CA2353436C - Intrinsically bactericidal absorbent dressing and method of fabrication - Google Patents
Intrinsically bactericidal absorbent dressing and method of fabrication Download PDFInfo
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- CA2353436C CA2353436C CA002353436A CA2353436A CA2353436C CA 2353436 C CA2353436 C CA 2353436C CA 002353436 A CA002353436 A CA 002353436A CA 2353436 A CA2353436 A CA 2353436A CA 2353436 C CA2353436 C CA 2353436C
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- 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
Abstract
A superabsorbent polymer dressing having antimicrobial properties for use in fabricating wound dressings, sanitary napkins, tampons and the like, includes a synthetic polymer matrix fabricated to have an enhanced surface area. Antimicrobial compounds are coupled to the surface of the polymer matrix by non-siloxane bonds.
Description
Ynains~suY bactcricWal Aosarbeat Drasdog nd biethod of F.ubricatioa Fi~ ef he ++vrs+drnt S Tivs iavontion seriwes ge=ally to absorbeat dressiags, and more Psraculatiy hWy-~sarbent syntiudc polymer drusiags having saamic:obial agents attaobud dereto.
Bscses3al gww in sbsorbent dmmngs for womds, ttaaary in1=ti2mce dispers, and maastruatioa pads can lmd tb sesious me" aanpliatiosws si wdl as sodal diffi=lti=. For exampie, bacmial groa-th in ntiaary inmdsam dlapers or merssavation peds uswlly pt+oduces sanutg, uqpieaaaat odors ttat sra socWUy unooapabls and can cum pexsaos to alter ttuir lifwtyle. Caatveatioaasl abserbcat pads for uritny incootfaoum and meostnurioa am not inbecotttly bweriaidaL Conse~qumtly, tta only way to ivoid g,t+oath of becisda In the zbz orbent drasiags is to ch=aa them at figquent intaWs, evao 3f the -ubsosbant aqmcity of the pad ho not baa nuched. In the am of wound dreuin,p, hwtodmt couUminstipn of acute wonads and fnfiocdoa of cbroaic sicia wounds am msjor cliniaal problkms tdas caa nsnlt ia significant morbidity and, in wvae cs:es, marcaliti-. cAMMeaticcauy, wound d:i;dogs have baea designed to sbsorb wound flui,ds and yos provtde A ma3u eaviroomant tar promoft wound hatina. Iiovvara, such mdst eavuo~ cmts a aueriaau rich remvoir. for bs,ct, " at Srowth in dc d:+asdng. Bsctoda growiag in ttx dtessiaS cm be sbod back into de wound, Wcsaiag the iish of wound iAbactiore, or respmso to toieins, and prvdueiag :t:M, fonl odors.
In aa etfon to addtnss these ptobleou, unn'biodcs or clismial dssmSotnft a=e fre~ueatiy applled topiplly to wewsds priar to corrr.rW the wowd with a drasing.
Alternatively, topical agents are sometimes applied directly to the surface of the dressing. To control foul odors, some known dressings incorporate charcoal powder to absorb molecules generating the foul odor. For some applications, topical application of antibacterial agents is not desirable. For instance, bactericidal agents applied topically to wound dressings have a tendency to seep into the wound being treated. Furthermore, 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 antimircobial 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. In that respect, the disclosed composition provides an improvement over conventional topical treatment systems. However, silanes contain siloxane 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 the silane antimicrobial agent and the underlying polymer. Consequently, antimicrobial agent may seep into a wound and retard wound healing.
The need exists for an improved antimicrobial dressing composition having an antimicrobial agent which can be maintained securely attached to a superabsorbent polymer upon exposure to acids and bases produced by infection and bacterial growth.
In addition to reducing the propensity for detachment of the antimicrobial agent, it would be desirable to provide a surface area enhanced dressing structure for increasing the effectiveness of the antimicrobial agent.
