred for about one hour. Vinyl compatible catheter adapters may be either dip coated or spray coated with this mixture. By dip coating the catheter adapter, the exterior and interior surfaces may be conveniently coated. Upon evaporation of the solvent, tetrahydrofuran, an antimicrobial coat¬ ing will remain bonded to the device.
EXAMPLE 3 Equivalent results may be obtained when a mixture is made by combining 25 milliliters of tetrahydrofuran, 25 milliliters of methylene chloride, 2.5 grams of acrylonitrile-butadiene-styrene copolymer (LUSTRAN 240-29), 2.5 grams of polyvinyl chloride (Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118), and 1.2 grams of silver oxide powder. The mixture may be stirred for about one hour.
A catheter adapter may be either dip coated or spray coated with this mixture. Upon evaporation of the solvents, an antimicrobial coating will remain bonded to the device.
EXAMPLE 4 A mixture was made by combining 10 milliliters of alkoxy curing RTV rubber, 65 milliliters of FREON TF solvent (FREON is a trademark of E. I. du pont de Nemours & Co.), and 5 grams of silver oxide powder. The mixture was stirred for about one hour.
A silicone rubber Foley catheter was dipped into this mixture and upon evaporation of the solvent and curing of the RTV, a flexible, antimicrobial coating on the interior and exterior surfaces of the silicone rubber catheter was provided. The coating adhered well to the catheter. Spray coating of the catheter is a viable alternative.
EXAMPLE 5
A mixture was made by combining 100 milliliters of tetrahydrofuran, 5 grams of acrylonitrile-butadiene- styrene copolymer (LUSTRAN 240-29) , and 1 gram of silver acetate. The mixture was stirred for about one hour. Acrylonitrile-butadiene-styrene compatible devices may be spray or dip coated with the mixture. Upon evapora¬ tion of the solvent, an antimicrobial coating will remain on the device.
EXAMPLE 6 Equivalent results may be obtained when a mixture is made by combining 100 milliliters of methylene chlo¬ ride, 5 grams of acrylonitrile-butadiene-styrene copoly¬ mer (LUSTRAN 240-29), and 1 gram of silver sulfate. The mixture may be stirred for about one hour. Acrylonitrile¬ butadiene-styrene compatible devices may be spray or dip coated with the mixture. Upon evaporation of the solvent, an antimicrobial coating will remain on the device.
EXAMPLE 7 Equivalent results may be obtained when a mixture is made by combining 50 milliliters of tetrahydrofuran, 5 grams of polyvinyl chloride (Alpha Plastics and
Chemicals, clear rigid vinyl 2212/7-118), and 1.2 grams of gold chloride powder. The mixture may be stirred for about one hour. Polyvinyl chloride compatible de¬ vices may be spray or dip coated with the mixture. Upon evaporation of the solvent, an antimicrobial coating will remain on the device.
EXAMPLE 8 Equivalent results may be obtained when a mixture is made by combining 25 milliliters of tetrahydrofuran, 25 milliliters of methylene chloride, 2.5 grams of acrylonitrile-butadiene-styrene copolymer (LUSTRAN 240-29), 2.5 grams of polyvinyl chloride (Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118), and 1.2 grams of gold chloride powder. The mixture may be stirred for about one hour. Devices may be either dip coated or spray coated with this mixture. Upon evaporation of • the solvents, an antimicrobial coating remains bonded to the device.
EXAMPLE 9 Equivalent results may be obtained when a mixture is made by combining 10 milliliters of alkoxy curing RTV, 65 milliliters of FREON TF solvent and 5 grams of gold chloride powder. The mixture may be stirred for about one hour.
A silicone rubber Foley catheter or other silicone rubber medical device may be dipped into this mixture and upon evaporation of the solvent and curing of the RTV, a flexible, antimicrobial coating for the silicone rubber catheter will be provided. Spray coating of the catheter is also a viable alternative.
