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EP1156766A4 - Garniture intrinsequement absorbante et procede de fabrication - Google Patents

Garniture intrinsequement absorbante et procede de fabrication

Info

Publication number
EP1156766A4
EP1156766A4 EP99966054A EP99966054A EP1156766A4 EP 1156766 A4 EP1156766 A4 EP 1156766A4 EP 99966054 A EP99966054 A EP 99966054A EP 99966054 A EP99966054 A EP 99966054A EP 1156766 A4 EP1156766 A4 EP 1156766A4
Authority
EP
European Patent Office
Prior art keywords
dressing
antimicrobial
recited
polymer matrix
polymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99966054A
Other languages
German (de)
English (en)
Other versions
EP1156766A1 (fr
Inventor
Christopher D Batich
Gregory S Schultz
Bruce A Mast
Gerald M Olderman
David Lerner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Quick Med Technologies Inc
University of Florida Research Foundation Inc
Original Assignee
University of Florida
Quick Med Technologies Inc
University of Florida Research Foundation Inc
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 University of Florida, Quick Med Technologies Inc, University of Florida Research Foundation Inc filed Critical University of Florida
Publication of EP1156766A1 publication Critical patent/EP1156766A1/fr
Publication of EP1156766A4 publication Critical patent/EP1156766A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/15—Absorbent pads, e.g. sanitary towels, swabs or tampons for external or internal application to the body; Supporting or fastening means therefor; Tampon applicators
    • A61F13/84—Accessories, not otherwise provided for, for absorbent pads
    • A61F13/8405—Additives, e.g. for odour, disinfectant or pH control

