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WO2018232000A1 - Désinfectant de surface ayant une propriété biocide résiduelle - Google Patents

Désinfectant de surface ayant une propriété biocide résiduelle Download PDF

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Publication number
WO2018232000A1
WO2018232000A1 PCT/US2018/037354 US2018037354W WO2018232000A1 WO 2018232000 A1 WO2018232000 A1 WO 2018232000A1 US 2018037354 W US2018037354 W US 2018037354W WO 2018232000 A1 WO2018232000 A1 WO 2018232000A1
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WO
WIPO (PCT)
Prior art keywords
weight
formulation
wipe
wipe according
quaternary ammonium
Prior art date
Application number
PCT/US2018/037354
Other languages
English (en)
Inventor
Tian Lan
Samuel James HANNA
Gina Parise SLOAN
Brian Patrick Aylward
Karen Terry WELCH
Dennis Earl SHIREMAN
Kevin Andrew KAVCHOK
Charles L. Hawes
Jesse Douglas TURMENNE
Matthew Michael PETKUS
Original Assignee
W.M. Barr & Company, Inc.
Microban Products Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US15/625,612 external-priority patent/US10925281B2/en
Application filed by W.M. Barr & Company, Inc., Microban Products Company filed Critical W.M. Barr & Company, Inc.
Priority to JP2019565448A priority Critical patent/JP2020523293A/ja
Priority to RU2020101126A priority patent/RU2020101126A/ru
Priority to MX2019015269A priority patent/MX2019015269A/es
Priority to CN201880039705.0A priority patent/CN110868858A/zh
Priority to CA3063749A priority patent/CA3063749A1/fr
Priority to BR112019026250-4A priority patent/BR112019026250A2/pt
Priority to EP18818125.9A priority patent/EP3638027A4/fr
Publication of WO2018232000A1 publication Critical patent/WO2018232000A1/fr

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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
    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/20—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61—Polyamines polyimines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic

Definitions

  • the present invention relates to the field of disinfectant formulations, and more specifically, to a disinfectant formulation imparting a residual biocidal property.
  • a hospital-acquired infection is an infection whose development is favored by a hospital or healthcare environment.
  • Such maladies typically are fungal or bacterial infections and can afflict the victim locally or systemically.
  • Nosocomial infections can cause severe pneumonia as well as infections of the urinary tract, bloodstream, and other parts of the body.
  • a trio of pathogens is commonly found in healthcare settings and together account for approximately one-third of nosocomial infections: coagulase-negative Staphylococci (15%), Candida species (11%), and Escherichia coli (10%).
  • ESKAPE pathogens Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter species - possess antibiotic resistance and are implicated in nearly half of all nosocomial infections. Their resistance to one or more biocidal agents makes such infections particularly dangerous.
  • the broad nutritional versatility of Pseudomonas permits its survival in extreme environments, including survival on surfaces not intensively cleaned and sterilized.
  • This pathogen's ubiquity in the hospital environment makes it a leading cause of Gram-negative nosocomial infections.
  • Particularly vulnerable are immune- compromised patients (e.g. those afflicted with cystic fibrosis, cancer, or burns).
  • Direct contact transmission involves a patient contacting either a contaminated patient or worker.
  • care providers move through the healthcare institution, they come into contact with its many patients.
  • These workers unwittingly act in a manner analogous to bees in a garden, "pollinating" rooms and wards as they care for residents.
  • Indirect contact transmission occurs when the patient contacts a contaminated object or surface.
  • the healthcare environment presents an array of articles capable of passively vectoring pathogens.
  • Nosocomial infections further deal a serious blow to the volume, quality, and cost of healthcare provided by hospitals and other institutions.
  • HAI-related deaths occurring annually in the United States, an estimated two million more victims are forced to endure the physical ravages and emotional distress associated with these serious and avoidable illnesses.
  • Household environments also face microbes.