Bscses3al gww in sbsorbent dmmngs for womds, ttaaary in1=ti2mce dispers, and maastruatioa pads can lmd tb sesious me" aanpliatiosws si wdl as sodal diffi=lti=. For exampie, bacmial groa-th in ntiaary inmdsam dlapers or merssavation peds uswlly pt+oduces sanutg, uqpieaaaat odors ttat sra socWUy unooapabls and can cum pexsaos to alter ttuir lifwtyle. Caatveatioaasl abserbcat pads for uritny incootfaoum and meostnurioa am not inbecotttly bweriaidaL Conse~qumtly, tta only way to ivoid g,t+oath of becisda In the zbz orbent drasiags is to ch=aa them at figquent intaWs, evao 3f the -ubsosbant aqmcity of the pad ho not baa nuched. In the am of wound dreuin,p, hwtodmt couUminstipn of acute wonads and fnfiocdoa of cbroaic sicia wounds am msjor cliniaal problkms tdas caa nsnlt ia significant morbidity and, in wvae cs:es, marcaliti-. cAMMeaticcauy, wound d:i;dogs have baea designed to sbsorb wound flui,ds and yos provtde A ma3u eaviroomant tar promoft wound hatina. Iiovvara, such mdst eavuo~ cmts a aueriaau rich remvoir. for bs,ct, " at Srowth in dc d:+asdng. Bsctoda growiag in ttx dtessiaS cm be sbod back into de wound, Wcsaiag the iish of wound iAbactiore, or respmso to toieins, and prvdueiag :t:M, fonl odors.
In aa etfon to addtnss these ptobleou, unn'biodcs or clismial dssmSotnft a=e fre~ueatiy applled topiplly to wewsds priar to corrr.rW the wowd with a drasing.
Alternatively, topical agents are sometimes applied directly to the surface of the dressing. To control foul odors, some known dressings incorporate charcoal powder to absorb molecules generating the foul odor. For some applications, topical application of antibacterial agents is not desirable. For instance, bactericidal agents applied topically to wound dressings have a tendency to seep into the wound being treated. Furthermore, 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 antimircobial 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. In that respect, the disclosed composition provides an improvement over conventional topical treatment systems. However, silanes contain siloxane 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 the silane antimicrobial agent and the underlying polymer. Consequently, antimicrobial agent may seep into a wound and retard wound healing.
The need exists for an improved antimicrobial dressing composition having an antimicrobial agent which can be maintained securely attached to a superabsorbent polymer upon exposure to acids and bases produced by infection and bacterial growth.
In addition to reducing the propensity for detachment of the antimicrobial agent, it would be desirable to provide a surface area enhanced dressing structure for increasing the effectiveness of the antimicrobial agent.
SITMMry ef the ttyentee~
.
It is an object of the presmt invantion to provide an inhereatly b2ctericidal ='.~Fe.~abw.r'',,=t dressing :ta=r:r:g an sr.i=c--1 sutface a.-ci.
S It is aznothca object of the prusent invention to provide an inhereaclv bacter_cida!
superabsorbant dressing having an improved bactericidal attachment strucutre that resiists degiada:~en upon exposure to :ci,ds or bases produced, far instance, during bactezw growth.
Tbeae and other objocts are achievcd by the inh=tly baat,ericldal polymer compoddoa of the premt invendon. In the preferrad embodfinens, the composition comprises a polymer matsix haviti$ 4uaternasy ammoniata groups athered to its surfacx throagh non-siEoxaae bonds. The surfaca araa of the polymer matrix is enhanced, for instance, by electroat;ticsliy apiuniag a 5ber-forming syndade polymer to fozni a&ayed fiber or Slameat.
Altesuqivtly, the PoIY>ver solutior can be wat- or dry-spua to crem a rottgheoed fibet surface by oontioalft the choim of solvent and tbs polyatar salution tdrpe=re. AMtioW
sarface erea mba:,ceQUat is p:onrided by wlming md1=9ar cWns of quemrnary unmoniun pmdatt gwups to dte surhca of the polyme,r mauix. Terbacrnag anay be acoomplished by lanown tiedusiquas wch as Vmfftg and sel4ctive ad:orptiaa.
In an altabue embodimatt of the iavention, non iotuc Momiadal moleotles. Are caouplad to the surlacx of the polymer matdx, in lieu of iontcally-cbarged moWCUles.
