Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
  • A01N37/46—N-acyl derivatives
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof

Definitions

• microorganisms can be present on surfaces in hospitals, nursing homes, schools, restaurants, grocery stores, kitchens, bathrooms, gyms, etc. as well as in liquids such as drinking water,
• One approach for killing and/or removing these microorganisms is by using solutions containing detergents, biocides, antibiotics, or other chemicals. These solutions may also be impregnated into fibrous webs, such as wipes and nonwovens, for delivery to a contaminated surface or for filtration.
• these substances can be successful in killing or removing the microorganisms, exposure to these chemicals can be harmful, Further, increased use can lead to the microorganisms having increased resistance to such chemicals. Additionally, over time, the use of such chemicals can corrode or damage the surfaces to which they are applied.
• webs for capturing and trapping negatively charged bacteria are generally limited to the application of metal cation solutions such as aluminum cations to the surface of a web.
• metal cation solutions such as aluminum cations
• these methods only utilize the cation ic functionalities to interact with the negatively charged bacteria
• the metal cations are capable of leaching from the web and contaminating the surface and/or liquid that is in contact with the web.
• a fibrous web for use in removing bacteria wherein the web comprises a cationic polymer.
• the cationic polymer has an affinity for the negatively charged cell wails of bacteria.
• the cationic polymer comprises a cationic monomer and a hydrophobic monomer, The molar ratio of the cationic monomer to the hydrophobic monomer is greater than about 1 :1 ,
• a method for removing bacteria from a surface or a liquid comprises contacting the surface or the liquid with a fibrous web comprising a cationic polymer.
• the cationic polymer has an affinity for the negatively charged ceil walls of bacteria.
• the cationic polymer comprises a cationic monomer and a hydrophobic monomer, The molar ratio of the cationic monomer to the hydrophobic monomer is greater than about 1 :1.
• Alkyi refers to monovalent saturated aliphatic hydrocarbyl groups having from 1 to 10 carbon atoms and, in some embodiments, from 1 to 5 carbon atoms.
• C x . y aiky refers to alkyi groups having from x to y carbon atoms.
• This term includes, by way of example, linear and branched hydrocarbyl groups such as methyl (CH 3 ), ethyl (CH3CH2), ⁇ -propyl (CH3CH2CH2), isopropyl ((Ch ⁇ CH), n-butyl ⁇ CH3CH2CH2CH2 ⁇ , isobutyi ((CH 3 )2CHCH 2 ), sec-butyl ((ChbXCHsCH ⁇ CH), f-butyl (iCH ⁇ C), n-pentyl (CH3CH2CH2CH2CH2), and neopentyi ((CH CCte).
• linear and branched hydrocarbyl groups such as methyl (CH 3 ), ethyl (CH3CH2), ⁇ -propyl (CH3CH2CH2), isopropyl ((Ch ⁇ CH), n-butyl ⁇ CH3CH2CH2CH2 ⁇ , isobutyi ((CH 3 )2CHCH 2 ),
• (C x -C y ) aikenyl refers to aikenyl groups having from x to y carbon atoms and is meant to include for example, ethenyi, propenyi, 1 ,3-butadienyl, and so forth.
• Aryl refers to an aromatic group of from 3 to 14 carbon atoms and no ring heteroatoms and having a single ring (e.g., phenyl) or multiple condensed (fused) rings (e.g., naphthy! or anthryl).
• a single ring e.g., phenyl
• multiple condensed (fused) rings e.g., naphthy! or anthryl.
• the term “Aryl” applies when the point of attachment is at an aromatic carbon atom (e.g., 5,6,7,8 tetrahydronaphtha!ene-2-y! is an aryl group as its point of attachment is at the 2-position of the aromatic phenyl ring).
• Heteroaryi refers to an aromatic group of from 1 to 14 carbon atoms and 1 to 8 heteroatoms selected from oxygen, nitrogen, and sulfur and includes single ring (e.g. imidazolyl) and multiple ring systems (e.g. benzimidazol-2-yl and benzimidazol-6-yl).
• single ring e.g. imidazolyl
• multiple ring systems e.g. benzimidazol-2-yl and benzimidazol-6-yl.
• the term “heteroaryl” applies if there is at least one ring heteroafom and the point of attachment is at an atom of an aromatic ring (e.g. 1,2,3,4-tetrahydrcquino!in-6-y!
• the nitrogen and/or the sulfur ring atom(s) of the heteroaryl group are optionally oxidized to provide for the N oxide (N- ⁇ 0), sulfinyi, or suifonyi moieties.
• heteroaryl groups include, but are not limited to, pyridyi, furanyl, thienyl, thiazoiyl, isothiazolyl, triazolyl, imidazoiyl, imidazoline, isoxazoiyl, pyrroiyl, pyrazolyi, pyridazinyl, pyrimidinyi, purinyl, phthalazyi, naphthylpryidyi, benzofuranyl, tetrahydrobenzofuranyl, isobenzofuranyl, benzothiazolyl, benzoisothiazolyl, benzotriazoiyS, indolyl, isoindolyi, indolizinyi, dihydroindoiyl, indazolyi, indolinyi, benzoxazolyl, quinoiyl, isoquinolyi, quinolizyl, quianazoSyl, quirsoxaiyl,
• benzisoxazolyi benzothienyl, benzopyridazinyi, pteridinyl, carbazolyl, carbolinyl, phenanthridinyl, acridinyl, phenanthrolinyi, phenazinyl, phenoxazinyl, phenothiazinyi, and phthalimidyl.
• Heterocyclic or “heterocycle” or “h ete rocyc toa Ik or “heterocyclyl” refers to a saturated or partially saturated cyclic group having from 1 to 14 carbon atoms and from 1 to 8 heteroatoms selected from nitrogen, sulfur, or oxygen and includes single ring and multiple ring systems including fused, bridged, and spiro ring systems.
• heterocyclic For multiple ring systems having aromatic and/or non-aromatic rings, the terms “heterocyclic”, “heierocycle”, “heierocycioalky!, or “heterocyclyi” apply when there is at least one ring heteroatom and the point of attachment is at an atom of a non-aromatic ring (e.g.
• heterocyclyl groups include, but are not limited to, azetidinyi, tetrahydropyranyl, piperidinyi, N- methyipiperidin-3-yi, piperazinyl, N-methylpyrrolidin-3-yl, 3-pyrrolidinyi, 2-pyrrolidon-l-yi, morpholinyl, thiomorpholinyi, imidazolidinyi, and pyrrolidinyl.