  • a main disadvantage associated with consumer disinfectants and sanitizers is that, while they can be effective at initially killing microbes, the surface is easily and quickly re-contaminated through contact, airborne microbes, and un-killed residual microbes before treatment. While some of the disinfectants would continue to offer some control if simply left on the surface, this would result in a greasy or tacky residue that would be easily negated by casual contact with the surface.
  • a home care and household cleaner that kills microbes quickly on contact, then acts as a residual disinfectant but yet does not have this undesirable sticky or tacky effect.
  • Such cleaners may be useful for general purpose household cleaning, bathroom cleaning, and spray protectants.
  • VOC volatile organic content
  • a biofilm is generally defined as a layer of microorganisms adhering to the surface of a structure, which may be organic or inorganic, that secrete a protective coating that is biological in origin.
  • Biofilms present a large problem for public health because of increased resistance of biofilm-associated organisms to antimicrobial agents and for the potential of biofilm borne organisms to cause infections.
  • Current disinfectants do not have the ability to kill biofilms or to seal or lock-in biofilms on surfaces to prevent cross- contamination events and to prevent out growth.
  • There are limited solutions for surface biofilm problems For example, there is a building body of evidence that surface biofilms pose a problem in the healthcare setting for the above mentioned reasons.
  • biofilms are a recognized problem of possible contamination within the food industry. Other industries face similar concerns.
  • a solution targeted at potential biofilm problem areas that can be used to eradicate biofilms.
  • the residual biocidal property prefferably associated with the treated surface, such that it may continue to provide microbial reduction for an extended period of time after application.
  • the present invention relates to a disinfectant formulation imparting a residual biocidal property.
  • the disinfectant formulation comprises a polymer binder, wherein the polymer binder is an oxazoline homopolymer or an extended or a modified polymer based on an oxazoline homopolymer, and a biocidal compound.
  • the disinfectant formulation further comprises a carrier.
  • the oxazoline homopolymer has a structure of: wherein Ri is a hydrogen, alkyl, alkenyl, alkoxy, alkylamino, alkynyl, allyl, amino, anilino, aryl, benzyl, carboxyl, carboxyalkyl, carboxyalkenyl, cyano, glycosyl, halo, hydroxyl, oxazolinium mesylate, oxazolinium tosylate, oxazolinium triflate, silyl oxazolinium, phenolic, polyalkoxy, quaternary ammonium, thiol, or thioether group; R 2 is a hydrogen, alkyl, alkenyl, alkoxy, alkylamino, alkynyl, allyl, amino, anilino, aryl, benzyl, carboxyl, carboxyalkyl, carboxyalkenyl, cyano, glycos
  • an article having the disinfectant formulation(s) of the present invention is provided as well as methods of making, using and applying the disinfectant formulation(s).
  • microbe or “microbial” should be interpreted to refer to any of the microscopic organisms studied by microbiologists or found in the use environment of a treated article. Such organisms include, but are not limited to, bacteria and fungi as well as other single-celled organisms such as mold, mildew and algae. Viral particles and other infectious agents are also included in the term microbe.
  • Antimicrobial further should be understood to encompass both microbicidal and microbistatic properties. That is, the term comprehends microbe killing, leading to a reduction in number of microbes, as well as a retarding effect of microbial growth, wherein numbers may remain more or less constant (but nonetheless allowing for slight increase/ decrease) .
  • antimicrobial to denote a broad spectrum activity (e.g. against bacteria and fungi).
  • efficacy against a particular microorganism or taxonomic rank the more focused term will be used (e.g. antifungal to denote efficacy against fungal growth in particular).
  • the present invention is directed to a disinfectant formulation.
  • the disinfectant formulation is in a liquid form.
  • the composition of the disinfectant formulation comprises a biocidal compound and a polymer binder.
  • the composition may further comprise a solvent (such as water or a low molecular weight alcohol), a surfactant, a colorant, a fragrance, among other components.