Yoaicaily-chuged atdleCules aY+e prau to being neutniized upon ascountering opposiody-cbarged molmdes. Foe instance, positivety.cbarged quammay ammoniuas gz+onps may be steutrailmed by suqptivveiy-dur=ed chloridk ioos psatatt in phydaftiptl tluids. In instances werb such neu~suion is significant enough to reduce die bacbesiadal propesties of tbe exos:iag helow sa aeaeptable level, nen-ioaic suiface groups may be prdesable.
.
It is an object of the presmt invantion to provide an inhereatly b2ctericidal ='.~Fe.~abw.r'',,=t dressing :ta=r:r:g an sr.i=c--1 sutface a.-ci.
S It is aznothca object of the prusent invention to provide an inhereaclv bacter_cida!
superabsorbant dressing having an improved bactericidal attachment strucutre that resiists degiada:~en upon exposure to :ci,ds or bases produced, far instance, during bactezw growth.
Tbeae and other objocts are achievcd by the inh=tly baat,ericldal polymer compoddoa of the premt invendon. In the preferrad embodfinens, the composition comprises a polymer matsix haviti$ 4uaternasy ammoniata groups athered to its surfacx throagh non-siEoxaae bonds. The surfaca araa of the polymer matrix is enhanced, for instance, by electroat;ticsliy apiuniag a 5ber-forming syndade polymer to fozni a&ayed fiber or Slameat.
Altesuqivtly, the PoIY>ver solutior can be wat- or dry-spua to crem a rottgheoed fibet surface by oontioalft the choim of solvent and tbs polyatar salution tdrpe=re. AMtioW
sarface erea mba:,ceQUat is p:onrided by wlming md1=9ar cWns of quemrnary unmoniun pmdatt gwups to dte surhca of the polyme,r mauix. Terbacrnag anay be acoomplished by lanown tiedusiquas wch as Vmfftg and sel4ctive ad:orptiaa.
In an altabue embodimatt of the iavention, non iotuc Momiadal moleotles. Are caouplad to the surlacx of the polymer matdx, in lieu of iontcally-cbarged moWCUles.
Yoaicaily-chuged atdleCules aY+e prau to being neutniized upon ascountering opposiody-cbarged molmdes. Foe instance, positivety.cbarged quammay ammoniuas gz+onps may be steutrailmed by suqptivveiy-dur=ed chloridk ioos psatatt in phydaftiptl tluids. In instances werb such neu~suion is significant enough to reduce die bacbesiadal propesties of tbe exos:iag helow sa aeaeptable level, nen-ioaic suiface groups may be prdesable.
rimmilcd b A novel antibacternipolymer oomposition is fabriamd to have an enhaaced wrcacc arM sad superabsozbent capacity for biologicil fluids, iaclndiag arine, blood, and wound eC::c.
S In the prefcrred cmSodiment of dw present ir,vention, dw composition iaclvdzs a polymer matrix having quamuary amrnoniam compauoda atrchcd to the surlace of dw polymer matrfx. Thc polymer mamix is comprised of a plur4ity of hydrephaic fibars or &]aznesYts which can be fabrfcated in any suitable manner. For examplc, :uitable fibers or filamants aan be fabrioated by wet- or dry-spinning a fYber-formiag synmt!wtic polymcr from a spmning soivmt. Tise resulting polymer has svperabsaabent cxpacity. GeoeaIly, poiymecs c.apable of absoacDing from about thircy co sixry grrmi of wataa per gram of polymer ub caosidand oo be wpmabsorbent. kAMplea of auperabsaabcnt polymrss wb3cb can be fabriptu+d iti this maaAaz mr,iude polyacrylic wids+ IolyethYloo oacSdes ared potyvi,nyl atcohols. For "ample, mstbods for spinning polyetl-Ykae oxide using loetooe solvwt aro wttllrnow+n.
Sigalficantly, do pWYuw matrix is fabricabod to bave an eQEianced rafae =VL
Enhaoc.itig the surtue uea of tfie polymer manix s+ewlts in impmed aluorptiaa of bielogicsl tluids, snd ieanmses dw avafilability of sites for amchment of the sntiiaicmbial qeiaaernsury ammanium eomapouads. A cornspondi:tg ia=usa in the qmrttiry and Qensiry of antlsaiarobial siua, in turn, a>ianm the efflday of the composidca in ]dlling oWnisnns such as bactesia and viruses.