• an aryl, heteroaryl, or heterocyclyi group may be substituted with from 1 to 8, in some embodiments from 1 to 5, in some embodiments from 1 to 3, and in some embodiments, from 1 to 2 substituents selected from alkyi, aikenyi, alkynyi, alkoxy, acyi, acyiamino, acyioxy, amino, quaternary amino, amide, imino, amidino, aminocarbony!amino, amidinocarbonylamino, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonyiamino, aminocarbonyioxy, aminosuifonyS, aminosu!fonyloxy, aminosuifonylamino, aryl, aryioxy, arylthio, azido, carboxyi, carboxyl
• the present invention is directed to a fibrous web containing a plurality of fibers wherein the web also includes a cationic polymer.
• the cationic polymer is synthesized from a cationic monomer containing a cationic functional group that has an affinity for the negatively charged ceil walls of microorganisms, such as bacteria.
• the ability of the polymer to attract and retain these microorganisms may be further enhanced by also incorporating a hydrophobic monomer.
• the hydrophobic functional groups present within the monomer may interact with the hydrophobic groups that are present in the cell wails of these microorganisms.
• the functional groups may also be capable of interacting, such as chemically, electrostatically, or physically, with the fibers of the fibrous web thereby immobilizing the polymer onto or within the web.
• the cationic functional groups may interact with functional groups, such as hydroxy! groups, on the fibers, such as cellulose fibers, within a fibrous web.
• the hydrophobic functional groups and polymer backbone may interact the other polymeric based materials and synthetic polymers, if any, incorporated within the web. As such, the polymer can become integral and become embedded into the web thereby inhibiting removal or transfer to another liquid, surface, or surrounding environment.
• the present inventors have also discovered that these interactions can be optimized when utilizing the cationic monomer and the hydrophobic monomer in a specific ratio.
• the cationic polymer has a net positive charge wherein the molar ratio of the cationic monomer to the hydrophobic monomer is about 1:1 or more, and in another embodiment about 1.5:1 or more, and in a particular embodiment about 2:1 or more to about 15:1 or less, and in another embodiment about 10:1 or less, and in a particular embodiment about 5:1 or less such as at about 3:1.
• the present inventors have discovered that such molar ratio provides a cationic polymer that is capable of effectively interacting with bacteria while also remaining immobilized due to the interactions with the fibers of the fibrous web.
• Gram positive bacteria for example, contain teichoic acids that give the ceil wail an overall negative charge due to the presence of phosphodiester bonds between teichoic acid monomers.
• Gram negative bacteria on the other hand, contain highly charged lipopoiysaccharides that may confer an overall negative charge to the cell wail, Regardless, the present inventors have discovered that utilizing a cationic poiymer having cationic functional groups and hydrophobic functional groups in a specified ratio optimally enhances the ability of the polymer and web to capture and retain certain microorganisms, such as bacteria, thereby removing them from a surface or liquid and also inhibiting their spread.
• the poiymer may help protect against the spread or infection of pathogens without the use of chemicals, such as antiseptics or antibiotics.
• the cationic polymer is employed in the present invention for interacting with the negatively charged well calls of microorganisms. These interactions allow the poiymer to attract and retain negatively charged matter, such as molecules, particles, microbes, ceils, fungi, anions, bacteria, other microorganisms, pathogens, and the like, through the application of physical means and Coulombic attraction, without the use of harsh chemicals such as some antimicrobials. As such, the cationic poiymer prevents the transfer of bacteria through a fibrous web and prevents the spread of bacteria among surfaces and liquids that may contact the fibrous web,
• the cationic polymer may have the general structure as identified in Formula I;
• A denotes a cationic monomer
• p is the number of units of monomer A and is greater than 1 , such as from about 2 to about
• 2000 such as from about 2 to about 1000;
• q is the number of units of monomer B and is greater than 1 , such as from about 2 to about
• 2000 such as from about 2 to about 1000.
• the cationic polymer contains a first monomer A and a second monomer B
• Monomer A may be a cationic monomer and monomer B may be a hydrophobic monomer.
• Cationic monomer A may contain a cationic functional group while hydrophobic monomer B may contain a hydrophobic functional group,
• cationic functional groups are those that have a net positive charge, The presence of this charge is generally dictated by the pH of the environment in which the group is found.
• the groups are represented as charged functional groups generally at a physiological pH of 7,4, Without intending to be limited by theory, it is believed that the affinity of the cationic polymer for the negatively charged walls of microorganisms, such as bacteria, is generally due to the presence of these cationic functional groups that can electrostatically bind to the cell walls,
• hydrophobic functional groups are groups without electronegative atoms thus preventing the ability to form a hydrogen bond with aqueous solvents, if hydrophobic, a molecule or part of a molecule will actively repel or exclude water. Without intending to be limited by theory, it is believed that the hydrophobic functional groups are also capable of interacting with the hydrophobic groups that are present in the cell walls of the microorganisms, such as bacteria.
• the functional groups may also be capable of interacting, such as chemically, electrostatically, or physically, with the fibers of the fibrous web thereby immobilizing the polymer onto or within the web, As such, the polymer can become integral and become embedded into the web thereby inhibiting removal or transfer to another liquid, surface, or surrounding environment.
• the cationic functional groups may interact wiih functional groups, such as hydroxy! groups, on the fibers, such as cellulose fibers, within a fibrous web.
• the hydrophobic functional groups and polymer backbone may interact the other polymeric based materials and synthetic polymers, if any, Incorporated within the web.
• the cationic polymer not only provides a surface of fixed functional groups for capturing and retaining bacteria but also provides functional groups for interacting with the fibers of the fibrous web,
• p denotes the number of monomer units of monomer A present in the cationic polymer while q denotes the number of monomer units of monomer B present in the cationic polymer.
• p and q are greater than 1 , such as from about 2 to about 2000, and in another embodiment from about 2 to about 1000.
• the cationic monomer A is present in the polymer in an amount greater than the hydrophobic monomer B.
• the molar ratio (p:q) of the cationic monomer to the hydrophobic monomer is about 1 : 1 or more, and in another embodiment about 1.5: 1 or more, and in a particular embodiment about 2:1 or more to about 15:1 or less, and in another embodiment about 10:1 or less, and in a particular embodiment about 5:1 or less.