Definitions

  • This invention relates generally to absorbent dressings, and more particularly highly- absorbent synthetic polymer dressings having antimicrobial agents attached thereto.
  • wound dressings In the area of wound dressings, bacterial contarnination of acute wounds and infection of chronic skin wounds are major clinical problems that can result in significant morbidity and, in severe cases, mortality.
  • wound dressings have been designed to absorb wound fluids and yet provide a moist environment for promoting wound healing.
  • moist environments create a nutrient rich reservoir for bacterial growth in the dressing. Bacteria growing in the dressing can be shed back into the wound, increasing the risk of wound infection, or response to toxins, and producing strong, foul odors.
  • antibiotics or chemical disinfectants are frequently applied topically to wounds prior to covering the wound with a dressing.
  • topical agents are sometimes applied directly to the surface of the dressing.
  • some known dressings incorporate charcoal powder to absorb molecules generating the foul odor.
  • topical application of antibacterial agents is net d sirable. 5cr instance, tac'.ericid ⁇ i agents applied lopically to vcund irsM ff igs >.av ⁇ a tendency to seep into the wound being created.
  • many antimicrobial drugs, such as iodine are cytotoxic and will retard wound healing if used repetitively or at high concentrations.
  • a composition comprising a superabsorbent polymer having a monolayer (or near monolayer) of silane antimicrobial agent in a covalent bonding relationship with the base polymer is disclosed in U.S. Patent No. 5 ,045,322.
  • the composition may be in the form of flakes, strips, powders, filaments, fibers or films, and may be applied to a substrate in the form of a coating.
  • the aforementioned composition is less apt to enter a wound vis-a-vis conventional topical treatment systems.
  • the disclosed composition provides an improvement over conventional topical treatment systems.
  • silanes contain siioxane bonds which can be cleaved by acids and bases produced by infection or bacterial growth. In turn, these reactions may weaken or destroy bonds between die silane antimicrobial agent and the underlying polymer. Consequently, antimicrobial agent may seep into a wound and retard wound healing.
  • the composition comprises a polymer matrix having quaternary ammonium groups tethered to its surface through non- s ⁇ oxane bonds.
  • the surface area of the polymer matrix is enhanced, for instance, by electrostatically spinning a fiber-forming synthetic polymer to form a f ayed fiber or filament.
  • the polymer solution can be wet- or dry-spun to create a roughened fiber surface by controlling the choice of solvent and the polymer solution temperature. Additional surface area enhancement is provided by tethering molecular chains of quaternary ammonium pendent groups to the surface of the polymer matrix. Tethering may be accomplished by known techniques such as grafting and selective adsorption.
  • non-ionic bactericidal molecules are coupled to the surface of the polymer matrix, in lieu of ionically-charged molecules.
  • Ionically-charged molecules are prone to being neutralized upon encountering oppositely- charged molecules.
  • positively-charged quaternary ammonium groups may be neutralized by negatively-charged chloride ions present in physiological fluids.
  • non-ionic surface groups may be preferable.
  • Detailed Dft ⁇ g ⁇ ptiQn of the refer ⁇ F.mhod ⁇ nfs A novel antibacterial polymer composition is fabricated to have an enhanced surface area and superabsorbent capacity for biological fluids, including urine, blood, and wound
  • the composition includes a polymer matrix having quaternary ammonium compounds attached to the surface of the polymer matrix.
  • the polymer matrix is comprised of a plurality of hydrophilic fibers or filaments which can be fabricated in any suitable manner.
  • suitable fibers or filaments can be fabricated by wet- or dry-spinning a fiber-forming synthetic polymer from a spinning solvent.
  • the resulting polymer has superabsorbent capacity.
  • polymers capable of absorbing from about thirty to sixty grams of water per gram of polymer are considered to be superabsorbent.
  • Examples of superabsorbent polymers which can be fabricated in this manner include poiyacrylic acids, polyethylene oxides and polyvinyl alcohols. For example, methods for spinning polyethylene oxide using acetone solvent are well known.
  • the polymer matrix is fabricated to have an enhanced surface area. Enhancing the surface area of the polymer matrix results in improved absorption of biological fluids, and increases the availability of sites for attachment of the antimicrobial quaternary ammonium compounds. A corresponding increase in the quantity and density of antimicrobial sites, in turn, enhances the efficacy of the composition in killing organisms such as bacteria and viruses.
  • surface area enhancement is accomplished by a modified spinning or casting method.
  • electrostatic spinning is a modified spinning technique which results in fraying of the fiber as it exits the spinere te.
  • a polymer solution can be wet- or dry-spun to create a roughened fiber surface by controlling the solvent type and the polymer solution temperature. This technology is well known and has been applied, for example, in the manufacture of asymmetric membranes having roughened pores for dialysis. The size of the roughened pores is primarily controlled by the speed of precipitation which, in turn, is controlled by solvent interaction parameters, temperature, etc.
  • the surface area of the polymer composition is further enha ⁇ csd by tethering chains of an ⁇ crcbiai groups to the outer s rrace ci " the individual polymer fibers.
  • Fraiex d biy, molecular chains of quaternary ammonium pendent groups are fabricated to have at least c ⁇ c end adapted for attachment to a fiber surface.
  • suri ce grafting may be accomplished by creating surface free radicals as initiation sites from peroxide generation (ozone or microwave).
  • surface attachment of an mterpenetrating network may be achieved using a monomer which swells the substrate polymer.
  • the incorporation of tethered antimicrobial chains has the further benefit of enhancing the functionality of the composition.
  • the tethered antimicrobial chains extend into the particular biological solution to bind to harmful bacterial and viral organisms.
  • the chain structures of the present invention which function like arms extending outwardly from the fiber surface, more effectively bind the antimicrobial sites to harmful organisms.
  • tethering is accomplished by grafting the antimicrobial chains directly to the matrix surface, or by selective adsorption of a copolymer to the matrix surface.
  • grafting techniques are well known in the art For example, quaternary- ammonium compound grafting using the monomer trir ⁇ emylanunonium ethyl met acrylate to graft polymerize to a modified polyethylene surface is described by Yahaioui (Master's Thesis, University of Florida, 1986). Yahioui describes a grafting technique in which a plasma discharge is used to create free radicals which initiate polymerization of appropriate monomers. Selective adsorption of appropriate block c ⁇ p ⁇ ly ers can also be used.
  • the present invention incorporates a chemical structure which is based on polymerization (e., surface grafting) of monomers containing all carbon-carbo ⁇ , carbon-oxygen and carboa- ⁇ itrogen main bonds, such as the dialkly, diallyl, quaternary ammonium compounds. Consequently, the composition of the present invention results in a structure which is less prone to reacting with acids and bases produced by bacterial growth. As previously mentioned, such reactions can degrade the attachment between the matrix and antimicrobial groups. In instances where the composition is ip ilad ' .o a wound dr ⁇ ssi ⁇ g. suc degradation ⁇ cui ⁇ rssuic in antimicrobial ⁇ genis detaching from the polymer matrix and entering a wound site. In some cases, this can have the deleterious effect of retarding wound healing.
  • anionic antibacteri ⁇ dal groups are immobilized on the surface of a supexabsorbant dressing to improve the antibactericid.il efficacy of the dressing.
  • the positive charge associated with quaternary ammonium groups can be neutralized by negative ions, such as chloride ions present in physiological fluids such as urine and plasma.
  • anionic surface groups can be substituted for quaternary ammonium groups. Examples of chemical compounds that can be used to produce immobilized anionic surface groups include Triton-100, Tween 20 and deoxych ⁇ late.
  • Triton- 100 contains a free hydroxyl group which can be derivatized into a good leaving group, such as tosyl or chloride, and subsequently reacted with a base-treated polymer, such as methyl cellulose, to yield a surface immobilized non-ionic surfac'ant
  • Dimethyldiallyl ammonium chloride is one example of a suitable monomer which may be used with the present invention.
  • This monomer commonly referred to as B DAC or
  • DADMAC is used in the fabrication of commercial flocculating polymers. Modifications of trialkyl(p-vinylbenzyl) ammonium chloride or the p-trialkylaminoethyl styrene monomers are also suitable. One such example is trimethyl(p-vinyl benzyl) ammonium chloride; the methyl groups of this monomer can be replaced by other alkyl groups to impart desired properties. Alternatively, methacrylate-based monomers may be used; however, they may suffer from hydr ⁇ lytic instability under acidic and basic conditions in a fashion similar to the silane-based treatments of the prior art. Consequently, methacrylate-based monomers are not preferred.