It may o=tr m one sldaled in the art of polyjm sCieace tl>at a vatlay of inerbods are avaflable for accomposhing wriitse am moQfiicadon. Pfetessbly, arface uat enbancment is aocomplishod by a modifled spinning or cuttag memod. For iAstaoce, electrosUdc sp~.~ning is a eroWfed spinaimg teahnique which results in lmying of the Sbw as it Wts the spineretre.
AUM=dVely, a poly= sdntton caa be wet or dry-spun to craats s rougbeaod fiber sur"
by coutroliing tha solve,ut typs and the polymer solution M%M=re. This aechnology is weU
]caown and has been appifed, for exatnple, ia the manubcxute of asymmecic membranes haviag rotlghened pores for dialysis. ?he siae of thn mugheaad pores is pzfmauily cmbroll,ed 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 enhanced by tethering chains of antimicrobial groups to the outer surface of the individual polymer fibers.
Preferably, molecular chains of quaternary ammonium pendent groups are fabricated to have at least one end adapted for attachment to a fiber surface. For instance, surface grafting may be accomplished by creating surface free radicals as initiation sites from peroxide generation (ozone or microwave). Alternatively, surface attachment of an interpenetrating 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. In particular, the tethered antimicrobial chains extend into the particular biological solution to bind to harmful bacterial and viral organisms. In contrast to known dressing compositions in which a monolayer (or near monolayer) of bactericidal compound is directly attached to a fiber surface, 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. Preferably, 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 trimethylammonium ethyl methacrylate to graft polymerized to a modified polyethylene surface is described by Yahaioui (Master's Thesis, University of Florida, 1986). Yahaioui 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 copolymers can also be used.
In contrast to known compositions in which an antimicrobial structure is achieved by covalently bonding silane groups to the surface of the base polymer, the present invention incorporates a chemical structure which is based on polymerization (i.e., surface grafting) of monomers containing all carbon-carbon, carbon-oxygen and carbon-nitrogen main bonds, such as the dialkyl, 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 applied to a wound dressing, such degradation could result in antimicrobial agents detaching from the polymer matrix and entering a wound site. In some cases, this can have the deleterious effect of retarding wound healing.
In an alternate embodiment of the present invention, anionic antibactericidal groups are immobilized on the surface of a superabsorbant dressing to improve the antibactericidal efficacy of the dressing. The positive charge associated with quaternary ammonium groups, for example, can be neutralized by negative ions, such as chloride ions present in physiological fluids such as urine and plasma. For applications where the degree of neutralization will significantly reduce the effectiveness of the antibactericidal agent, 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 TritonTM-100, TweenTM 20 and deoxycholate. For instance, 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 surfactant.
Dimethyldiallyl ammonium chloride is one example of a suitable monomer which may be used with the present invention. This monomer, commonly referred to as DMDAC 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 hydrolytic 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.
While the preferred embodiments of the invention have been illustrated and described, it will be clear that the invention is not so limited. Numerous modifications, changes, vaziad,oas, mbsdmr>ans VA equEv.iats wilt cwur to thoae skilled in the art withauc depar6n8 fTCDI ttbE si7tlZt aC1d 9COpC of the PrCSmt iAYlSLiCn a4 df.SQ'l'3bM in 1M
cWI!!s.
S In the prefcrred cmSodiment of dw present ir,vention, dw composition iaclvdzs a polymer matrix having quamuary amrnoniam compauoda atrchcd to the surlace of dw polymer matrfx. Thc polymer mamix is comprised of a plur4ity of hydrephaic fibars or &]aznesYts which can be fabrfcated in any suitable manner. For examplc, :uitable fibers or filamants aan be fabrioated by wet- or dry-spinning a fYber-formiag synmt!wtic polymcr from a spmning soivmt. Tise resulting polymer has svperabsaabent cxpacity. GeoeaIly, poiymecs c.apable of absoacDing from about thircy co sixry grrmi of wataa per gram of polymer ub caosidand oo be wpmabsorbent. kAMplea of auperabsaabcnt polymrss wb3cb can be fabriptu+d iti this maaAaz mr,iude polyacrylic wids+ IolyethYloo oacSdes ared potyvi,nyl atcohols. For "ample, mstbods for spinning polyetl-Ykae oxide using loetooe solvwt aro wttllrnow+n.