• the cationic polymer may have a molecular weight of about 10,000 g/moS or more, and in another embodiment about 25,000 g/mol or more to about 500,000 g/moi or less, and in another embodiment about 300,000 g/moi or less.
• the polymer is a water-soluble polymer having a molecular weight of from about 100,000 g/moi to about 200,000 g/moi.
• water-soluble refers to materials ⁇ bich dissolve in water at 37° C. to give a true solution as opposed to materials which form a latex or suspension of undissolved particles,
• the respective cationic monomer and hydrophobic monomers may be any monomers known in the art.
• monomer may be an acrylamide monomer.
• an acrylamide monomer may constitute an acrylamide, a methacryiamide, a derivative thereof, or a combination thereof
• the respective monomer may be an acryiate monomer or an acryiate ester monomer
• an acryiate monomer or acryiate ester monomer may be produced from acrylic acid or an acryiate, methacryltc acid or a methacry!ate, a derivative thereof, or a combination thereof.
• the polymer empioyed is a non-crossiinking polymer such that the rheo!ogy of the polymer system in solution is substantially retained and does not require further processing steps.
• the monomers may be produced using any method known in the art.
• the monomers may be synthesized with a first constituent and a second constituent
• the first constituent may be an acryiate monomer produced from an acrylic acid or an acryiate, a methacrylic acid or a methacrylate, a derivative thereof, or a combination thereof.
• the second constituent may be a compound containing the cationic functional group or hydrophobic functional group.
• the carboxyl group of the first constituent may be reacted with the second constituent to form a carboxylic ester
• the carboxyl group of the first constituent may be reacted with an amine group of the second constituent to form an amide.
• any esterification reaction and/or amide synthesis known in the art may be utilized to produce the monomers for synthesis of the polymers.
• the raw materials utilized to produce the monomers are commercially available from Sigma and whereby the monomers can be commercially synthesized by Lumigenix,
• the second constituent may be any compound that is capable of providing the cationic functional group or hydrophobic functional group, as mentioned above, to the respective monomer.
• the second constituent may be an amino acid, such as a natural amino acid.
• the amino acid may contain the desired cationic functional group or hydrophobic functional group.
• the second constituent may be arginine, lysine, hisfidine, alanine, valine, isoleucine, leucine, methionine, phenylalanine, tyrosine, and/or tryptophan.
• the second constituent may be arginine, lysine, histidine, or a combination thereof.
• the second constituent for the cationic monomer is lysine.
• the second constituent may be alanine, valine, isoleucine, leucine, methionine, phenylalanine, tyrosine, tryptophan, or a combination thereof, in one particular embodiment, the second constituent for the hydrophobic monomer is phenylalanine.
• cationic functional group and the hydrophobic functional group may be contained within their respective monomers such that they are capable of interacting with
• the cationic functional group, hydrophobic functional group, or both may be present within the polymer backbone, in another embodiment, the cationic functional group, hydrophobic functional group, or both may be present as pendant functional groups attached to the backbone of the cationic polymer, In such embodiments, the pendant functional groups are extended or branched from the polymer backbone.
• Formula II depicts a structure wherein the functional groups are present as pendant groups:
• R1 and R2 are each independently hydrogen, a C1-C aikyl group, or a C1-C 4 alkenyl group;
• R3 and R4 are each independently hydrogen, a hydroxy! group, a C1-C 4 aikyl group, or a C1-C 4 alkenyl group;
• R5 is an organic substituent containing a cationic functional group
• R8 is an organic substituent containing a hydrophobic functional group
• p is the number of units of monomer A and is greater than 1 , such as from about 2 to about 2000, such as from about 2 to about 1000
• q is the number of units of monomer B and is greater than 1 , such as from about 2 to about 2000, such as from about 2 to about 1000;
• n, v, and w are each independently from 0 to 5, such as 0, 1, or 2.
• R1 and R2 are the terminal end groups of the cationic polymer
• R1 and R2 may each independently be hydrogen, a C1-C4 alkyl group, or a C1-C4 alkenyl group
• R1 , R2, or both are a C1-C4 aikyl group, such as a methyl, ethyl, propyl, or butyl group.
• R1 , R2, or both are a C1-C2 alkyl group, In a particular embodiment, R1 , R2, or both are a methyl group.
• R3 and R4 are pendant groups that branch from the polymer backbone, R3 and R4 may each independently be hydrogen, a hydroxy! group, a C1-C4 alkyl group, or a C1-C4 alkenyl group.
• R.3, R4, or both are a C1-C4 alkyl group, such as a methyl, ethyl, propyl, or butyl group, in one embodiment, R3.
• R4, or both are a C1-C2 alkyl group.
• R3, R4, or both are a methyl group
• p and q are defined the same as with respect to the description of Formula I provided above. For instance, p and q are greater than 1 , such as from about 2 to about 2000, and in another embodiment from about 2 to about 1000. Additionally, the molar ratio (p:q) of the cationic monomer to the hydrophobic monomer is about 1 :1 or more, and in another embodiment about 1 ,5:1 or more, and in a particular embodiment about 2:1 or more to about 15:1 or less, and in another embodiment about 10:1 or less, and in a particular embodiment about 5:1 or less.
• R5 is an organic substituent containing a cationic functional group and R6 is an organic substituent containing a hydrophobic functional group.
• the formulae for R5 and R6 may have the general structures as identified in Formula ill and Formula IV, respectively:
• Formula 111 Formula IV wherein: X and Y are each independently an amide (-C(O)NH- or -NHC(0 ⁇ - ⁇ or a carboxylic ester (- C(0)0- or -OC ⁇ 0)- ⁇ ;
• R7 is a direct bond between the C and R8, a Ci-C 5 alkyi group, or a C1-C 5 alkeny! group;
• R8 is an amino group having the structure -N(R13) ⁇ R1 ), an ammonium group having the structure -N ⁇ R15)(R16) ⁇ R17), a N containing heteroary! group, or a N containing heterocyciyl group;
• R9 and R10 are each independently hydrogen, a C1-C10 aikyl group, or a C1-C10 aikenyi group;
• R11 is a direct bond between the C and R12, a C1-C 5 aikyl group, or a C1-C 5 aikenyi group;
• R12 is a C -C 20 aikyf group, a C2-C 20 aiky!ene group, an aryl group, or a heteroary! group;
• R13 and R14 are each independently hydrogen, a C1-C 5 aikyl group, a Ci-C 5 aikenyi group, or -C(NR18)N(R19)(R20);
• R15, R16, and R17 are each independently hydrogen, a Ci-C 5 aikyl group, a C1-C 5 aikenyi group, or -C(NR18)N(R19) ⁇ R20), wherein at least one of R15, R16, or R17 is hydrogen; and
• R18, R19, and R20 are each independently hydrogen, a C1-C 5 aikyl group, or a Ci-C 5 aikenyi group.