  • a liquid composition is formulated having surface disinfection and residual biocidal properties.
  • the formulation can be applied to a surface by spraying, rolling, fogging, wiping or other means.
  • the formulation acts as a surface disinfectant, killing infectious microbes present on the surface.
  • the liquid formulation leaves a residual protective film on the surface.
  • the residual film possesses a biocidal property, enabling it to maintain protection of the surface against microbial contamination for an extended time period after its application.
  • the surface disinfectant formulation imparts a film with the capacity to quickly kill bacteria and other germs for at least 24 hours after deposit of the film on the treated surface.
  • quick kill generally refers to a time period of about 30 seconds to about 5 minutes. The film will remain on the surface and is durable to multiple touches and wearing of the surface.
  • the disinfectant formulation is a liquid composition comprising a polymer binder, a biocidal compound, a carrier such as a solvent, and other optional components such as fragrances.
  • the disinfectant formulation is a biofilm sealant.
  • the biofilm sealant once applied to a surface forms a polymer film.
  • the polymer film is applied wet and dries as a film layer to lock in and prevent subsequent outgrowth of biofilm microorganisms.
  • the biofilm sealant although preferably in the form of a liquid, may also take other forms such as a gel, or other form. Once the biofilm sealant is in place, the microbes of the biofilm have limited access to oxygen and exogenous nutrients.
  • the biofilm sealant has the potential to seal in bacteria but also to provide extended release of antimicrobials into the film to kill the microorganisms in the biofilm.
  • the biofilm sealant comprises a polymer binder and a biocidal compound.
  • the biocidal compound may include, but is not limited to, any biocidal compound set forth herein.
  • the biofilm sealant comprises an oxazoline homopolymer as the polymer binder.
  • the oxazoline homopolymer may have any of the structures as set forth herein.
  • the biofilm sealant comprises a polymer binder, a biocidal compound, and an enzyme(s).
  • the enzyme is to assist in degrading the biofilm and provide for enhanced antimicrobial penetration by the biocidal agent and ultimately biofilm removal.
  • Example enzymes include, but are not limited to, proteinase, DNase, RNase, and carbohydrate specific enzymes that can degrade the extracellular matrix associated with the biofilm.
  • the biofilm selant comprises a polymer binder and an antibody as a biological material for slow release into the film.
  • the antibody functionality will bind to the biofilm microbe to prevent cross-contamination.
  • the biofilm sealant comprises a polymer binder, and a bacteriophage or a mixture of bacteriophages as a biological material for slow release into the film.
  • the bacteriophage act as a targeted antimicrobial agent to kill biofilm associated organisms.
  • the biofilm sealant comprises a polymer binder, and a mixture of bacteriophages, antimicrobial agents, enzymes and antibodies as a biological material for slow release into the film.
  • the polymer binder is an oxazoline homopolymer.
  • the oxazoline homopolymer has the following structure:
  • Ri and R 2 are end groups determined by the polymerization techniques used to synthesize oxazoline homopolymer.
  • Ri and R 2 are independently selected and include, but are not limited to, hydrogen, alkyl, alkenyl, alkoxy, alkylamino, alkynyl, allyl, amino, anilino, aryl, benzyl, carboxyl, carboxyalkyl, carboxyalkenyl, cyano, glycosyl, halo, hydroxyl, oxazolinium mesylate, oxazolinium tosylate, oxazolinium triflate, silyl oxazolinium, phenolic, polyalkoxy, quaternary ammonium, thiol, or thioether groups.
  • R 2 could include a macrocyclic structure formed during synthesis as a consequence of intramolecular attack.
  • Ri is a methyl group and R 2 is oxazolinium tosylate if methyl tosylate is used as the initiator in the cationic initiated polymerization of oxazoline.
  • R 3 is an end group determined by the type of oxazoline used in the preparation of the polymer binder of this invention.
