WO2014003858A1 - Nonwoven materials containing chlorhexidine acetate and triclosan - Google Patents
Nonwoven materials containing chlorhexidine acetate and triclosan Download PDFInfo
- Publication number
- WO2014003858A1 WO2014003858A1 PCT/US2013/032506 US2013032506W WO2014003858A1 WO 2014003858 A1 WO2014003858 A1 WO 2014003858A1 US 2013032506 W US2013032506 W US 2013032506W WO 2014003858 A1 WO2014003858 A1 WO 2014003858A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- triclosan
- chlorhexidine acetate
- coating
- formulation
- articles
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 63
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229960003500 triclosan Drugs 0.000 title claims abstract description 50
- 229960002152 chlorhexidine acetate Drugs 0.000 title claims abstract description 40
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000576 coating method Methods 0.000 claims abstract description 21
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- -1 polypropylene Polymers 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 230000000845 anti-microbial effect Effects 0.000 abstract description 24
- 230000004888 barrier function Effects 0.000 abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 27
- 238000009472 formulation Methods 0.000 description 25
- 230000002706 hydrostatic effect Effects 0.000 description 12
- 230000009467 reduction Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000004744 fabric Substances 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 description 9
- 229920002413 Polyhexanide Polymers 0.000 description 9
- 239000004599 antimicrobial Substances 0.000 description 9
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 8
- 229960003333 chlorhexidine gluconate Drugs 0.000 description 8
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 229960003260 chlorhexidine Drugs 0.000 description 7
- 239000012458 free base Substances 0.000 description 5
- 239000004745 nonwoven fabric Substances 0.000 description 5
- 206010041925 Staphylococcal infections Diseases 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000012669 liquid formulation Substances 0.000 description 4
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 206010029803 Nosocomial infection Diseases 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 206010011409 Cross infection Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical compound CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 description 1
- 229950010221 alexidine Drugs 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WDRFFJWBUDTUCA-UHFFFAOYSA-N chlorhexidine acetate Chemical compound CC(O)=O.CC(O)=O.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WDRFFJWBUDTUCA-UHFFFAOYSA-N 0.000 description 1
- 229960001884 chlorhexidine diacetate Drugs 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 229940085942 formulation r Drugs 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B46/00—Surgical drapes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B46/00—Surgical drapes
- A61B46/40—Drape material, e.g. laminates; Manufacture thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/048—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/146—Porous materials, e.g. foams or sponges
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- 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
-
- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2321/00—Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D10B2321/02—Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds polyolefins
- D10B2321/022—Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds polyolefins polypropylene
-
- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2509/00—Medical; Hygiene
Definitions
- the present invention is directed to medical articles having antimicrobial efficacy and good barrier properties.
- the key test for measuring the barrier performance of a material is the Water Resistance: Hydrostatic Pressure Test, AATCC Test Method 127, which was established by the American Association of Textile Chemists and Colorists.
- the hydrostatic pressure test measures the resistance of a material to the penetration of water under increasing pressure.
- Materials having an AAMI Level 1 classification pass a spray impact test and are effective for impact penetration. Examples of materials typically having an AAMI Level 1 classification include basic cover gowns and isolation gowns.
- Materials having an AAMI Level 2 classification require a hydrostatic pressure of at least 20 cmH 2 0 for water to penetrate through the material.
- Examples of materials typically having an AAMI Level 2 classification include articles that offer basic protection and are often used when the amount of exposure to fluids is relatively small and for a short period of time.
- Materials having an AAMI Level 3 classification require a hydrostatic pressure of at least 50 cmH 2 0 for water to penetrate through the material.
- Examples of materials typically having an AAMI Level 3 classification include articles that offer increased barrier protection and are often used when the amount of fluid exposure is moderate.
- Materials having an AAMI Level 4 classification are impervious to water passing through. Surgical drapes and gowns often have an AAMI Level 4 classification.
- Some nonwoven materials are coated with an antimicrobial material to kill microbes that contact the surface of the articles.
- Antimicrobial activity is measured by determining the log reduction of infectious bacterial counts after exposure to an antimicrobial substance. For example, a 3-log reduction refers to a 99.9% reduction, and a 4-log reduction refers to a 99.99% reduction.
- a 3-log reduction refers to a 99.9% reduction
- a 4-log reduction refers to a 99.99% reduction.
- the use of antimicrobial coatings on nonwoven materials may be beneficial in reducing the amount of microbes present on the surface, the coating can sometimes compromise the barrier properties of nonwoven materials, thereby increasing the possibility for fluids to penetrate.
- the medical articles are able to kill a high number of microbes, such as a 3 or 4 log reduction (99.9% to 99.99%), within a short period of time, such as under 10 minutes.