Landscapes

  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Materials For Medical Uses (AREA)
  • Absorbent Articles And Supports Therefor (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)
  • Orthopedics, Nursing, And Contraception (AREA)

Abstract

Garniture polymère superabsorbante présentant des propriétés antimicrobiennes, utile pour fabriquer des pansements, des serviettes hygiéniques, des tampons et analogue, qui comporte une matrice polymère synthétique élaborée de manière à présenter une surface accrue. Des composés antimicrobiens sont couplés à la surface de la matrice polymère par des liaisons non siloxane.
EP99966054A 1998-12-08 1999-12-08 Garniture intrinsequement absorbante et procede de fabrication Withdrawn EP1156766A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11147298P 1998-12-08 1998-12-08
US111472P 1998-12-08
PCT/US1999/029091 WO2000033778A1 (fr) 1998-12-08 1999-12-08 Garniture intrinsequement absorbante et procede de fabrication

Publications (2)

Publication Number Publication Date
EP1156766A1 EP1156766A1 (fr) 2001-11-28
EP1156766A4 true EP1156766A4 (fr) 2005-01-12

Family

ID=22338754

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99966054A Withdrawn EP1156766A4 (fr) 1998-12-08 1999-12-08 Garniture intrinsequement absorbante et procede de fabrication

Country Status (11)

Country Link
EP (1) EP1156766A4 (fr)
JP (1) JP2003527145A (fr)
KR (1) KR100689020B1 (fr)
CN (1) CN1183970C (fr)
AU (1) AU773532B2 (fr)
CA (1) CA2353436C (fr)
EA (1) EA004160B1 (fr)
ID (1) ID30081A (fr)
MX (1) MXPA01005773A (fr)
OA (1) OA11725A (fr)
WO (1) WO2000033778A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7709694B2 (en) 1998-12-08 2010-05-04 Quick-Med Technologies, Inc. Materials with covalently-bonded, nonleachable, polymeric antimicrobial surfaces
WO2004076770A1 (fr) 2003-02-25 2004-09-10 Quick-Med Technologies, Inc. Plaque de platre antifongique amelioree
DE202004017465U1 (de) 2004-11-10 2005-12-15 Riesinger, Birgit Einweg-Absorptionskörper zum Anschluss an Haut- und Schleimhautoberflächen des menschlichen Körpers
BRPI0617099B1 (pt) * 2005-08-22 2018-06-05 University Of Florida Research Foundation, Inc. Método de fabricação de um material inerentemente antimicrobiano
WO2007025178A2 (fr) * 2005-08-26 2007-03-01 New York University Compositions multimeres polyvalentes contenant des polypeptides actifs, compositions pharmaceutiques et procedes utilisant celles-ci
WO2012065610A1 (fr) 2010-11-18 2012-05-24 Vestergaard Frandsen Sa Procédé et substrat avec revêtement « quat »
US10245025B2 (en) 2012-04-06 2019-04-02 Ethicon, Inc. Packaged antimicrobial medical device having improved shelf life and method of preparing same
US9566363B2 (en) * 2013-05-17 2017-02-14 Shakthi Knitting Limited Microbicidal composite material
GB201410510D0 (en) * 2014-06-12 2014-07-30 Fantex Ltd Liquid Antimicrobial
US12421396B2 (en) * 2021-03-25 2025-09-23 Fujifilm Business Innovation Corp. Silica particles and method for producing the same

