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WO2000033778A1 - Garniture intrinsequement absorbante et procede de fabrication - Google Patents

Garniture intrinsequement absorbante et procede de fabrication Download PDF

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Publication number
WO2000033778A1
WO2000033778A1 PCT/US1999/029091 US9929091W WO0033778A1 WO 2000033778 A1 WO2000033778 A1 WO 2000033778A1 US 9929091 W US9929091 W US 9929091W WO 0033778 A1 WO0033778 A1 WO 0033778A1
Authority
WO
WIPO (PCT)
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.)
Ceased
Application number
PCT/US1999/029091
Other languages
English (en)
Other versions
WO2000033778A9 (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.)
University of Florida
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
Priority to CA002353436A priority Critical patent/CA2353436C/fr
Priority to JP2000586273A priority patent/JP2003527145A/ja
Priority to AU21695/00A priority patent/AU773532B2/en
Priority to US09/857,906 priority patent/US7045673B1/en
Priority to EP99966054A priority patent/EP1156766A4/fr
Priority to EA200100521A priority patent/EA004160B1/ru
Priority to MXPA01005773A priority patent/MXPA01005773A/es
Application filed by University of Florida, Quick Med Technologies Inc, University of Florida Research Foundation Inc filed Critical University of Florida
Publication of WO2000033778A1 publication Critical patent/WO2000033778A1/fr
Anticipated expiration legal-status Critical
Priority to US09/965,740 priority patent/US7709694B2/en
Publication of WO2000033778A9 publication Critical patent/WO2000033778A9/fr
Priority to US10/786,959 priority patent/US20050033251A1/en
Priority to US12/772,686 priority patent/US8333743B2/en
Ceased 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)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Materials For Medical Uses (AREA)
  • Absorbent Articles And Supports Therefor (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)
  • Orthopedics, Nursing, And Contraception (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (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.
PCT/US1999/029091 1998-12-08 1999-12-08 Garniture intrinsequement absorbante et procede de fabrication Ceased WO2000033778A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
MXPA01005773A MXPA01005773A (es) 1998-12-08 1999-12-08 Vendaje absorbente inherentemente bactericida y metodo de fabricacion.
AU21695/00A AU773532B2 (en) 1998-12-08 1999-12-08 Intrinsically bactericidal absorbent dressing and method of fabrication
US09/857,906 US7045673B1 (en) 1998-12-08 1999-12-08 Intrinsically bactericidal absorbent dressing and method of fabrication
EP99966054A EP1156766A4 (fr) 1998-12-08 1999-12-08 Garniture intrinsequement absorbante et procede de fabrication
EA200100521A EA004160B1 (ru) 1998-12-08 1999-12-08 Бактерицидная абсорбирующая повязка и способ ее изготовления
CA002353436A CA2353436C (fr) 1998-12-08 1999-12-08 Garniture intrinsequement absorbante et procede de fabrication
JP2000586273A JP2003527145A (ja) 1998-12-08 1999-12-08 本質的に殺菌性の吸収性当て物及びその製造法
US09/965,740 US7709694B2 (en) 1998-12-08 2001-09-28 Materials with covalently-bonded, nonleachable, polymeric antimicrobial surfaces
US10/786,959 US20050033251A1 (en) 1998-12-08 2004-02-25 Controlled release of biologically active substances from select substrates
US12/772,686 US8333743B2 (en) 1998-12-08 2010-05-03 Antimicrobial bandage material comprising superabsorbent and non-superabsorbent layers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11147298P 1998-12-08 1998-12-08
US60/111,472 1998-12-08

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US09/857,906 Continuation-In-Part US7045673B1 (en) 1998-12-08 1999-12-08 Intrinsically bactericidal absorbent dressing and method of fabrication
US09/965,740 Continuation-In-Part US7709694B2 (en) 1998-12-08 2001-09-28 Materials with covalently-bonded, nonleachable, polymeric antimicrobial surfaces

Publications (2)

Publication Number Publication Date
WO2000033778A1 true WO2000033778A1 (fr) 2000-06-15
WO2000033778A9 WO2000033778A9 (fr) 2001-11-15