- a high number of microbes such as a 3 or 4 log reduction (99.9% to 99.99%)
- a short period of time such as under 10 minutes.
- Such a material would help reduce the transmission of hospital-acquired infections, as the "quick kill" of microbes could break the chain of infection from one surface to another.
- U.S. Patent No. 6,146,651 relates to nonwoven fabrics treated with a biocidal composition including a halogenated phenolic biocide; a water- soluble, film-forming polymer; and at least one surfactant.
- U.S. Patent No. 6,626,873 and U.S. Patent No. 5,772,640 relate to polymeric medical articles comprising chlorhexidine and salts thereof and triclosan.
- U.S. Patent No. 6,626,873 and U.S. Patent No. 5,772,640 refer to medical articles such as catheters, wound drainage tubes, arterial grafts, soft tissue patches, gloves, shunts, stents, tracheal catheters, wound dressings, sutures, guide wires, and prosthetic devices.
- U.S. Patent No. 6,503,952 relates to antimicrobial compositions comprising an antimicrobial such as chlorhexidine free base, chlorhexidine salt, polyhexamethylene biguanide, and alexidine; a quarternary ammonium compound; and a chlorinated phenol compound.
- U.S. Patent Application Publication No. 201 /0150958 relates to antiseptic cleaning agents containing chlorhexidine acetate, a solvent such as alcohol and/or water, and a second biocidal agent such as triclosan.
- a solvent such as alcohol and/or water
- a second biocidal agent such as triclosan
- the present invention is directed to articles comprising a material, such as a nonwoven material, and a coating comprising chlorhexidine acetate and triclosan.
- the articles are preferably medical articles such as gowns, shoe covers, drapes, wraps and caps.
- a coating having a combination of chlorhexidine acetate and triclosan on a material, such as a nonwoven material, has been found to provide effective, fast-acting antimicrobial activity, while minimally affecting the barrier properties of the material.
- the present invention is directed to articles comprising a material, such as a nonwoven material, and a coating comprising
- the articles may be medical articles, such as gowns, shoe covers, drapes, wraps, caps, facial masks, lab coats, or any other article that may be used to prevent the transmission of fluids and/or microbes.
- the material may comprise any fabric or materials, including nonwoven materials or fabrics.
- Nonwoven fabrics refer to a single web, or an assembly or laminate of multiple webs, formed of individual randomly laid fibers, for example using a spunlaid, thermobonded, spunbonded, meltblown or bonded carded web process.
- a laminate of nonwoven fabrics such as a spunbond/meltblown/spunbond (SMS) laminate of polypropylene fibers, is an example of one conventional fabric that could be used in the surgical field.
- SMS spunbond/film/spunbond
- spunlace (hydroentangled) materials may be used.
- the material is about 1 to about 1000 grams per square meter, preferably 10 to 100 grams per square meter, more preferably 20 to 50 grams per square meter (gsm).
- Chlorhexidine acetate also known as chlorhexidine diacetate, is an antimicrobial agent. Chlorhexidine acetate, as well as chlorhexidine free base and other salts of chlorhexidine, such as chlorhexidine gluconate, are effective on gram-positive and gram-negative bacteria and have been found to have both bactericidal and bacteriostatic activity. Surprisingly,
- chlorhexidine acetate in particular, in combination with triclosan has been found to provide effective antimicrobial activity while minimizing the impact on the barrier properties of a material.
- Triclosan also known as 5-chloro-2-(2,4- dichlorophenoxy)phenol and 2,4,4'-trichloro-2'-hydroxy diphenyl ether, is an antimicrobial agent with both antibacterial and antifungal activity.
- the combination of chlorhexidine acetate and triclosan has been found to provide an effective antimicrobial coating on materials, such as nonwoven materials.
- the combination has been found to provide a synergistic effect, providing a high log reduction of bacteria while minimally affecting the barrier properties (fluid permeability) of the materials.
- the combination of chlorhexidine acetate and triclosan has been found to provide effective antimicrobial activity while keeping the material's resistance to fluid penetration, measured using the hydrostatic pressure test, at acceptable levels, compared to each agent alone and compared to other combinations such as chlorhexidine free base and triclosan and chlorhexidine gluconate and triclosan.
- the chlorhexidine acetate and triclosan are present in a chlorhexidine acetate:triclosan ratio, preferably about 25:1 to about 1 :25, more preferably about 10:1 to about 1 :10, even more preferably about 5:1 to about 1 :5, and most preferably about 3:1 to about 1 :3.
- the total amount (dry weight) of the chlorhexidine acetate and triclosan is about 0.1 % to about 70%, preferably 0.25% to 50%, more preferably about 0.35% to 20%, and most preferably about .50% to 10%, of the weight of the coated fabric.