• the cationic functional group may be contained within R8,
• R8 may be an amino group having the structure -N(R13) ⁇ R14), an ammonium group having the structure -N(R15)(R16)(R17), a N containing heteroary! group, or a H containing heterocyciyl group.
• R8 may contain a N atom, in one embodiment, the N atom is protonated such that the cationic functional group is a protonated amine.
• the lone pair of electrons on the nitrogen atom is used to form a bond with hydrogen thus providing a protonated amine.
• the N atom wiil have four covalent bonds wherein one of the bonds is with a hydrogen atom,
• R8 is an amino group
• the amino group may have the structure -N(R13)(R14).
• R13 and R14 are each independently hydrogen, a Ci-C 5 alky! group, a C1-C 5 a!keny! group, or - C(NR18)N ⁇ R19)(R20),
• R13, R14, or both are hydrogen, in another embodiment, R13, R14, or both are a C1-C 5 aikyl group, such as a Ci-C 3 a!kyl group, such as a methyl group, in another embodiment, R13, R14, or both may be -C(NR18)N ⁇ R19)(R20).
• R13 or R14 is -C(NR18)N(R19)(R20)
• the other may be hydrogen.
• R8 contains a guanidino group.
• the ammonium group may have the structure -
• R15, R18, and R17 are each independently hydrogen, a C1-C 5 alkyi group, a C C 5 aikenyi group, or -C(NR18)N(R19)(R20), wherein at least one of R15, R16, or R17 is hydrogen.
• R15, R16, R17, or ail three are hydrogen, in another embodiment, any one or two of R15, R16, or R17 is a C -C 5 alky! group, such as a C1-C 3 aiky! group, such as a methyl group.
• any one of R15, R18, or R17 is -C ⁇ NR18)N(R19)(R20), In such embodiments, R8 contains a guanidino group.
• R18, R19, and R20 are each independently hydrogen, a Ci-C 5 aikyl group, or a C1-C 5 alkenyi group, in one embodiment, R18, R19, R20, or all three are hydrogen.
• the guanidino group may be protonated.
• the nitrogen atom connected to the carbon atom via a double bond may further contain an additional hydrogen atom.
• the guanidino group may have the structure - C(NR18R21)N(R19)(R20) wherein R21 is hydrogen,
• the heteroaryl group may be any N containing heteroaryl group capable of providing a cationic functional group,
• the N containing heteroaryl group may be an imidazoly! group, a pyridyl group, a puriny! group, a pyrazolyl group, or a combination thereof.
• the N containing heteroaryl group is an imidazo!yl group.
• the N within R8 group is protonated to provide a protonated amine and thereby a cationic functional group.
• the amine within R8 may be a primary amine, a secondary amine, or a tertiary amine.
• a primary amine is referred to as an amine where only one of the hydrogens is replaced by an alkyi group or an aromatic group.
• a secondary amine is referred to as an amine where only two of the hydrogens are replaced by an a!kyi group and/or an aromatic group.
• a tertiary amine is referred to as an amine wherein three of the hydrogens are replaced by an aikyl group and/or an aromatic group, In one particular
• a primary amine is protonated to provide the protonated amine and the cationic functionality to the cationic monomer.
• the hydrophobic functional group may be contained within R12,
• R12 may be a Ci-C 20 alkyi group, a C2-C 20 aikylene group, an aryi group, or a heteroaryl group.
• R12 is a Ci-C 20 alkyi group, such as a C5-C 20 aikyl group.
• R12 is an aryi group or a heteroaryl group capable of providing a hydrophobic functional group.
• the ar/l group is a single an/I ring or a multiple fused aryl ring system, comprising two or more ring systems
• the aryl group is a single aryl ring such as a phenyl ring
• the aryi group is a fused aryl ring such as a naphthyl group or an anihryl group.
• the aryi group is a heteroaryl group.
• the heteroaryl group may be a multiple fused heteroaryl ring system such as an indolyi group or an isoindolyl group, in one particular embodiment, the aryi group and/or beteroary! group comprises a 6-membered carbon ring, such as a 8-membered aromatic carbon ring.
• R7 is connected to R8 which contains the cationic functional group.
• R7 is a direct bond between the C and R8, a Ci-C 5 alkyi group, or a C1-C 5 alkenyl group, in one embodiment, R7 is a C1-C 5 alkyi group, such as a C-i-C alkyi group, such as a butyl group.
• R11 is connected to R12 which contains the hydrophobic functional group.
• R11 is a direct bond between the C and R12, a C1-C 5 alkyi group, or a C1-C 5 alkenyl group.
• R11 is a Ci-C 5 alkyi group, such as a d-C 3 alkyi group, such as a methyl group.
• R9 and R10 are each independently hydrogen, a Ci-C 10 alkyi group, or a Ci-C 10 alkenyl group.
• R9 and R10 may be the same or they may be different.
• R9, R10, or both are hydrogen.
• R9, R10, or both are a Ci-C 10 alkyi group, such as a Ci-C 5 alkyi group, such as a CrC 3 alkyi group, such as a methyl or ethyl group.
• R9 or R10 When R9 or R10 is hydrogen, the respective monomer is in a free acid form wherein the carboxylic acid is not reacted or esterified. However, when RS or R10 contains an alky! group or an alkyiene group, the monomer may be considered esterified. As such, the carboxylic acid is reacted to form an ester. When in an ester form, the monomers may be esterified using any esterification reaction known in the art.
• the ester form of monomers further enhances the ability of the cationic polymer to interact with the negatively charged cell walls of bacteria.