EXAMPLE 10
Equivalent results may be obtained when a mixture is made by combining 50 milliliters of tetrahydrofuran, 5 grams of polyvinyl chloride (Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118), 1.2 grams of silver oxide powder, and 0.1 gram of gold chloride powder. The mixture may be stirred for about one hour.
Vinyl compatible catheter adapters or other medi¬ cal devices may be either dip coated or spray coated with this mixture. Upon evaporation of the solvent, tetrahydrofuran, an antimicrobial coating will remain on the device.
" EXAMPLE 11 Equivalent results may be obtained when a mixture is made by combining 25 milliliters of tetrahydrofuran, 25 milliliters of methylene chloride, 2.5 grams of acrylonitrile-butadiene-stryrene copolymer (LUSTRAN
240-29), 2.5 grams of polyvinyl chloride (Alpha Plastics and Chemicals, clear rigid vinyl 2212/7-118), 1.2 grams of silver oxide powder, and 0.1 gram of gold chloride powder. The mixture may be stirred for about one hour. Devices may be either dip coated or spray coated with this mixture. Upon evaporation of the solvents, an antimicrobial coating will remain on the device.
EXAMPLE 12 Equivalent results may be obtained when a mixture is made by combining 10 milliliters of alkoxy curing RTV, 65 milliliters of FREON TF solvent, 5 grams of silver oxide powder, and 0.5 gram of gold chloride powder. The mixture may be stirred for about one hour. A silicone rubber Foley catheter or other silicone rubber medical device may be dipped into this mixture and upon evaporation of the solvent and curing of the RTV, a flexible, antimicrobial coating for the silicone rubber catheter is provided. Spray coating of the catheter is also an alternative application means.
EXAMPLE 13
Equivalent results may be obtained when a mixture is made by combining 100 milliliters of natural rubber latex with 10 grams of silver oxide powder. The mixture may be stirred until the silver oxide is dispersed.
Cured latex rubber devices may be dip coated with this mixture. Upon evaporation of the volatile liquid car¬ rier and curing of the coating mixture, an antimicrobial coating having high elastomeric characteristics will remain adhered to the device.
EXAMPLE 14
Equivalent results may be obtained when a mixture is made by combining 50 milliliters of methylene chlo¬ ride, 5 grams of acrylonitrile-butadiene-styrene copoly¬ mer (LUSTRAN 240-29), and 1.2 grams of copper oxide powder. The mixture may be stirred for about one hour. A catheter adapter may be either dip coated or spray coated with this mixture. Upon evaporation of the solvent, an antimicrobial coating will remain bonded to the device.
EXAMPLE 15
Equivalent results may be obtained when a mixture is made by combining 50 milliliters of methylene chlo¬ ride, 5 grams of acrylonitrile-butadiene-styrene copoly¬ mer (LUSTRAN 240-29), and 1.2 grams of zinc oxide powder. The mixture may be stirred for about one hour. A cathe¬ ter adapter may be either dip coated or spray coated with this mixture. Upon evaporation of the solvent, an antimicrobial coating will remain bonded to the de¬ vice.
O PI

Claims

1. An antimicrobial composition comprising:
30 to 85 percent by weight of a binder consisting essentially of a material selected from the group con¬ sisting of acrylonitrile-butadiene-styrene copolymers, polyvinyl chloride, mixtures thereof, polyesters, poly- urethanes, styrene-block copolymers, natural and syn¬ thetic rubbers, polycarbonates, nylon and silicone rubber; and,
15 to 70 percent by weight of an antimicrobial agent selected from the group consisting of compounds of physiological, antimicrobial metals and mixtures thereof.
2. The antimicrobial composition of Claim 1 in which said mixtures of acrylonitrile-butadiene-styrene copolymers and polyvinyl chloride consist of 25 to 75 percent by weight of acrylonitrile-butadiene-styrene copolymers and 25 to 75 percent by weight of polyvinyl chloride.
3. The antimicrobial composition of Claim 1 in which said antimicrobial agent is selected from the group consisting of oxides and salts of silver and gold.