- the chlorhexidine acetate and triclosan may be applied to the materials separately or together.
- the chlorhexidine acetate may be applied first, and then the triclosan may be applied.
- the chlorhexidine acetate and triclosan are combined into one formulation first, and then the combination formulation is applied to the materials.
- a liquid formulation comprising the antimicrobials is prepared and applied to the material.
- the liquid formulation may comprise one or more solvents, such as an alcohol and/or water.
- the liquid formulation comprises the chlorhexidine acetate and triclosan in water and alcohol solutions; preferred alcohols include ethanol, hexanol, or octanol.
- a liquid formulation comprises chlorhexidine acetate (at 0.3% w/w, 0.6% w/w, or 0.75% w/w), triclosan (0.60% w/w), and ethanol (70% w/w).
- the coating of chlorhexidine acetate and triclosan may be applied to the materials in any way.
- a coating solution containing the chlorhexidine acetate and triclosan is sprayed or kiss gravure coated onto a material, such as a nonwoven material.
- the coating may be applied directly to the fibers before bonding.
- the coating is applied after the nonwoven web is formed and bonded.
- Other additives, including but not limited to antistats and coating aids to lower the solution surface tension, may be added to the coating solution.
- the fabric may be dip-coated or may be coated using a dip and squeeze padding process, using a formulation of chlorhexidine acetate and triclosan.
- the coated material may be dried, by air drying or by using dryers.
- dryers For example, air-impingement and flotation dryers may be used.
- the coated material may also be dried by pulling a heated gas, such as air, through the material while pinning the material to a porous surface such as a drum or belt.
- the articles of the present invention have an antimicrobial efficacy of at least a 2 log reduction of bacteria, preferably at least a 3 log reduction, and more preferably at least a 4 log reduction.
- the antimicrobial effect is achieved in less than about 60 minutes, preferably less than about 30 minutes, more preferably less that about 10 minutes, and most preferably less than about 5 minutes.
- the articles of the present invention which comprise coated materials, have similar barrier properties compared to the same materials in uncoated form.
- applying chlorhexidine acetate and triclosan to an SMS nonwoven fabric may decrease the hydrostatic pressure resistance value of the SMS nonwoven fabric (in uncoated form) by no more than about 50%, preferably by no more than about 40%, more preferably by no more than about 30%, and more preferably by no more than about 0 to 10%.
- the hydrostatic pressure of the coated materials is preferably at least 20 cmH 2 0 and more preferably at least 30 cmH 2 0. In some embodiments, for example, when the coated material is used for surgical gowns, the hydrostatic pressure of the coated materials may be preferably at least 50 cmH 2 0.
- the samples were tested for antimicrobial efficacy using AATCC Test Method 100, using gram negative E. co// ATCC #11229 and gram positive S. aureus, MRSA, ATCC #43300. The log reductions of £. col i and MRSA were determined after five minutes.
- the barrier properties of the samples were also tested using the Water Resistance: Hydrostatic Pressure Test, AATCC Test Method 127. Two hydrostatic pressure readings were taken and the values were averaged. The results are listed in the table below.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medical Informatics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Textile Engineering (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Professional, Industrial, Or Sporting Protective Garments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials For Medical Uses (AREA)
- Nonwoven Fabrics (AREA)
Abstract
This invention provides medical articles having antimicrobial efficacy and good barrier properties. In particular, the medical articles comprise a nonwoven material and a coating comprising chlorhexidine acetate and triclosan. The present invention is directed to articles comprising a material, such as a nonwoven material, and a coating comprising chlorhexidine acetate and triclosan. The articles are preferably medical articles such as gowns, shoe covers, drapes, wraps and caps. A coating having a combination of chlorhexidine acetate and triclosan on a material, such as a nonwoven material, has been found to provide effective, fast-acting antimicrobial activity, while minimally affecting the barrier properties of the material.
Description
NONWOVEN MATERIALS CONTAINING CHLORHEXIDINE ACETATE
AND TRICLOSAN
FIELD OF THE INVENTION
[0001] The present invention is directed to medical articles having antimicrobial efficacy and good barrier properties.
BACKGROUND OF THE INVENTION
[0002] In the United States, hospital-acquired infections, also known as nosocomial infections, cause or contribute to almost 100,000 deaths each year. Disposable medical articles, such as gowns, drapes, shoe covers, wraps, and caps are regularly used to minimize the transmission of such infections. These articles are often worn or used for a short period of time, for example less than ten minutes.