• the cationic polymer when the cationic polymer is present in a free acid form wherein the carboxylic acid of the amino acid is not esterified, the hydrogen of the hydroxyl moiety of the carboxylic acid may be released thereby forming a negatively charged carboxylate. Accordingly, the negatively charged carboxylate may not interact with the negatively charged cell walls of bacteria and may in fact result in repulsion of such bacteria.
• the carboxylic acid is esterified with an aikyl group, the alkyi group may remain uncharged and thus may not negatively affect the interactions with the negatively charged ceil walls of bacteria.
• X and Y are each independently an amide (- C ⁇ 0)NH- or -NHC(O)-) or a carboxylic ester (-C(O)O- or -OC(0)-).
• X or Y is an amide (- C(0 ⁇ NH- or -NHC(O)-)
• the respective monomer may be referred to as an acryiamide monomer
• an acryiamide monomer may constitute an acryiamide, a methacrySamide, a derivative thereof, or a combination thereof.
• an acry!ate monomer or an acryiate ester monomer may be referred to as an acry!ate monomer or an acryiate ester monomer.
• an aerylaie monomer or acrylale ester monomer may be produced from acrylic acid or an acry!ate, methacry!ic acid or a methacry!ate, a derivative thereof, or a combination thereof,
• the cationic functional group and hydrophobic functional group are provided within the polymer so that they are capable of interacting with microorganisms, such as bacteria.
• the functional groups are provided as pendant groups branching from the main chain.
• the functional groups may be connected to the backbone of the cationic polymer b a spacer having a specific length, in general, the spacer arm length is the distance of the cationic functional group or the hydrophobic functional group from the polymer backbone. Accordingly, the spacer arm length is the length of the extension of the monomer due to the second constituent, such as the amino acid.
• the spacer arm length is the distance from R8 to X.
• the spacer length of the cationic functional group of the cationic monomer may be from about 3 A to about 30 A, in another embodiment from about 4 A to about 20 A, and in a particular embodiment from 5 A to about 15 A.
• the spacer arm length is the distance from R12 to Y,
• the spacer length of the hydrophobic functional group of the hydrophobic monomer may be from about 2 A to about 30 A, in another embodiment from about 3 A to about 20 A, and in a particular embodiment from 4 A to about 15
• the cationic polymer may be applied to a fibrous web prior to use, Such fibrous webs may be used to reduce microbial or viral populations on a hard surface (e.g., sink, fable, counter, sign, and so forth) or surface on a user/patient (e.g., skin, mucosal membrane, such as in the mouth, nasai passage, stomach, vagina, etc., wound site, surgical site, and so forth).
• the fibrous web may also be used to reduce microbial or viral populations by acting as a filter.
• the fibrous web may provide an increased surface area to facilitate contact of the cationic polymer with microorganisms.
• the fibrous ⁇ /eb may also serve other purposes, such as providing water absorption, barrier properties, etc.
• the fibrous web may also eliminate microorganisms through frictiona! forces imparted to the surface,
• the fibrous web may be provided in a variety of different forms, such as facial tissue, bath tissue, paper towels, napkins, absorbent articles, covers, wraps, and so forth. These webs may be formed from any of a variety of materials as Is well known in the art.
• the fibrous web may contain a plurality of absorbent fibers,
• the absorbent fibers may be formed by a variety of pulping processes, such as kraft pulp, sulfite pulp, thermomechanica! pulp, etc,
• the pulp fibers may include softwood fibers having an average fiber length of greater than 1 mm and particularly from about 2 to 5 mm based on a length-weighted average.
• Such softwood fibers can include, but are not limited to, northern softwood, southern softwood, redwood, red cedar, hemlock, pine (e.g., southern pines), spruce (e.g., black spruce), combinations thereof, and so forth, Exemplary commercially available pulp fibers suitable include those available from Kimberly-Clark Corporation under the trade designations "Longlac-19".
• Hardwood fibers such as eucalyptus, maple, birch, aspen, and so forth, can also be used, in certain instances, eucalyptus fibers may be particularly desired to increase the softness of the web, Eucalyptus fibers can also enhance the brightness, increase the opacity, and change the pore structure of the web to increase its wicking ability.
• secondary fibers obtained from recycled materials may be used, such as fiber pulp from sources such as, for exampie, newsprint, reclaimed paperboard, and office waste, Further, other natural fibers can also be used, such as abaca, sabai grass, milkweed floss, pineapple leaf, bamboo, algae, and so forth.
• synthetic fibers can also be utilized.
• the absorbent fibers may be integrated with synthetic fibers to form a composite.
• Synthetic thermoplastic fibers may also be employed in the nonwoven web, such as those formed from poiyolefins, e.g., polyethylene, polypropylene, polybufyiene, etc;
• polyesters e.g., polyethylene terephthalate and so forth; polyvinyl acetate; polyvinyl chloride acetate; polyvinyl bufyral; acrylic resins, e.g., poiyacryiate, polymethylacrylate, polymethylmethacrylate, and so forth; polyamides, e.g., nylon; polyvinyl chloride; poiyvinyisdene chloride; polystyrene; polyvinyl alcohol; poiyurethanes; polylactic acid; polyhydroxyalkanoate;
• thermoplastic fibers are inherently hydrophobic (i.e., non-wettab!e)
• such fibers may optionally be rendered more hydrophi!ic (i.e., wetfable) by treatment with a surfactant solution before, during, and/or after web formation.
• surfactant solution i.e., wetfable
• Other known methods for increasing wettability may also be employed, such as described in U.S. Patent No. 5,057,361 to Sayovitz, et al tie which is incorporated herein in its entirety by reference thereto for ail purposes.
• the relative percentages of such fibers may vary over a wide range depending on the desired characteristics of the composite.
• the composite may contain from about 1 wt.% to about 80 wt.%, in some embodiments from 5 wt.% to about 50 wt.%, and in some embodiments, from about 10 wt.% to about 40 wt.% synthetic polymeric fibers.
• the composite may likewise contain from about 40 wt.% to about 99 wt.%, in some embodiments from 50 wt.% to about 95 wt.%, and in some embodiments, from about 60 wt.% to about 90 wt.% absorbent fibers.
• a nonwoven composite may be formed that is a "coform material” that contains a mixture or stabilized matrix of thermoplastic fibers and a second non-thermoplastic material.
• coform materials may be made by a process in which at least one meitb!own die head is arranged near a chute through which other materials are added to the web while it is forming.