Family

ID=22338754

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/029091 Ceased WO2000033778A1 (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)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1656914A1 (fr) 2004-11-10 2006-05-17 Birgit Riesinger Absorbant de non retour pour absorber les exsudats de blessures
US20070053934A1 (en) * 2005-08-26 2007-03-08 Neville Kallenbach Polyvalent multimeric composition containing active polypeptides, pharmaceutical compositions and methods of using the same
EP1450966A4 (fr) * 2001-09-28 2009-09-09 Quick Med Technologies Inc Materiaux absorbants ayant des surfaces polymeres anti-microbiennes non lixiviables a liaison covalente, et procedes de fabrication correspondants
US8007921B2 (en) 2003-02-25 2011-08-30 Quick-Med Technologies, Inc. Gypsum board containing antimicrobial and antibacterial compounds
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

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007024974A2 (fr) * 2005-08-22 2007-03-01 Quick-Med Technologies, Inc. Procede de fixation d'un polyelectrolyte cationique antimicrobien a la surface d'un substrat
JP2016522029A (ja) * 2013-05-17 2016-07-28 シャクティ ニッティング リミテッド 殺菌性複合材料
GB201410510D0 (en) * 2014-06-12 2014-07-30 Fantex Ltd Liquid Antimicrobial

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5035892A (en) * 1988-05-09 1991-07-30 Dow Corning Corporation Antimicrobial superabsorbent compositions and methods

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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
JPH0532722A (ja) * 1991-07-30 1993-02-09 Hymo Corp カチオン性水溶性重合体分散液の製造方法
JP3113348B2 (ja) * 1991-10-31 2000-11-27 株式会社興人 第３級アミノ基含有アクリルポリマーの製造方法
US5981668A (en) * 1996-10-31 1999-11-09 Sanyo Chemical Industries, Ltd. Anti-bacterial water absorbing agent and anti-bacterial water absorbent material
US6146688A (en) * 1997-12-23 2000-11-14 Morgan; Harry C. Method of creating a biostatic agent using interpenetrating network polymers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5035892A (en) * 1988-05-09 1991-07-30 Dow Corning Corporation Antimicrobial superabsorbent compositions and methods

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1156766A4 *

Cited By (8)

* 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
EP1450966A4 (fr) * 2001-09-28 2009-09-09 Quick Med Technologies Inc Materiaux absorbants ayant des surfaces polymeres anti-microbiennes non lixiviables a liaison covalente, et procedes de fabrication correspondants
US8007921B2 (en) 2003-02-25 2011-08-30 Quick-Med Technologies, Inc. Gypsum board containing antimicrobial and antibacterial compounds
EP1656914A1 (fr) 2004-11-10 2006-05-17 Birgit Riesinger Absorbant de non retour pour absorber les exsudats de blessures
US20070053934A1 (en) * 2005-08-26 2007-03-08 Neville Kallenbach Polyvalent multimeric composition containing active polypeptides, pharmaceutical compositions and methods of using the same
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
US11707272B2 (en) 2012-04-06 2023-07-25 Cilag Gmbh International Packaged antimicrobial medical device having improved shelf life and method of preparing same

Also Published As

Publication number Publication date
CN1348346A (zh) 2002-05-08
CA2353436A1 (fr) 2000-06-15
EP1156766A4 (fr) 2005-01-12
KR100689020B1 (ko) 2007-03-09
OA11725A (en) 2005-01-25
AU2169500A (en) 2000-06-26
ID30081A (id) 2001-11-01
CN1183970C (zh) 2005-01-12
EA200100521A1 (ru) 2002-02-28
KR20010105307A (ko) 2001-11-28
MXPA01005773A (es) 2004-04-02
CA2353436C (fr) 2008-01-08
JP2003527145A (ja) 2003-09-16
EP1156766A1 (fr) 2001-11-28
EA004160B1 (ru) 2004-02-26
AU773532B2 (en) 2004-05-27
WO2000033778A9 (fr) 2001-11-15

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