[0003] Many of these articles are made with nonwoven materials or fabrics, such as spunbond/meltblown/spunbond (SMS) laminates of polypropylene fibers and can form barriers against microbes and/or fluids. The ability to block the penetration of fluids, such as bodily fluids, is important in a medical environment. Some medical articles, such as medical gowns, are classified into levels of barrier performance based on the AAMI/ANSI PB70 standard, which is a standard developed by the Association for the Advancement of Medical Instrumentation and approved by the American National Standards Institute. In the AAMI/ANSI PB70 standard, the key test for measuring the barrier performance of a material is the Water Resistance: Hydrostatic Pressure Test, AATCC Test Method 127, which was established by the American Association of Textile Chemists and Colorists. The hydrostatic pressure test measures the resistance of a material to the
penetration of water under increasing pressure. There are four levels of barrier performance according to the AAMI/ANSI PB70 standard. Materials having an AAMI Level 1 classification pass a spray impact test and are effective for impact penetration. Examples of materials typically having an AAMI Level 1 classification include basic cover gowns and isolation gowns. Materials having an AAMI Level 2 classification require a hydrostatic pressure of at least 20 cmH20 for water to penetrate through the material. Examples of materials typically having an AAMI Level 2 classification include articles that offer basic protection and are often used when the amount of exposure to fluids is relatively small and for a short period of time. Materials having an AAMI Level 3 classification require a hydrostatic pressure of at least 50 cmH20 for water to penetrate through the material. Examples of materials typically having an AAMI Level 3 classification include articles that offer increased barrier protection and are often used when the amount of fluid exposure is moderate. Materials having an AAMI Level 4 classification are impervious to water passing through. Surgical drapes and gowns often have an AAMI Level 4 classification.
[0004] Some nonwoven materials are coated with an antimicrobial material to kill microbes that contact the surface of the articles. Antimicrobial activity is measured by determining the log reduction of infectious bacterial counts after exposure to an antimicrobial substance. For example, a 3-log reduction refers to a 99.9% reduction, and a 4-log reduction refers to a 99.99% reduction. While the use of antimicrobial coatings on nonwoven materials may be beneficial in reducing the amount of microbes present on
the surface, the coating can sometimes compromise the barrier properties of nonwoven materials, thereby increasing the possibility for fluids to penetrate.
[0005] There is a need in the art for nonwoven materials which have effective barrier properties and which demonstrate fast-acting antimicrobial activity. Preferably, the medical articles are able to kill a high number of microbes, such as a 3 or 4 log reduction (99.9% to 99.99%), within a short period of time, such as under 10 minutes. Such a material would help reduce the transmission of hospital-acquired infections, as the "quick kill" of microbes could break the chain of infection from one surface to another.
[0006] U.S. Patent No. 6,146,651 relates to nonwoven fabrics treated with a biocidal composition including a halogenated phenolic biocide; a water- soluble, film-forming polymer; and at least one surfactant.
[0007] U.S. Patent No. 6,626,873 and U.S. Patent No. 5,772,640 relate to polymeric medical articles comprising chlorhexidine and salts thereof and triclosan. U.S. Patent No. 6,626,873 and U.S. Patent No. 5,772,640 refer to medical articles such as catheters, wound drainage tubes, arterial grafts, soft tissue patches, gloves, shunts, stents, tracheal catheters, wound dressings, sutures, guide wires, and prosthetic devices.
[0008] U.S. Patent No. 6,503,952 relates to antimicrobial compositions comprising an antimicrobial such as chlorhexidine free base, chlorhexidine salt, polyhexamethylene biguanide, and alexidine; a quarternary ammonium compound; and a chlorinated phenol compound.
[0009] U.S. Patent Application Publication No. 201 /0150958 relates to antiseptic cleaning agents containing chlorhexidine acetate, a solvent such as alcohol and/or water, and a second biocidal agent such as triclosan.
[00010] All references cited herein are incorporated by reference in their entirety.
SUMMARY OF THE INVENTION
[00011] The present invention is directed to articles comprising a material, such as a nonwoven material, and a coating comprising chlorhexidine acetate and triclosan. The articles are preferably medical articles such as gowns, shoe covers, drapes, wraps and caps.
[00012] A coating having a combination of chlorhexidine acetate and triclosan on a material, such as a nonwoven material, has been found to provide effective, fast-acting antimicrobial activity, while minimally affecting the barrier properties of the material.
DETAILED DESCRIPTION OF THE INVENTION
[00013] The present invention is directed to articles comprising a material, such as a nonwoven material, and a coating comprising
chlorhexidine acetate and triclosan. The articles may be medical articles, such as gowns, shoe covers, drapes, wraps, caps, facial masks, lab coats, or any other article that may be used to prevent the transmission of fluids and/or microbes.