• Such other materials may include, but are not limited to, fibrous organic materials such as woody or non-woody pulp such as cotton, rayon, recycled paper,131p fluff and also superabsorbent particles, inorganic and/or organic absorbent materials, treated polymeric staple fibers and so forth.
• the nonwoven composite may be formed be formed by hydraulically entangling staple length fibers and/or filaments with high-pressure jet streams of water.
• Various techniques for hydraulically entangling fibers are generally are disclosed, for example, in U.S. Patent Nos, 3,494,821 to Evans and 4,144,370 to Bouoiton, which are incorporated herein in their entirety by reference thereto for all purposes.
• Hydraulically entangled nonwoven composites of continuous filaments (e.g., spunbond web) and natural fibers (e.g., pulp) are disclosed, for example, in U.S. Patent Nos. 5,284,703 to Everhart, et al. and 6,315,864 to Anderson ⁇ et at which are incorporated herein in their entirety by reference thereto for ail purposes. Hydraulically entangled nonwoven composites of staple fiber blends (e.g., polyester and rayon) and natural fibers (e.g., pulp), also known as
• hydroentangied webs can also contain synthetic and pulp fibers.
• Hydroentangied webs refer to webs that have been subjected to columnar jets of a fluid that cause the fibers in the web to entangle. Hydroentangiing a web typically increases the strength of the web, in one embodiment, pulp fibers can be hydroentangied into a continuous filament material, such as a spunbond web, The hydroentangied resulting nonwoven composite may contain pulp fibers In an amount from about 50% to about 80% by weight, such as in an amount of about 70% by weight.
• Commercially available hydroentangied composite webs as described above are commercially available from the Kimberly-Clark Corporation under the name HYDROKNIT. Hydraulic entangling is described in, for example, U.S. Patent No. 5,389,202 to Everhart, which is incorporated herein in its entirety by reference thereto for all purposes.
• the cafionic polymer may be incorporated into synthetic webs such as a meitbiown web, a spunbond web, and laminates thereof.
• meltb!own fibers refers to fibers formed by extruding a molten thermoplastic material through a plurality of fine, usually circular, die capillaries as molten threads or filaments into converging high velocity, usually hot, gas (e.g. air) streams which attenuate the filaments of thermoplastic material to reduce their diameter, which may be to microfiber diameter. Thereafter, the meitbiown fibers are carried by the high velocity gas stream and are deposited on a collecting surface to form a web of randomly disbursed meitbiown fibers.
• gas e.g. air
• Meitbiown fibers are microfibers which may be continuous or discontinuous, are generally smaller than 10 microns in average diameter, and are generally tacky when deposited on a collecting surface.
• spunbond fibers refers to small diameter fibers which are formed by extruding molten thermoplastic material as filaments from a plurality of fine, usually circular capillaries of a spinneret with the diameter of the extruded filaments then being rapidly reduced as by, for example, in U.S. Patent No. 4,340,563 to Appel. et al balance U.S. Patent No. 3,692,818 to Dorschner. et al., U.S. Patent No, 3,802,817 to Matsuki, et ah, U.S. Patent No. 3,338,992 to Kinney, U.S. Patent No. 3,341 ,394 to Kinney, U.S.
• Spunbond fibers are generally not tacky when they are deposited on a collecting surface. Spunbond fibers are generally continuous and have average diameters (from a sample of at least 10) larger than 7 microns, and more particularly, between about 10 and 40 microns.
• Laminates containing meitbiown webs and spunbond webs include, for instance,
• SMS laminates spunbond/meltblown/spunbond laminates
• These laminates may be made by sequentially depositing layers onto a moving, forming surface.
• an SMS laminate may be made by depositing onto a moving, forming belt first a spunbond web, then a meitbiown web, and then a spunbond web and bonding the layers.
• These layers may be bonded by thermal point bonding, adhesive bonding, hydroentangeimenf, needling, ultrasonic bonding, and the like.
• Such processes are disclosed, for example, in U.S. Patent No. 4,041 ,203 to Brock et ai., U.S. Patent No.
• the basis weight of the web Is typically from about 20 to about 200 grams per square meter ("gsm"), and in some embodiments, between about 35 to about 100 gsm. Lower basis weight products may be particularly weli suited for light duty uses, while higher basis weight products may be better adapted for heavy duty
• the fibrous web may assume a variety of shapes, including but not limited to, generally circular, oval, square, rectangular, or irregularly shaped, in one embodiment, the web may be presented in the form of a wipe wherein the web is substantially saturated with a solution containing the cationic polymer.
• Each individual wipe may be arranged in a folded configuration and stacked one on top of the other to provide a stack of wipes.
• Such folded configurations are well known to those skilled in the art and include c-folded, z-foided, quarter-folded configurations and so forth.
• the wipe may have an unfolded length of from about 2.0 to about 80.0 centimeters, and in some embodiments, from about 10.0 to about 25.0 centimeters.
• the wipes may likewise have an unfolded width of from about 2.0 to about 80.0 centimeters, and in some embodiments, from about 10.0 to about 25.0 centimeters.
• the stack of folded wipes may be placed in the interior of a container, such as a plastic tub, to provide a package of wipes for eventual sale to the consumer.
• the wipes may include a continuous strip of material which has perforations between each wipe and which may be arranged in a stack or wound into a roll for dispensing.
• a container such as a plastic tub
• the cationic polymer may be applied to the fibrous web in the form of a solution.
• the exact quantity of the polymer employed may vary based on a variety of factors, including the presence of other additives, the suspected concentration of the microorganism, etc., it is typically present in the solution in an amount of from about 0.01 wt. % to about 20 wt, % and in some embodiments from about 0.1 wt. % to about 10 wt. %.
• the polymer may be incorporated into the fibrous web during its formation or simply coated onto ail or a portion of a surface of the fibrous web using known techniques, such as printing, dipping, spraying, melt extruding, coating (e.g., solvent coating, powder coating, brush coating, etc.), foaming, and so forth, in one embodiment, for example, the solution is applied to the fibrous web by dipping, spraying, or printing, if desired, the solution may be applied in a pattern that covers from about 5% to about 95%, in some embodiments from about 10% to about 90%, and in some embodiments, from about 20% to about 75% of a surface of the fibrous web. Such patterned application may have various benefits, Including enhanced aesthetic appeal, improved absorbency, etc.