4. The antimicrobial composition of Claim 1 in which said antimicrobial agent is selected from the group consisting of silver compounds.
5. The antimicrobial composition of Claim 4 in which said antimicrobial agent is silver oxide.
6. An antimicrobial composition for coating articles comprising:
30 to 85 percent by weight of a binder consisting essentially of acrylonitrile-butadiene-styrene copoly¬ mers; and,
15 to 70 percent by weight of an antimicrobial agent selected from the group consisting essentially of silver compounds and mixtures thereof whereby the particles of silver compound are exposed on the coating layer on the surface of the article and being sufficiently mobile to produce, within 24 hours, a solution of at least 10 —6 molar concentration of silver ion concentration in a stagnant film of urine in contact with said surface.
7. An antimicrobial composition for coating articles comprising:
30 to 85 percent by weight of a binder consisting essentially of a mixture consisting of 35 to 65 percent by weight of acrylonitrile-butadiene-styrene copolymers and 35 to 65 percent by weight of polyvinyl chloride; and,
15 to 70 percent by weight of an antimicrobial agent consisting essentially of silver oxide whereby the particles of silver oxide are exposed on the coating layer on the outermost surface of the article and being sufficiently mobile to produce, within 24 hours, a solution of at least 10" molar concentration of silver ion concentration in a stagnant film of urine in contact with said surface.
8. The antimicrobial composition of Claim 7 in which said mixtures of acrylonitrile-butadiene-styrene copolymers and polyvinyl chloride consist of 50 percent by weight of acrylonitrile-butadiene-styrene copolymers and 50 percent by weight of polyvinyl chloride.
YΛ/ , IPO
PCT/US1983/001404 1982-11-05 1983-09-15 Antimicrobial compositions WO1984001721A1 (en)

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EP0138851A1 (en) * 1983-04-18 1985-05-02 BAXTER INTERNATIONAL INC. (a Delaware corporation) Articles and compositions providing antimicrobial effect during urinary drainage
EP0190504A2 (en) * 1984-12-28 1986-08-13 Johnson Matthey Public Limited Company Antimicrobial compositions
EP0197068A1 (en) * 1984-10-01 1986-10-15 BAXTER INTERNATIONAL INC. (a Delaware corporation) Antimicrobial compositions
US4810247A (en) * 1985-11-21 1989-03-07 Glassman Jacob A Urinary catheter and penile-cup
DE3729253A1 (en) * 1987-09-02 1989-03-23 Ulrich Dr Mueller Device for preventing infections in external fixators in bone surgery
EP0579995A1 (en) * 1992-07-04 1994-01-26 STERIMED Medizinprodukte GmbH Catheterset
DE4403016A1 (en) * 1994-02-01 1995-08-03 Krall Theodor Dipl Ing Microbicidal plastic articles partic. for medical use
DE19607314A1 (en) * 1996-02-27 1997-08-28 Orthomed Chirurgische Instr Gm Body exhibiting antibacterial activity for use as a medical or surgical aid
US5848995A (en) * 1993-04-09 1998-12-15 Walder; Anthony J. Anti-infective medical article and method for its preparation
WO2000015288A1 (en) * 1998-09-17 2000-03-23 Kdf Fluid Treatment, Inc. Antimicrobial urinary catheter
EP0956838A3 (en) * 1998-05-11 2000-06-07 Medistar S.r.l. Body-fluid collecting device
US6191192B1 (en) 1997-06-23 2001-02-20 Toyo Boseki Kabushiki Kaisha Antibacterial polymeric moldings
WO2002015954A1 (en) * 2000-08-18 2002-02-28 Medtronic Minimed, Inc. Subcutaneous infusion cannula
WO2002017984A1 (en) * 2000-08-31 2002-03-07 Bio-Gate Bioinnovative Materials Gmbh Antimicrobial material for implanting in bones