[00014] In some embodiments, the material may comprise any fabric or materials, including nonwoven materials or fabrics. Nonwoven fabrics refer to a single web, or an assembly or laminate of multiple webs, formed of individual randomly laid fibers, for example using a spunlaid, thermobonded, spunbonded, meltblown or bonded carded web process. A laminate of nonwoven fabrics, such as a spunbond/meltblown/spunbond (SMS) laminate
of polypropylene fibers, is an example of one conventional fabric that could be used in the surgical field. Another example is a spunbond/film/spunbond (SFS) laminate. In some embodiments, spunlace (hydroentangled) materials may be used. In some embodiments, the material is about 1 to about 1000 grams per square meter, preferably 10 to 100 grams per square meter, more preferably 20 to 50 grams per square meter (gsm).
[00015] Chlorhexidine acetate, also known as chlorhexidine diacetate, is an antimicrobial agent. Chlorhexidine acetate, as well as chlorhexidine free base and other salts of chlorhexidine, such as chlorhexidine gluconate, are effective on gram-positive and gram-negative bacteria and have been found to have both bactericidal and bacteriostatic activity. Surprisingly,
chlorhexidine acetate in particular, in combination with triclosan, has been found to provide effective antimicrobial activity while minimizing the impact on the barrier properties of a material.
[00016] Triclosan, also known as 5-chloro-2-(2,4- dichlorophenoxy)phenol and 2,4,4'-trichloro-2'-hydroxy diphenyl ether, is an antimicrobial agent with both antibacterial and antifungal activity.
[00017] The combination of chlorhexidine acetate and triclosan has been found to provide an effective antimicrobial coating on materials, such as nonwoven materials. The combination has been found to provide a synergistic effect, providing a high log reduction of bacteria while minimally affecting the barrier properties (fluid permeability) of the materials. In particular, the combination of chlorhexidine acetate and triclosan has been found to provide effective antimicrobial activity while keeping the material's resistance to fluid penetration, measured using the hydrostatic pressure test,
at acceptable levels, compared to each agent alone and compared to other combinations such as chlorhexidine free base and triclosan and chlorhexidine gluconate and triclosan.
[00018] In some embodiments, the chlorhexidine acetate and triclosan are present in a chlorhexidine acetate:triclosan ratio, preferably about 25:1 to about 1 :25, more preferably about 10:1 to about 1 :10, even more preferably about 5:1 to about 1 :5, and most preferably about 3:1 to about 1 :3. In some embodiments, the total amount (dry weight) of the chlorhexidine acetate and triclosan is about 0.1 % to about 70%, preferably 0.25% to 50%, more preferably about 0.35% to 20%, and most preferably about .50% to 10%, of the weight of the coated fabric.
[00019] The chlorhexidine acetate and triclosan may be applied to the materials separately or together. For example, in some embodiments, the chlorhexidine acetate may be applied first, and then the triclosan may be applied. In some embodiments, the chlorhexidine acetate and triclosan are combined into one formulation first, and then the combination formulation is applied to the materials. In some embodiments, a liquid formulation comprising the antimicrobials is prepared and applied to the material. The liquid formulation may comprise one or more solvents, such as an alcohol and/or water. Examples of solvents include, but are not limited to water, ethanol, hexanol, acetone, isopropanol, benzyl alcohol, propylene glycol, glycerol, and polyethylene glycol. In some preferred embodiments, the liquid formulation comprises the chlorhexidine acetate and triclosan in water and alcohol solutions; preferred alcohols include ethanol, hexanol, or octanol.
One example of a liquid formulation comprises chlorhexidine acetate (at 0.3% w/w, 0.6% w/w, or 0.75% w/w), triclosan (0.60% w/w), and ethanol (70% w/w).
[00020] The coating of chlorhexidine acetate and triclosan may be applied to the materials in any way. Preferably, a coating solution containing the chlorhexidine acetate and triclosan is sprayed or kiss gravure coated onto a material, such as a nonwoven material. The coating may be applied directly to the fibers before bonding. In preferred embodiments, the coating is applied after the nonwoven web is formed and bonded. Other additives, including but not limited to antistats and coating aids to lower the solution surface tension, may be added to the coating solution. In other embodiments, the fabric may be dip-coated or may be coated using a dip and squeeze padding process, using a formulation of chlorhexidine acetate and triclosan.
[00021] After the application of the coating, the coated material may be dried, by air drying or by using dryers. For example, air-impingement and flotation dryers may be used. The coated material may also be dried by pulling a heated gas, such as air, through the material while pinning the material to a porous surface such as a drum or belt.
[00022] In some embodiments, the articles of the present invention have an antimicrobial efficacy of at least a 2 log reduction of bacteria, preferably at least a 3 log reduction, and more preferably at least a 4 log reduction. In some embodiments, the antimicrobial effect is achieved in less than about 60 minutes, preferably less than about 30 minutes, more preferably less that about 10 minutes, and most preferably less than about 5 minutes.