• the particular type or style of the pattern is not a limiting factor of the invention, and may include, for example, any arrangement of stripes, bands, dots, or other geometric shape.
• the pattern may include indicia (e.g., trademarks, text, and logos), fioral designs, abstract designs, any configuration of artwork, etc. it should be appreciated that the "pattern" may take on virtually any desired appearance.
• the solution may be applied using rotogravure or gravure printing, either direct or indirect (offset).
• Gravure printing encompasses several well-known engraving techniques, such as mechanical engraving, acid-etch engraving, electronic engraving and ceramic laser engraving. Such printing techniques provide excellent control of the composition distribution and transfer rate. Gravure printing may provide, for example, from about 10 to about 1000 deposits per lineal inch of surface, or from about 100 to about 1 ,000,000 deposits per square inch. Each deposit results from an individual ceil on a printing roil, so that the density of the deposits corresponds to the density of the cells. A.
• suitable electronic engraved example for a primary delivery zone is about 200 deposits per lineal inch of surface, or about 40,000 deposits per square inch.
• Suitable gravure printing techniques are also described in U.S. Pat. No. 6,231 ,719 to Garvey, et al tie which is incorporated herein in its entirety by reference thereto for all purposes.
• other printing techniques such as fiexographlc printing, may also be used.
• Still another suitable contact printing technique that may be utilized is "screen printing.”
• Screen printing is performed manually or photomechanicaliy.
• the screens may include a silk or nylon fabric mesh with, for instance, from about 40 to about 120 openings per lineal centimeter.
• the screen material is attached to a frame and stretched to provide a smooth surface.
• the stencil is applied to the bottom side of the screen, i.e., the side in contact with the substrate upon which the formulation(s) are to be printed.
• the formulation(s) are painted onto the screen, and transferred by rubbing the screen (which is in contact with the substrate) with a squeegee.
• Ink-jet printing techniques may also be employed.
• Ink-jet printing is a non-contact printing technique that involves forcing the ink through a tiny nozzle (or a series of nozzles) to form droplets that are directed toward the substrate.
• Two techniques are generally utilized, i.e., "DOD" (Drop-On- Demand) or "continuous" ink-jet printing.
• DOD Drop-On- Demand
• continuous systems ink is emitted in a continuous stream under pressure through at least one orifice or nozzle. The stream is perturbed by a pressurization actuator to break the stream into droplets at a fixed distance from the orifice.
• DOD systems use a pressurization actuator at each orifice to break the ink into droplets.
• the pressurszaiion actuator in each system may be a piezoelectric crystal, an acoustic device., a thermal device, etc.
• the selection of the type of ink jet system varies on the type of material to be printed from the print head. For example, conductive materials are sometimes required for continuous systems because the droplets are deflected electrostatically.
• any other suitable application technique may be used.
• other suitable printing techniques may include, but not limited to, such as laser printing, thermal ribbon printing, piston printing, spray printing, fiexographic printing, etc.
• Still other suitable application techniques may include bar, roil, knife, curtain, spray, slot-die, dip- coating, drop-coating, extrusion, stencil application, etc. Such techniques are well known to those skilled in the art.
• the fibrous web may be dried at a certain temperature to drive the solvents from the solution and form a concentrate.
• solution concentrates generally have a very high stability in storage.
• water or an aqueous solution may simply be added. Drying may be accomplished using any known technique, such as an oven, drying rolls (e.g., through-air drying, Yankee dryer), etc.
• the temperature at which the fibrous web is dried generally depending on the time period over which it is dried, but is typically at least about 20°C, and in some embodiments, from about 30°C to about 100°C. Drying may occur either before or after the solution is applied to the fibrous web.
• the solvent content (e.g., water content) of the resulting concentrate is thus typically less than about 5 wt.%, in some embodiments less than about 2 wt.%, and in some embodiments less about 1 wt.%,
• the solids add-on level of the solution on the fibrous web is typically from about 5% to about 100%, in some embodiments from about 10% to about 80%, and in some embodiments from about 15% to about 70%.
• the "solids add-on level" Is determined by subtracting the weight of the untreated substrate from the weight of the treated substrate (after drying), dividing this calculated weight by the weight of the untreated substrate, and then multiplying by 100%. Lower add-on levels may provide optimum functionality of the substrate, while higher add-on levels may provide optimum antimicrobial efficacy.
• the solution may also be in the form of a liquid. This may be accomplished by simply not drying the solution after it is applied to the fibrous web. While the solids add-on level of such "wet wipes" generally remain within the ranges noted above, the total amount of the solution employed in such "wet wipes" (including any solvents) depends in part upon the type of web material utilized, the type of container used io store the wipes, the nature of the solution, and the desired end use of the wipes, Generally, however, each wet wipe contains from about 150 wt.% to about 600 t.%, and desirably from about 300 wt.% to about 500 t.% of the solution based on the dry weight of the web or wipe.
• the cationic poiymer may be employed to capture and retain microorganisms, such as bacteria (including cyanobacteria and Mycobacteria), protozoa, algae, and fungi (e.g., molds and yeast), viruses, prions, and other infectious particies.
• bacteria including cyanobacteria and Mycobacteria
• protozoa including cyanobacteria and Mycobacteria
• algae including cyanobacteria and Mycobacteria
• fungi e.g., molds and yeast
• viruses prions, and other infectious particies.
• the cationic polymer may be employed to capture and retain several medically significant bacteria groups, such as Gram negative rods (e.g., Entereobacteria): Gram negative curved rods (e.g., Helicobacter : Campylobacter, etc.); Gram negative cocci (e.g., Neisseria): Gram positive rods (e.g., Bacillus, Clostridium, etc.); Gram positive cocci (e.g., Staphylococcus, Streptococcus, etc.); obligate intracellular parasites (e.g...
• Gram negative rods e.g., Entereobacteria
• Gram negative curved rods e.g., Helicobacter : Campylobacter, etc.
• Gram negative cocci e.g., Neisseria
• Gram positive rods e.g., Bacillus, Clostridium, etc.
• Gram positive cocci e.g., Staphylococcus, Streptococcus
• Rickettsia and Chlamydia acid fast rods (e.g., Mycobacterium, Nocardia, etc.); spirochetes (e.g., Treponema, Boreltia, etc.); and mycoplasmas (i.e., bacteria that lack a cell wall).
• acid fast rods e.g., Mycobacterium, Nocardia, etc.