Sigalficantly, do pWYuw matrix is fabricabod to bave an eQEianced rafae =VL
Enhaoc.itig the surtue uea of tfie polymer manix s+ewlts in impmed aluorptiaa of bielogicsl tluids, snd ieanmses dw avafilability of sites for amchment of the sntiiaicmbial qeiaaernsury ammanium eomapouads. A cornspondi:tg ia=usa in the qmrttiry and Qensiry of antlsaiarobial siua, in turn, a>ianm the efflday of the composidca in ]dlling oWnisnns such as bactesia and viruses.
It may o=tr m one sldaled in the art of polyjm sCieace tl>at a vatlay of inerbods are avaflable for accomposhing wriitse am moQfiicadon. Pfetessbly, arface uat enbancment is aocomplishod by a modifled spinning or cuttag memod. For iAstaoce, electrosUdc sp~.~ning is a eroWfed spinaimg teahnique which results in lmying of the Sbw as it Wts the spineretre.
AUM=dVely, a poly= sdntton caa be wet or dry-spun to craats s rougbeaod fiber sur"
by coutroliing tha solve,ut typs and the polymer solution M%M=re. This aechnology is weU
]caown and has been appifed, for exatnple, ia the manubcxute of asymmecic membranes haviag rotlghened pores for dialysis. ?he siae of thn mugheaad pores is pzfmauily cmbroll,ed 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 enhanced by tethering chains of antimicrobial groups to the outer surface of the individual polymer fibers.
Preferably, molecular chains of quaternary ammonium pendent groups are fabricated to have at least one end adapted for attachment to a fiber surface. For instance, surface grafting may be accomplished by creating surface free radicals as initiation sites from peroxide generation (ozone or microwave). Alternatively, surface attachment of an interpenetrating 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. In particular, the tethered antimicrobial chains extend into the particular biological solution to bind to harmful bacterial and viral organisms. In contrast to known dressing compositions in which a monolayer (or near monolayer) of bactericidal compound is directly attached to a fiber surface, 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. Preferably, 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 trimethylammonium ethyl methacrylate to graft polymerized to a modified polyethylene surface is described by Yahaioui (Master's Thesis, University of Florida, 1986). Yahaioui 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 copolymers can also be used.
In contrast to known compositions in which an antimicrobial structure is achieved by covalently bonding silane groups to the surface of the base polymer, the present invention incorporates a chemical structure which is based on polymerization (i.e., surface grafting) of monomers containing all carbon-carbon, carbon-oxygen and carbon-nitrogen main bonds, such as the dialkyl, 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 applied to a wound dressing, such degradation could result in antimicrobial agents detaching from the polymer matrix and entering a wound site. In some cases, this can have the deleterious effect of retarding wound healing.
In an alternate embodiment of the present invention, anionic antibactericidal groups are immobilized on the surface of a superabsorbant dressing to improve the antibactericidal efficacy of the dressing. The positive charge associated with quaternary ammonium groups, for example, can be neutralized by negative ions, such as chloride ions present in physiological fluids such as urine and plasma. For applications where the degree of neutralization will significantly reduce the effectiveness of the antibactericidal agent, 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 TritonTM-100, TweenTM 20 and deoxycholate. For instance, 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 surfactant.
Dimethyldiallyl ammonium chloride is one example of a suitable monomer which may be used with the present invention. This monomer, commonly referred to as DMDAC 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 hydrolytic 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.
While the preferred embodiments of the invention have been illustrated and described, it will be clear that the invention is not so limited. Numerous modifications, changes, vaziad,oas, mbsdmr>ans VA equEv.iats wilt cwur to thoae skilled in the art withauc depar6n8 fTCDI ttbE si7tlZt aC1d 9COpC of the PrCSmt iAYlSLiCn a4 df.SQ'l'3bM in 1M
cWI!!s.