  • R3 includes, but is not limited to, hydrogen, alkyl, alkenyl, alkoxy, aryl, benzyl, hydroxyalkyl, or perfluoroalkyl.
  • R3 is an ethyl group if ethyloxazoline is the monomer used to prepare the polymer binder for the present invention.
  • n is the degree of oxazoline polymerization in the homopolymer. n is in a range of 1 to 1,000,000. Preferably, n is in a range of 500 to 250,000; most preferably, n is in a range of 2500 to 100,000.
  • extended or modified polymers with some variations based on the oxazoline homopolymer are also suitable for the present invention.
  • the techniques and options for performing chemical or molecular structure variations or modifications to oxazoline should be familiar to those skilled in the art.
  • a class of extended or modified polymers based on oxazoline homopolymer can be represented with the following molecular structure:
  • Ri and R 3 have the same definition as those given in the above oxazoline homopolymer.
  • B is additional monomer repeating unit linked to oxazoline in a coploymer.
  • the types of arrangement of the repeating units between B and oxazoline in the copolymer can include, but are not limited to, block, alternating, periodic, or combinations thereof. There is no limitation as to the types of B that can be used to copolymerize with or modify the oxazoline of the present invention.
  • n is the degree of polymerization for an oxazoline repeating unit; n in the copolymer is in a range of 1 to 1,000,000 and the degree of polymerization for B repeating unit in the copolymer m is in a range of 0 to 500,000 at the same time.
  • n is in a range of 500 to 250,000 and m is in a range of 20 to 10,000; and most preferably, n is in a range of 2500 to 100,000 and m is in a range of 50 to 5,000.
  • B could also be linked to oxazoline as an end group in a cationic polymerization by using B as a cationic initiator if B itself is already a quaternary ammonium compound.
  • B can be, for example, ethyleneimine with the following molecular structure:
  • Ri and R 2 end groups have the same definition as those outlined for oxazoline homopolymer.
  • R 3 includes, but is not limited to, hydrogen, alkyl, alkenyl, alkoxy, aryl, benzyl, hydroxyalkyl, or perfluoroalkyl.
  • R 4 includes, but is not limited to, hydrogen, alkyl, alkenyl, alkoxy, aryl, benzyl, hydroxyalkyl, or perfluoroalkyl.
  • m is in a range of 0 to 500,000; preferably, in a range of 20 to 10,000; and most preferably, in a range of 50 to 5,000.
  • n is in a range of 1 to 1,000,000; preferably, 500 to 250,000; most preferably, in a range of 2500 to 100,000.
  • oxazoline and ethyleneimine copolymer can be phased into two steps, for example.
  • a first step a cationic ring opening polymerization technique can be used to make polyoxazoline homopolymer.
  • the polyoxazoline made in the first step can be hydrolyzed to convert part of polyoxazoline repeating units into polyethyleneimine.
  • oxazoline-ethylenimine copolymer can be made with the appropriate respective monomers, an oxazoline and an aziridine. The result would be a cationic polymer having the above structure.
  • the degree of polymerization for oxazoline repeating unit n in the copolymer is in a range of 1 to 1,000,000 and the degree of polymerization for ethyl eneimine repeating unit in the copolymer m is in a range of 0 to 500,000 at the same time.
  • n is in a range of 500 to 250,000 and m is in a range of 20 to 10,000, and most preferably n is in a range of 2500 to 100,000 and m is in a range of 50 to 5,000.
  • the nitrogen in the ethyleneimine repeating unit could be further quaternized to generate the following cationic copolymer:
  • Ri, R 2 , R 3 and R 4 have the same meaning as those designated in the above oxazoline-ethyleneimine copolymer.
  • R 5 includes, but is not limited to, a hydrogen, methyl, ethyl, propyl, or other types of alkyl group.
  • the corresponding anion X " is a halogen, sulfonate, sulfate, phosphonate, phosphate, carbonate/bicarbonate, hydroxy, or carboxylate.