• spirochetes e.g., Treponema, Boreltia, etc.
• mycoplasmas i.e., bacteria that lack a cell wall.
• bacteria that may be captured and/or retained with the cationic polymer of the present invention include Escherichia coii (Gram negative rod), Klebsiella pneumoniae (Gram negative rod), Streptococcus (Gram positive cocci), Salmonella choleraesuis (Gram negative rod), Salmonella typhimunum (Gram negative rod), Staphyioccus aureus (Gram positive cocci), and P. aeruginosa (Gram negative rod), in addition to bacteria, other microorganisms of interest include fungi (e.g., Aspergillus niger) and yeasts (e.g., Candida albicans),
• fungi e.g., Aspergillus niger
• yeasts e.g., Candida albicans
• two cationic polymers were prepared: Polymer 1 and Poiymer 2.
• Poiymer 1 is in a free acid form wherein the carboxyl group of the amino acid side group is presented as a carboxyiic acid.
• Polymer 2 is in an ester form wherein the carboxyl group of the amino acid side group remains esterified, such as modified to provide a methyl group.
• Polymer 1 and Polymer 2 below were synthesized using Monomer A and Monomer B.
• Polymer 1 was prepared by combining Monomer A and Monomer B with an initiator., azobisisobutyronitriie, and a solvent, isopropanol. The contents were purified under nitrogen for 0.5 hours. Polymerization was conducted at a temperature of 70 °C for approximately 24 hours under a nitrogen atmosphere and agitation. Then, to stop polymerization, 2 mL of tetrahydrofuran were added to the mixture. The polymer mixture was poured into 200 mL of n-hexane allowing the polymer to precipitate. The precipitate was separated via filtration under a reduced pressure.
• an initiator. azobisisobutyronitriie
• solvent isopropanol
• the precipitate was combined with 5 mL of dichloromethane and 2 mL of trifluoroacetic acid in a round bottom flask equipped with a liquid sea!. The mixture was stirred at room temperature for 30 minutes. The solvent was removed via rotary evaporation under reduced pressure. The residue was dissolved in 5 mL of tetrahydrofuran. The mixture was combined with 200 mL of n-hexane allov/ing the polymer to precipitate. The precipitated product was filtered under reduced pressure. The final product was collected and dried under vacuum.
• Polymer 2 was prepared by combining Monomer A and Monomer B with an initiator, azobisisobufyronitriie, and a solvent, isopropanoi. The contents were purified under nitrogen for 0,5 hours. Polymerization was conducted at a temperature of 70 °C for approximately 24 hours under a nitrogen atmosphere and agitation. Then, to stop polymerization, 2 mL of tetrahydrofuran were added to the mixture. The polymer mixture was poured into 200 mL of n-hexane aliowing the polymer to precipitate. The precipitate was separated via filtration under a reduced pressure.
• the precipitate was combined with 20 mL of anhydrous ethyl acetate in a three-necked round bottom flask equipped with a liquid seal, thermometer, and an air duct. The flask was placed in an ice bath to keep the reaction temperature below 0 °C and dry hydrogen chloride gas was passed through the vessel for 0.5 hours. The precipitated product was filtered under reduced pressure. The final product was collected and dried under vacuum.
• lipopolysaccharlde extract with phosphate buffered solution (PBS) at a ratio of 1 :1.
• PBS phosphate buffered solution
• the samples were incubated at ambient temperature for 10 minutes and then centrifuged for 5 minutes at 9000 rpm. The supernatant was collected and analyzed using an LAL ⁇ Umuius Amebocyte Lysate) Chromogenic Assay kit from Thermo Scientific Pierce according to the manufacturer ' s instructions.
• the amount of LPS present in the supernatant of the PBS control sample was compared to the supernatant of the samples containing Polymer A or Polymer B.
• the supernatant samples containing the cationic polymers contained at least 30% less LPS of £ coli and LPS of Salmonella.
• Samples were prepared by mixing 50 L of a ceil suspension (1 : 10000 dilution of overnight culture) with a 50 ⁇ . polymer suspension or a phosphate buffered solution control. The mixtures were incubated at room temperature for 5 minutes. The suspensions were diluted 10-fold with 900 ⁇ . using maximum recovery diluents (RD). The dilutions were plated onto a lysogeny broth (LB) agar plate using the spread plate method. The plates were incubated at 37 °C for up to 48 hours. The colony forming units were counted and analyzed based on ihe log reduction of the control.
• RD maximum recovery diluents
• test cultures were prepared by inoculating a single colony of bacteria into 10 ml of a lysogeny broth (LB) and incubating at 37 T and 200 rpm overnight. The overnight culture may be washed by phosphate buffered solution twice, if necessary. Then a 1 :10000 or 1 :100 dilution in phosphate buffer with 5% (v/v) fetal bovine serum is prepared,
• VIVA® (Kimberly-Clark) paper to Stamm were cut into 1 cm 2 and placed into a 24 well microplate.
• each polymer solution was added to a respective sample.
• the samples were allowed to dry at ambient temperature overnight.
• 20 ⁇ JI of each solution was added in a checkerboard pattern over the surface of the respective sample.
• the samples were inoculated at ambient temperature for 1 minute.
• the inoculated samples were placed in a separate 50 mL centrifuge tube with 5 mL phosphate buffered solution. The mixtures were agitated gently by swirling the tubes for 10 seconds. Dilutions were prepared and enumerated using the spread piate method. The mixtures were incubated at 37 °C for up to 48 hours. The colony forming units were counted and analyzed based on the log reduction of the control.
• the following tables provide the colony-forming unit(CFU)/mL
• the colony-forming unit is an estimate of viable bacteria.
• the fables provide an indication of the amount of colonies released and trapped within the cationic polymers.
• the tables provide the ability of the webs containing the cationic polymers to reduce the amount of bacteria or microorganisms from a surface or liquid.
• the web containing Polymer 1 was capable of trapping at least 90% while the web containing Polymer 2 was capable of trapping at least 85% of the LPS of E. coii.
• the web containing Polymer 1 was capable of trapping at least 90% of the LPS of Salmonella
• the web containing Polymer 2 was capable of trapping at least 85% (with a sample concentration of 10 mg/mL) and at least 90% ⁇ with a sample concentration of 20 mg/rnL) of the LPS of Salmonella

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