Claims (13)
1. ~An intrinsically antimicrobial material comprising:
an absorbent polymeric matrix having an enhanced surface area;
wherein said enhanced surface area further comprises a polymer of antimicrobial monomeric moieties attached to said matrix via non-siloxane covalent chemical bonds so as to result in a structure which is less prone to degradation by acids or bases produced during bacterial growth and consequent detachment of said polymer of antimicrobial monomeric moieties from the matrix, whereby the material remains antimicrobial after exposure of the material to skin or aqueous biological fluids.
an absorbent polymeric matrix having an enhanced surface area;
wherein said enhanced surface area further comprises a polymer of antimicrobial monomeric moieties attached to said matrix via non-siloxane covalent chemical bonds so as to result in a structure which is less prone to degradation by acids or bases produced during bacterial growth and consequent detachment of said polymer of antimicrobial monomeric moieties from the matrix, whereby the material remains antimicrobial after exposure of the material to skin or aqueous biological fluids.
2. ~The material of claim 1, wherein said aqueous biological fluids are bodily fluids, sweat, tears, mucus, urine, menses, blood, wound exudates, or mixtures thereof.
3. ~The material of claim 1, wherein molecules of said polymer are attached to said matrix via one or more covalent carbon-oxygen-carbon bonds, or carbon-carbon bonds, or carbon-nitrogen bonds, or combinations thereof.
4. ~The material of claim 1, wherein said antimicrobial monomeric moieties are allyl- or vinyl-containing monomers.
5. ~The material of claim 1, wherein said antimicrobial monomeric moieties comprise at least one quaternary ammonium compound.
6. ~The material of claim 5, wherein the quaternary ammonium compound is dimethyldiallyl ammonium chloride, or a trialkyl(p-vinylbenzyl)ammonium chloride, or a p-trialkylaminoethyl styrene monomer.
7. ~The material of claim 1, wherein said matrix comprises cellulose.
8. The material of claim 1, wherein said matrix comprises a polyethylene oxide, a polyvinyl alcohol, or a polyacrylate.
9. The material of claim 1, wherein said matrix consists essentially of hydrophilic fibers or filaments having a superabsorbent capacity for aqueous biological fluids as evidenced by being capable of absorbing at least about thirty times its own weight of water.
10. An absorbent dressing, diaper, sanitary pad, or tampon comprising the intrinsically antimicrobial material of claim 1.
11. A method for fabricating the intrinsically antimicrobial material of claim comprising the steps of:
forming an absorbent polymeric matrix having an enhanced surface area; and attaching a polymer of antimicrobial monomeric moieties in an amount sufficient to impart to the material an antimicrobial effect which remains after exposure of the material to skin or aqueous biological fluids.
forming an absorbent polymeric matrix having an enhanced surface area; and attaching a polymer of antimicrobial monomeric moieties in an amount sufficient to impart to the material an antimicrobial effect which remains after exposure of the material to skin or aqueous biological fluids.
12. The method of claim 11, wherein said antimicrobial monomeric moieties comprise at least one quaternary ammonium compound.