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4027020A (en) * 1974-10-29 1977-05-31 Millmaster Onyx Corporation Randomly terminated capped polymers
US4810567A (en) * 1985-08-21 1989-03-07 Uop Antimicrobial fabrics utilizing graft copolymers
US4929498A (en) * 1989-01-31 1990-05-29 James River Corporation Of Virginia Engineered-pulp wet wiper fabric
US5035892A (en) * 1988-05-09 1991-07-30 Dow Corning Corporation Antimicrobial superabsorbent compositions and methods
EP0525751A1 (fr) * 1991-07-30 1993-02-03 Hymo Corporation Procédé de préparation d'une dispersion d'un monomère cationique soluble dans l'eau
EP0656372A1 (fr) * 1991-10-31 1995-06-07 KOHJIN CO. Ltd. Agent de deshydratation de boues
EP0839841A2 (fr) * 1996-10-31 1998-05-06 Sanyo Chemical Industries, Ltd. Agent antibactérien absorbant l'eau et matériau antibactérien absorbant l'eau
WO1999032157A2 (fr) * 1997-12-23 1999-07-01 Biosafe, Inc. Procede de creation d'un agent biostatique au moyen de polymeres reticules enchevetres

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4027020A (en) * 1974-10-29 1977-05-31 Millmaster Onyx Corporation Randomly terminated capped polymers
US4810567A (en) * 1985-08-21 1989-03-07 Uop Antimicrobial fabrics utilizing graft copolymers
US5035892A (en) * 1988-05-09 1991-07-30 Dow Corning Corporation Antimicrobial superabsorbent compositions and methods
US4929498A (en) * 1989-01-31 1990-05-29 James River Corporation Of Virginia Engineered-pulp wet wiper fabric
EP0525751A1 (fr) * 1991-07-30 1993-02-03 Hymo Corporation Procédé de préparation d'une dispersion d'un monomère cationique soluble dans l'eau
EP0656372A1 (fr) * 1991-10-31 1995-06-07 KOHJIN CO. Ltd. Agent de deshydratation de boues
EP0839841A2 (fr) * 1996-10-31 1998-05-06 Sanyo Chemical Industries, Ltd. Agent antibactérien absorbant l'eau et matériau antibactérien absorbant l'eau
WO1999032157A2 (fr) * 1997-12-23 1999-07-01 Biosafe, Inc. Procede de creation d'un agent biostatique au moyen de polymeres reticules enchevetres

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO0033778A1 *

Also Published As

Publication number Publication date
EA004160B1 (ru) 2004-02-26
WO2000033778A1 (fr) 2000-06-15
CA2353436C (fr) 2008-01-08
CN1183970C (zh) 2005-01-12
KR100689020B1 (ko) 2007-03-09
CN1348346A (zh) 2002-05-08
CA2353436A1 (fr) 2000-06-15
EP1156766A1 (fr) 2001-11-28
KR20010105307A (ko) 2001-11-28
JP2003527145A (ja) 2003-09-16
OA11725A (en) 2005-01-25
WO2000033778A9 (fr) 2001-11-15
ID30081A (id) 2001-11-01
EA200100521A1 (ru) 2002-02-28
AU2169500A (en) 2000-06-26
AU773532B2 (en) 2004-05-27
MXPA01005773A (es) 2004-04-02

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