WO2002043743A1 (en) * 2000-11-29 2002-06-06 Bristol-Myers Squibb Company Light stabilized antimicrobial materials
WO2004000380A1 (en) * 2002-06-19 2003-12-31 Scimed Life Systems, Inc. Implatable or insertable medical devices for controlled delivery of a therapeutic agent
WO2004000381A1 (en) * 2002-06-19 2003-12-31 Scimed Life Systems, Inc. Implantable or insertable medical devices for controlled delivery of a therapeutic agent
US6716895B1 (en) 1999-12-15 2004-04-06 C.R. Bard, Inc. Polymer compositions containing colloids of silver salts
US6897349B2 (en) 1997-11-14 2005-05-24 Acrymed Silver-containing compositions, devices and methods for making
WO2005056102A1 (en) * 2003-12-15 2005-06-23 Nitricare Kb Device and method for administering therapeutic agents
WO2006113052A3 (en) * 2005-04-14 2006-12-07 3M Innovative Properties Co Silver coatings and methods of manufacture
CN101160146A (en) * 2005-04-14 2008-04-09 3M创新有限公司 Silver coatings and methods of manufacture
US7476698B2 (en) 2001-09-18 2009-01-13 Bio-Gate Ag Antimicrobial adhesive and coating substance and method for the production thereof
US8034454B2 (en) * 1999-12-15 2011-10-11 C.R. Bard, Inc. Antimicrobial compositions containing colloids of oligodynamic metals
US8193267B2 (en) 2003-12-05 2012-06-05 3M Innovative Properties Company Polymer compositions with bioactive agent, medical articles, and methods
US8821912B2 (en) 2009-12-11 2014-09-02 Difusion Technologies, Inc. Method of manufacturing antimicrobial implants of polyetheretherketone
US8900624B2 (en) 2004-07-30 2014-12-02 Kimberly-Clark Worldwide, Inc. Antimicrobial silver compositions
WO2014209095A1 (en) 2013-06-25 2014-12-31 Servicios Administrates Penoles, S.A. De C.V. Bacteriostatic and fungistatic additive in masterbatch for application in plastics, and method for producing same
US9107765B2 (en) 2010-05-07 2015-08-18 Difusion Technologies, Inc. Medical implants with increased hydrophilicity
US9289450B2 (en) 2006-01-13 2016-03-22 3M Innovative Properties Company Silver-containing antimicrobial articles and methods of manufacture
US9492584B2 (en) 2009-11-25 2016-11-15 Difusion Technologies, Inc. Post-charging of zeolite doped plastics with antimicrobial metal ions
US9687503B2 (en) 1999-12-30 2017-06-27 Avent, Inc. Devices for delivering oxygen to the wounds
US20170231821A1 (en) * 2016-01-19 2017-08-17 Kci Usa, Inc. Silicone wound contact layer with silver
WO2017157416A1 (en) 2016-03-14 2017-09-21 Observe Medical Aps Biofilm prevention in catheter systems
US10251392B2 (en) 2004-07-30 2019-04-09 Avent, Inc. Antimicrobial devices and compositions
US10493101B2 (en) 2005-12-14 2019-12-03 Convatec Technologies Inc. Antimicrobial composition
US11135315B2 (en) 2010-11-30 2021-10-05 Convatec Technologies Inc. Composition for detecting biofilms on viable tissues
US11286601B2 (en) 2012-12-20 2022-03-29 Convatec Technologies, Inc. Processing of chemically modified cellulosic fibres

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Cited By (56)

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Publication number Priority date Publication date Assignee Title
EP0138851A1 (en) * 1983-04-18 1985-05-02 BAXTER INTERNATIONAL INC. (a Delaware corporation) Articles and compositions providing antimicrobial effect during urinary drainage
EP0138851A4 (en) * 1983-04-18 1986-11-26 Baxter Travenol Lab Articles and compositions providing antimicrobial effect during urinary drainage.
EP0197068A1 (en) * 1984-10-01 1986-10-15 BAXTER INTERNATIONAL INC. (a Delaware corporation) Antimicrobial compositions
EP0197068A4 (en) * 1984-10-01 1988-05-31 Baxter Travenol Lab Antimicrobial compositions.