  • n and m are also the same as those described in oxazoline- ethyleneimine copolymer.
  • Polydiallyldimethylammonium chloride Another example of B that can be used for the present invention is polydiallyldimethylammonium chloride.
  • Polyethyloxazoline modified with polydiallyldimethylammonium chloride has the following structure:
  • Ri and R 4 have the same meaning as described in previous example for quaternized oxazoline-ethyleneimine copolymer.
  • R 2 and R 3 independently, include, but are not limited to, short chain alkyl groups such as Ci to C 6 .
  • the corresponding anion X " is a halogen, sulfonate, sulfate, phosphonate, phosphate, carbonate/bicarbonate, hydroxy, or carboxylate.
  • n and m are defined and numbered the same as in previous examples.
  • B could be other olefins including, but not limited to, diallyldimethylammonium chloride, styrene, methoxystyrene, and methoxyethene.
  • Ethyloxazoline can also be copolymerized with heterocyclic monomers such as oxirane, thietane, 1,3-dioxepane, oxetan-2-one, and tetrahydrofuran to enhance the performance of the polymer for the present invention.
  • the binder used in this invention could also employ pendant oxazoline groups on a polymer backbone, such as an acrylic or styrene based polymer, or a copolymer containing acrylic or styrene.
  • polyethyloxazolines examples include, but are not limited to, Aquazol 500 from Polymer Chemistry Innovations, Inc.
  • the amount of polymer binder that can be used in the liquid formulation can vary somewhat depending upon desired length of residual activity of the composition and the nature of all the other components in the composition.
  • the amount of polymer binder in the liquid formulation is in a range of 0.1% to 20% based on the weight of liquid formulation.
  • the amount of polymer binder in the liquid formulation is more preferably in a range of 0.5% to 10%, and most preferably in a range of 0.8% to 5%.
  • the amount of polymer binder in the liquid formulation is more preferably in a range of 0.1% to 10%, and most preferably in a range of 0.1% to 5%.
  • the polymer binder preferably is water-soluble and can be readily removed from surface if any buildup is noticed. Present in small amounts, it nonetheless can provide a durable bond between biocidal compound and the treated surface to facilitate residual efficacy.
  • the biocidal compound may be a quaternary ammonium compound (QAC) with the following molecular structure:
  • Ri, R 2 , R3, and R 4 are independently selected and include, but are not limited to, alkyl, alkoxy, or aryl, either with or without heteroatoms, or saturated or non-saturated. Some or all of the functional groups may be the same.
  • the corresponding anion X " includes, but is not limited to, a halogen, sulfonate, sulfate, phosphonate, phosphate, carbonate/bicarbonate, hydroxy, or carboxylate.
  • QACs include, but are not limited to, n-alkyl dimethyl benzyl ammonium chloride, di-n-octyl dimethyl ammonium chloride, dodecyl dimethyl ammonium chloride, n-alkyl dimethyl benzyl ammonium saccharinate, and 3-(trimethoxysilyl) propyldimethyloctadecyl ammonium chloride.
  • QAC combination is N-alkyl dimethyl benzyl ammonium chloride (40%)); N-octyl decyl dimethyl ammonium chloride (30%>); di-n-decyl dimethyl ammonium chloride (15%); and di-n-dioctyl dimethyl ammonium chloride (15%).
  • the percentage is the weight percentage of individual QAC based on the total weight of blended QACs composition.
  • Ri, R 2 , R5, and R5, independently, include, but are not limited to, hydrogen, methyl, ethyl, propyl or other longer carbon alkyl groups.
  • R3 and R 4 are independently selected and include, but are not limited to, methylene, ethylene, propylene or other longer alkylene linking groups.
  • n is the degree of polymerization; n is an integer in a range of from 2 to 10,000.
  • cationic polymers with the above structure include but are not limited to, polyamines derived from dimethylamine and epichlorohydrin such as Superfloc C-572 commercially available from Kemira Chemicals.