[00023] In some embodiments, the articles of the present invention, which comprise coated materials, have similar barrier properties compared to
the same materials in uncoated form. For example, in some embodiments, applying chlorhexidine acetate and triclosan to an SMS nonwoven fabric may decrease the hydrostatic pressure resistance value of the SMS nonwoven fabric (in uncoated form) by no more than about 50%, preferably by no more than about 40%, more preferably by no more than about 30%, and more preferably by no more than about 0 to 10%.
[00024] In some embodiments, the hydrostatic pressure of the coated materials (as measured by, for example, the Water Resistance: Hydrostatic Pressure Test, AATCC Test Method 127) is preferably at least 20 cmH20 and more preferably at least 30 cmH20. In some embodiments, for example, when the coated material is used for surgical gowns, the hydrostatic pressure of the coated materials may be preferably at least 50 cmH20.
EXAMPLE
[00025] An experiment was conducted to compare the effect of the combination of chlorhexidine acetate (CHA) and triclosan, to: (1) each of chlorhexidine free base (CH), chlorhexidine acetate, chlorhexidine gluconate (CHG), polyhexamethylene biguanide (PHMB), and triclosan alone, (2) each of the combinations of CH and triclosan, CHG and triclosan, and PHMB and triclosan. The following coating formulations were prepared with deionized water and sprayed onto 8X8 inch fabric swatches of a 34 gsm spunbond/meltblown/spunbond (SMS) nonwoven material using disposable atomizing hand sprayers.
- Formulation A: CHA (0.6% w/w), triclosan (0.60% w/w), and ethanol (70%)
- Formulation B: CHA (0.3% w/w), triclosan (0.60% w/w), and ethanol (70%)
- Formulation C: CHA (0.75% w/w), triclosan (0.60% w/w), and ethanol (70%)
- Formulation D: control with no coating
- Formulation E: ethanol (70%)
- Formulation F: CH (0.30% w/w) and ethanol (70%)
- Formulation G: CH (0.60% w/w) and ethanol (70%)
- Formulation H: CH (1.20% w/w) and ethanol (70%)
- Formulation I: CHA (0.30% w/w) and ethanol (70%)
- Formulation J: CHA (0.30% w/w) and ethanol (70%)
- Formulation K: CHG (1.0% w/w) and hexanol (0.6%)
- Formulation L: CHG (1.0% w/w) and hexanol (0.6%)
- Formulation M: PHMB (1.0% w/w) and ethanol (70%)
- Formulation N: PHMB (1.0% w/w) and hexanol (0.6%)
- Formulation O: Triclosan (0.3% w/w) and ethanol (70%)
- Formulation P: Triclosan (0.6% w/w) and ethanol (70%)
- Formulation Q: CH (0.30% w/w), Triclosan (0.6% w/w) and ethanol (70%)
- Formulation R: CH (0.60% w/w), Triclosan (0.6% w/w) and ethanol (70%)
- Formulation S: CHG (0.35% w/w), Triclosan (0.6% w/w) and ethanol (70%)
- Formulation T: PHMB (0.15% w/w), Triclosan (0.6% w/w) and ethanol (70%)
- Formulation U: PHMB (0.45% w/w), Triclosan (0.6% w/w) and ethanol (70%)
- Formulation V: PHMB (0.75% w/w), Triclosan (0.6% w/w) and ethanol (70%)
[00026] The formulations were sprayed onto the fabric swatches until the swatches were uniformly saturated. The saturation point was determined visually as the coating formulation wetted the fabric swatches, causing them to become translucent when fully saturated. The swatches were then placed
horizontally on a wire rack and air dried in a fume hood. In some cases, the samples were placed in an oven for drying.
[00027] The samples were tested for antimicrobial efficacy using AATCC Test Method 100, using gram negative E. co// ATCC #11229 and gram positive S. aureus, MRSA, ATCC #43300. The log reductions of £. col i and MRSA were determined after five minutes. The barrier properties of the samples were also tested using the Water Resistance: Hydrostatic Pressure Test, AATCC Test Method 127. Two hydrostatic pressure readings were taken and the values were averaged. The results are listed in the table below.
[00028] The results show that the combination of chlorhexidine acetate and triclosan on the SMS nonwoven material demonstrated high log reductions of both E. coli and MRSA, which shows effective antimicrobial activity. In addition, the barrier properties of the coated SMS nonwoven material, measured by the hydrostatic pressure test, were maintained at a high value. In contrast, samples coated with the individual antimicrobial agents alone or with other combinations of antimicrobials demonstrated good antimicrobial activity but poor barrier properties, good barrier properties but poor antimicrobial activity, or both poor antimicrobial activity and poor barrier properties. For example, for samples coated with just triclosan, the barrier properties of the fabric were high, but the antimicrobial activity was very low. For samples coated with just chlorhexidine free base, the antimicrobial efficacy was high, but the barrier properties were poor. In addition, samples coated with just chlorhexidine acetate demonstrated poor barrier properties and poor antimicrobial activity against MRSA.