EP0190504A2 (en) * 1984-12-28 1986-08-13 Johnson Matthey Public Limited Company Antimicrobial compositions
EP0190504A3 (en) * 1984-12-28 1987-05-20 Johnson Matthey Public Limited Company Antimicrobial compositions
US4810247A (en) * 1985-11-21 1989-03-07 Glassman Jacob A Urinary catheter and penile-cup
DE3729253A1 (en) * 1987-09-02 1989-03-23 Ulrich Dr Mueller Device for preventing infections in external fixators in bone surgery
EP0579995A1 (en) * 1992-07-04 1994-01-26 STERIMED Medizinprodukte GmbH Catheterset
US5848995A (en) * 1993-04-09 1998-12-15 Walder; Anthony J. Anti-infective medical article and method for its preparation
DE4403016A1 (en) * 1994-02-01 1995-08-03 Krall Theodor Dipl Ing Microbicidal plastic articles partic. for medical use
DE19607314A1 (en) * 1996-02-27 1997-08-28 Orthomed Chirurgische Instr Gm Body exhibiting antibacterial activity for use as a medical or surgical aid
US6191192B1 (en) 1997-06-23 2001-02-20 Toyo Boseki Kabushiki Kaisha Antibacterial polymeric moldings
US7576255B2 (en) 1997-11-14 2009-08-18 Acrymed, Inc. Silver-containing compositions, devices, and methods for making
US6897349B2 (en) 1997-11-14 2005-05-24 Acrymed Silver-containing compositions, devices and methods for making
EP0956838A3 (en) * 1998-05-11 2000-06-07 Medistar S.r.l. Body-fluid collecting device
WO2000015288A1 (en) * 1998-09-17 2000-03-23 Kdf Fluid Treatment, Inc. Antimicrobial urinary catheter
US6716895B1 (en) 1999-12-15 2004-04-06 C.R. Bard, Inc. Polymer compositions containing colloids of silver salts
US8034454B2 (en) * 1999-12-15 2011-10-11 C.R. Bard, Inc. Antimicrobial compositions containing colloids of oligodynamic metals
US9687503B2 (en) 1999-12-30 2017-06-27 Avent, Inc. Devices for delivering oxygen to the wounds
WO2002015954A1 (en) * 2000-08-18 2002-02-28 Medtronic Minimed, Inc. Subcutaneous infusion cannula
EP1621217A2 (en) 2000-08-31 2006-02-01 Bio-Gate Bioinnovative Materials GmbH Antimicrobial powder and material
US6984392B2 (en) 2000-08-31 2006-01-10 Bio-Gate Bioinnovative Materials Gmbh Antimicrobial material for implanting in bones
WO2002017984A1 (en) * 2000-08-31 2002-03-07 Bio-Gate Bioinnovative Materials Gmbh Antimicrobial material for implanting in bones
EP1621217A3 (en) * 2000-08-31 2006-06-28 Bio-Gate Bioinnovative Materials GmbH Antimicrobial powder and material
US6669981B2 (en) 2000-11-29 2003-12-30 Bristol-Myers Squibb Company Light stabilized antimicrobial materials
WO2002043743A1 (en) * 2000-11-29 2002-06-06 Bristol-Myers Squibb Company Light stabilized antimicrobial materials
KR100770077B1 (en) 2000-11-29 2007-10-24 브리스톨-마이어스 스퀴브 캄파니 Light Stabilized Antimicrobial Materials
US7267828B2 (en) 2000-11-29 2007-09-11 Bristol-Myers Squibb Company Light stabilized antimicrobial materials
US7476698B2 (en) 2001-09-18 2009-01-13 Bio-Gate Ag Antimicrobial adhesive and coating substance and method for the production thereof
US7105175B2 (en) 2002-06-19 2006-09-12 Boston Scientific Scimed, Inc. Implantable or insertable medical devices for controlled delivery of a therapeutic agent
US7901702B2 (en) 2002-06-19 2011-03-08 Boston Scientific Scimed, Inc. Implantable or insertable medical devices for controlled delivery of a therapeutic agent