13. The method of claim 12, wherein the quaternary ammonium compound is dimethyldiallyl ammonium chloride, or a trialkyl(p-vinylbenzyl)ammonium chloride, or a p-trialkylaminoethyl styrene monomer.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US11147298P | 1998-12-08 | 1998-12-08 | |
| US60/111,472 | 1998-12-08 | ||
| PCT/US1999/029091 WO2000033778A1 (en) | 1998-12-08 | 1999-12-08 | Intrinsically bactericidal absorbent dressing and method of fabrication |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2353436A1 CA2353436A1 (en) | 2000-06-15 |
| CA2353436C true CA2353436C (en) | 2008-01-08 |
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|---|---|---|---|
| CA002353436A Expired - Fee Related CA2353436C (en) | 1998-12-08 | 1999-12-08 | Intrinsically bactericidal absorbent dressing and method of fabrication |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1156766A4 (en) |
| JP (1) | JP2003527145A (en) |
| KR (1) | KR100689020B1 (en) |
| CN (1) | CN1183970C (en) |
| AU (1) | AU773532B2 (en) |
| CA (1) | CA2353436C (en) |
| EA (1) | EA004160B1 (en) |
| ID (1) | ID30081A (en) |
| MX (1) | MXPA01005773A (en) |
| OA (1) | OA11725A (en) |
| WO (1) | WO2000033778A1 (en) |
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| 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 (en) | 2003-02-25 | 2004-09-10 | Quick-Med Technologies, Inc. | Improved antifungal gypsum board |
| DE202004017465U1 (en) | 2004-11-10 | 2005-12-15 | Riesinger, Birgit | Disposable absorbent body for connection to the skin and mucosal surfaces of the human body |
| CA2620203C (en) * | 2005-08-22 | 2013-11-05 | Quick-Med Technologies Inc. | Method of attaching an antimicrobial cationic polyelectrolyte to the surface of a substrate |
| WO2007025178A2 (en) * | 2005-08-26 | 2007-03-01 | New York University | Rolyvalent multimeric compositions containing active polypeptides, pharmaceutical compositions and methods of using the same |
| WO2012065610A1 (en) | 2010-11-18 | 2012-05-24 | Vestergaard Frandsen Sa | Method and substrate with a quat coating |
| US10245025B2 (en) * | 2012-04-06 | 2019-04-02 | Ethicon, Inc. | Packaged antimicrobial medical device having improved shelf life and method of preparing same |
| WO2014184640A1 (en) * | 2013-05-17 | 2014-11-20 | Shakthi Knitting Limited | Microbicidal composite material |
| GB201410510D0 (en) * | 2014-06-12 | 2014-07-30 | Fantex Ltd | Liquid Antimicrobial |
Family Cites Families (8)
| 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 |
| JPH0532722A (en) * | 1991-07-30 | 1993-02-09 | Hymo Corp | Production of cationic water-soluble polymer dispersion |
| JP3113348B2 (en) * | 1991-10-31 | 2000-11-27 | 株式会社興人 | Method for producing tertiary amino group-containing acrylic polymer |
| 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 |
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1999
- 1999-12-08 WO PCT/US1999/029091 patent/WO2000033778A1/en active IP Right Grant
- 1999-12-08 CA CA002353436A patent/CA2353436C/en not_active Expired - Fee Related
- 1999-12-08 ID IDW00200101469A patent/ID30081A/en unknown
- 1999-12-08 MX MXPA01005773A patent/MXPA01005773A/en not_active IP Right Cessation
- 1999-12-08 AU AU21695/00A patent/AU773532B2/en not_active Ceased
- 1999-12-08 OA OA1200100142A patent/OA11725A/en unknown
- 1999-12-08 CN CNB998142298A patent/CN1183970C/en not_active Expired - Fee Related
- 1999-12-08 EA EA200100521A patent/EA004160B1/en not_active IP Right Cessation
- 1999-12-08 EP EP99966054A patent/EP1156766A4/en not_active Withdrawn
- 1999-12-08 KR KR1020017007093A patent/KR100689020B1/en not_active IP Right Cessation
- 1999-12-08 JP JP2000586273A patent/JP2003527145A/en active Pending
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| AU773532B2 (en) | 2004-05-27 |
| CN1183970C (en) | 2005-01-12 |
| EP1156766A1 (en) | 2001-11-28 |
| WO2000033778A1 (en) | 2000-06-15 |
| EA004160B1 (en) | 2004-02-26 |
| JP2003527145A (en) | 2003-09-16 |
| ID30081A (en) | 2001-11-01 |
| CA2353436A1 (en) | 2000-06-15 |
| KR20010105307A (en) | 2001-11-28 |
| CN1348346A (en) | 2002-05-08 |
| WO2000033778A9 (en) | 2001-11-15 |
| AU2169500A (en) | 2000-06-26 |
| OA11725A (en) | 2005-01-25 |
| MXPA01005773A (en) | 2004-04-02 |
| EP1156766A4 (en) | 2005-01-12 |
| KR100689020B1 (en) | 2007-03-09 |
| EA200100521A1 (en) | 2002-02-28 |
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| MKLA | Lapsed |
Effective date: 20141208 |