TABLE
Claims
Claim 1. An article comprising a nonwoven material and a coating comprising chlorhexidine acetate and triclosan.
Claim 2 The article of claim 1 , wherein the nonwoven material comprises spunbond meltblown spunbond polypropylene.
Claim 3. The article of claim 1 , wherein the coating comprises
chlorhexidine acetate and triclosan in a ratio of about 25:1 to about 1 :25.
Claim 4. The article of claim 1 , wherein the coating comprises
chlorhexidine acetate and triclosan in a ratio of about 5:1 to about 1 :5.
Claim 5. The article of claim 1 , wherein the coating comprises
chlorhexidine acetate and triclosan in a ratio of about 3:1 to about 1 :3.
Claim 6. The article of claim 1 , wherein the article is a medical article selected from the group consisting of: gowns, shoe covers, drapes, wraps, caps, lab coats and face masks.
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| AU2013281226A AU2013281226A1 (en) | 2012-06-25 | 2013-03-15 | Nonwoven materials containing chlorhexidine acetate and triclosan |
| BR112014031870A BR112014031870A2 (en) | 2012-06-25 | 2013-03-15 | non-woven materials with chlorhexidine acetate and triclosan |
| MX2014015470A MX2014015470A (en) | 2012-06-25 | 2013-03-15 | Nonwoven materials containing chlorhexidine acetate and triclosan. |
| CA 2876574 CA2876574A1 (en) | 2012-06-25 | 2013-03-15 | Nonwoven materials containing chlorhexidine acetate and triclosan |
| EP13809079.0A EP2863964A4 (en) | 2012-06-25 | 2013-03-15 | Nonwoven materials containing chlorhexidine acetate and triclosan |
| CN201380032117.1A CN104507512A (en) | 2012-06-25 | 2013-03-15 | Nonwoven materials containing chlorhexidine acetate and triclosan |
| IN38DEN2015 IN2015DN00038A (en) | 2012-06-25 | 2013-03-15 | |
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| IL236328A IL236328A0 (en) | 2012-06-25 | 2014-12-17 | Nonwoven materials containing chlorhexidine acetate and triclosan |
| PH12014502824A PH12014502824A1 (en) | 2012-06-25 | 2014-12-18 | Nonwoven materials containing chlorhexidine acetate and triclosan |
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| EP3694439A4 (en) | 2017-10-12 | 2021-12-15 | Medline Industries, Inc. | Antiseptic wipes |
| WO2019087124A1 (en) * | 2017-11-01 | 2019-05-09 | Clexio Biosciences Ltd. | Finished fibrous structures and methods of their use and preparation |
| CN111345288A (en) * | 2020-03-12 | 2020-06-30 | 优仕康生（天津）科技发展有限公司 | A colloidal carrier capable of forming antibacterial and antiviral coating on the surface of respiratory protector, colloidal tincture and application thereof |
| EP3978038A1 (en) | 2020-10-04 | 2022-04-06 | Elke Münch | Mobile device operable by means of a temperature difference for cleaning and disinfecting room air and test device for same |
| DE102020125921B4 (en) | 2020-10-04 | 2022-05-19 | Elke Münch | Mobile device for cleaning and disinfecting room air that can be operated by a temperature difference |
| DE102020125922B4 (en) | 2020-10-04 | 2022-06-02 | Elke Münch | Mobile device for cleaning and disinfecting room air |
| EP3981442A1 (en) | 2020-10-04 | 2022-04-13 | Elke Münch | Mobile device operable by means of a temperature difference for cleaning and disinfecting room air |
| DE102020125919B4 (en) | 2020-10-04 | 2022-06-23 | Elke Münch | Mobile device that can be operated by a temperature difference for cleaning and disinfecting room air and a test device therefor |
| DE102020125920B4 (en) | 2020-10-04 | 2022-05-19 | Elke Münch | Mobile device for cleaning and disinfecting room air that can be operated by a temperature difference |
| DE102020006520A1 (en) | 2020-10-24 | 2022-04-28 | Magnetic Hyperthermia Solutions B.V. | Device and method for attenuating and/or killing microorganisms, viruses and virions |