WO2004000381A1 (en) * 2002-06-19 2003-12-31 Scimed Life Systems, Inc. Implantable or insertable medical devices for controlled delivery of a therapeutic agent
WO2004000380A1 (en) * 2002-06-19 2003-12-31 Scimed Life Systems, Inc. Implatable or insertable medical devices for controlled delivery of a therapeutic agent
US8193267B2 (en) 2003-12-05 2012-06-05 3M Innovative Properties Company Polymer compositions with bioactive agent, medical articles, and methods
WO2005056102A1 (en) * 2003-12-15 2005-06-23 Nitricare Kb Device and method for administering therapeutic agents
US10251392B2 (en) 2004-07-30 2019-04-09 Avent, Inc. Antimicrobial devices and compositions
US8900624B2 (en) 2004-07-30 2014-12-02 Kimberly-Clark Worldwide, Inc. Antimicrobial silver compositions
US9888691B2 (en) 2004-07-30 2018-02-13 Avent, Inc. Antimicrobial silver compositions
CN101160146A (en) * 2005-04-14 2008-04-09 3M创新有限公司 Silver coatings and methods of manufacture
WO2006113052A3 (en) * 2005-04-14 2006-12-07 3M Innovative Properties Co Silver coatings and methods of manufacture
US10493101B2 (en) 2005-12-14 2019-12-03 Convatec Technologies Inc. Antimicrobial composition
US9289450B2 (en) 2006-01-13 2016-03-22 3M Innovative Properties Company Silver-containing antimicrobial articles and methods of manufacture
US9492584B2 (en) 2009-11-25 2016-11-15 Difusion Technologies, Inc. Post-charging of zeolite doped plastics with antimicrobial metal ions
US8821912B2 (en) 2009-12-11 2014-09-02 Difusion Technologies, Inc. Method of manufacturing antimicrobial implants of polyetheretherketone
US9132576B2 (en) 2009-12-11 2015-09-15 Difusion Technologies, Inc. Method of manufacturing antimicrobial implants of polyetheretherketone
US8840914B2 (en) 2009-12-11 2014-09-23 Difusion Technologies, Inc. Method of manufacturing antimicrobial implants of polyetheretherketone
US9375321B2 (en) 2010-05-07 2016-06-28 Difusion Technologies, Inc. Medical implants with increased hydrophilicity
US9107765B2 (en) 2010-05-07 2015-08-18 Difusion Technologies, Inc. Medical implants with increased hydrophilicity
US11135315B2 (en) 2010-11-30 2021-10-05 Convatec Technologies Inc. Composition for detecting biofilms on viable tissues
US11286601B2 (en) 2012-12-20 2022-03-29 Convatec Technologies, Inc. Processing of chemically modified cellulosic fibres
WO2014209095A1 (en) 2013-06-25 2014-12-31 Servicios Administrates Penoles, S.A. De C.V. Bacteriostatic and fungistatic additive in masterbatch for application in plastics, and method for producing same
EP3575263A1 (en) 2013-06-25 2019-12-04 Servicios Administrativos Peñoles S.A. de C.V Bacteriostatic and fungistatic additive in masterbatch for application in plastics, and method for producing same
US20170231821A1 (en) * 2016-01-19 2017-08-17 Kci Usa, Inc. Silicone wound contact layer with silver
WO2017157416A1 (en) 2016-03-14 2017-09-21 Observe Medical Aps Biofilm prevention in catheter systems
US11213651B2 (en) 2016-03-14 2022-01-04 Observe Medical Aps Biofilm prevention in catheter systems

Also Published As

Publication number Publication date
EP0124536A1 (en) 1984-11-14
ES527051A0 (en) 1985-05-01
EP0124536A4 (en) 1985-06-06
ES8504464A1 (en) 1985-05-01
CA1224717A (en) 1987-07-28

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