| IT202000027864A1 (en) * | 2020-11-23 | 2022-05-23 | Mario Carnevali | USE OF CHLORHEXIDINE FOR THE CREATION AND USE OF VIRUCIDIAL CHEMICAL FILTERS AGAINST CORONAVIRUS CONTAGION (COVID-19) WHICH RETURN AND/OR PRODUCE AIR DECONTAMINATED BY VIRUSES, FOR MASKS, FACE MASKS, AND AIR TREATMENT SYSTEMS OF ANY KIND. |
| CN112323493A (en) * | 2020-11-28 | 2021-02-05 | 无锡市丹怡纺织品有限公司 | Preparation method of antibacterial woolen overcoat |
| DE102022001868A1 (en) | 2022-05-29 | 2023-11-30 | Elke Hildegard Münch | Biocide-coated, reticulated plastic foams, process for their production and their use |
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| US5161686A (en) * | 1989-04-14 | 1992-11-10 | Kimberly-Clark Corporation | Odor-absorbing web material and medical material packages containing the web material |
| US20110150958A1 (en) * | 2009-12-22 | 2011-06-23 | Becton, Dickinson And Company | Chlorhexidine acetate antiseptic cleaning agent |
| US20110305898A1 (en) * | 2010-06-09 | 2011-12-15 | Zheng Zhang | Non-fouling, anti-microbial, anti-thrombogenic graft compositions |
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| US4343853A (en) * | 1980-03-06 | 1982-08-10 | Morrison Willard L | Antimicrobially treated fabric construction |
| US5213881A (en) * | 1990-06-18 | 1993-05-25 | Kimberly-Clark Corporation | Nonwoven web with improved barrier properties |
| US5561863A (en) * | 1994-10-04 | 1996-10-08 | Kimberly-Clark Corporation | Surgical face mask |
| US5772640A (en) * | 1996-01-05 | 1998-06-30 | The Trustees Of Columbia University Of The City Of New York | Triclosan-containing medical devices |
| US6596657B1 (en) * | 1999-02-17 | 2003-07-22 | Poly-Med, Inc. | Antimicrobial fabrics |
| US20070048345A1 (en) * | 2005-08-31 | 2007-03-01 | Kimberly-Clark Worldwide, Inc. | Antimicrobial composition |
| US20070048356A1 (en) * | 2005-08-31 | 2007-03-01 | Schorr Phillip A | Antimicrobial treatment of nonwoven materials for infection control |
-
2013
- 2013-03-15 AU AU2013281226A patent/AU2013281226A1/en not_active Abandoned
- 2013-03-15 MX MX2014015470A patent/MX2014015470A/en unknown
- 2013-03-15 JP JP2015518394A patent/JP2015528069A/en active Pending
- 2013-03-15 BR BR112014031870A patent/BR112014031870A2/en not_active IP Right Cessation
- 2013-03-15 KR KR20157000013A patent/KR20150023618A/en not_active Application Discontinuation
- 2013-03-15 IN IN38DEN2015 patent/IN2015DN00038A/en unknown
- 2013-03-15 CA CA 2876574 patent/CA2876574A1/en not_active Abandoned
- 2013-03-15 CN CN201380032117.1A patent/CN104507512A/en active Pending
- 2013-03-15 WO PCT/US2013/032506 patent/WO2014003858A1/en active Application Filing
- 2013-03-15 EP EP13809079.0A patent/EP2863964A4/en not_active Withdrawn
- 2013-03-15 US US13/840,615 patent/US20130344122A1/en not_active Abandoned
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2014
- 2014-12-17 IL IL236328A patent/IL236328A0/en unknown
- 2014-12-18 PH PH12014502824A patent/PH12014502824A1/en unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5161686A (en) * | 1989-04-14 | 1992-11-10 | Kimberly-Clark Corporation | Odor-absorbing web material and medical material packages containing the web material |
| US20110150958A1 (en) * | 2009-12-22 | 2011-06-23 | Becton, Dickinson And Company | Chlorhexidine acetate antiseptic cleaning agent |
| US20110305898A1 (en) * | 2010-06-09 | 2011-12-15 | Zheng Zhang | Non-fouling, anti-microbial, anti-thrombogenic graft compositions |
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| EP2863964A4 (en) | 2016-01-13 |
| KR20150023618A (en) | 2015-03-05 |
| US20130344122A1 (en) | 2013-12-26 |
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| IN2015DN00038A (en) | 2015-05-22 |
| CA2876574A1 (en) | 2014-01-03 |
| EP2863964A1 (en) | 2015-04-29 |
| PH12014502824A1 (en) | 2015-02-02 |
| JP2015528069A (en) | 2015-09-24 |
| IL236328A0 (en) | 2015-02-26 |
| BR112014031870A2 (en) | 2017-06-27 |
| CN104507512A (en) | 2015-04-08 |
| MX2014015470A (en) | 2015-03-06 |
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