  • Still another polymeric QAC suitable for the invention is poly diallyldimethylammonium chloride or polyDADMAC.
  • QACs useful for the present invention are those chemical compounds with biguanide moiety in the molecule. Examples of this class of cationic antimicrobials include, but are not limited to, PHMB and chlorhexidine.
  • Examples of commercially available quaternary ammonium compounds include, but are not limited to, Bardac 205M and 208M from Lonza, and BTC885 from Stepan Company.
  • the biocidal compound may be a weak acid, which has been shown to be particularly effective in bathroom cleaners.
  • citric, sulfamic also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, and sulfamidic acid
  • glycolic, lactic, lauric and capric acids are useful as both an effective biocide and a cleaning agent for soap scum and hard wart deposits.
  • silane quaternary salts such as 3(trihydroxysilyl)propyldimethyloctadecyl ammonium chloride. These may have the added benefit of reacting to the surface being treated for an enhancement of the residual properties.
  • biocidal compounds suitable for use in the present liquid formulation span a broad range of antimicrobials, biocides, sanitizers, and disinfectants.
  • a water soluble or dispersible biocidal compound is preferred, although biocides soluble in alcohol may be alternatively employed.
  • biocidal compounds suitable for use in the present formulation include triclosan, zinc pyrithione, metal salts and oxides, phenols, botanicals, halogens, peroxides, heterocyclic antimicrobials, aldehydes, and alcohols.
  • the concentration of biocidal compound in the formulation can be in a range of 0.05% to 20%) based on the weight of the liquid composition.
  • a liquid formulation for a healthcare application preferably in a range of 0.1%> to 20%, and more preferably in a range of 0.5% to 3%.
  • a liquid formulation for all-purpose and bathroom cleaners preferably in a range of 0.05% to 10%.
  • a formulation for a protectant preferably in a range of 0.05% to 2%.
  • the carrier or media for the liquid formulation of this invention can be any solvent that is volatile and allow easy evaporation at ambient condition.
  • liquid carriers include, but are not limited to, water and low molecular weight alcohols such as CI to C8 alkanols. Specific examples include, but are not limited to, ethanol, isopropyl alcohol, butanol, pentanol, and combinations thereof.
  • alkylene glycol ether examples include, but are not limited to, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, ethylene clycol monohexyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monobutyl ether, propylene glycol methyl ether, propylene glycol methyl ether acetate, propylene glycol n- butyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol methyl ether acetate, propylene glycol n-propyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n
  • solvents for use in the invention is based on terpenes and their derivatives such as terpene alcohols, terpene esters, terpene ethers, or terpene aldehydes.
  • terpene alcohols such as pine oil, lemon oil, limonene, pinene, cymene, myrcene, fenchone, borneol, nopol, cineole, ionone and the like.
  • a preferred carrier in a liquid formulation for a home care cleaning application is water.
  • a propellant may be needed in the composition.
  • a variety of propellants or mixtures can be used for the present invention and should be familiar to those skilled in the art.
  • CI to CIO hydrocarbons or halogenated hydrocarbons are typical propellants in aerosol compositions known to the industry.
  • Examples of such propellants include, but are not limited to, pentane, butane, propane, and methane.
  • Other types of propellants that can be used for the present invention also include compressed air, nitrogen, or carbon dioxide.
  • a bag on valve package may be used to aerosol the product without directly add a propellant to the composition.
  • Either a single solvent or a mixture of the above solvents can be used for the present invention.
  • the types of solvents used for the present invention may depend upon the intended uses of the residual disinfectant composition. For example, if the composition of the present invent is intended for home care use, cleaning the contaminated surfaces free of all types of dirt or soil may be of primary interest. Liquid carrier or media that assist and enhance the removal of soil may be formulation of the invention.
  • the residual disinfectant formulation or composition of the present invention may desire to include alkyl or multi-alkyl glycol ethers for better cleaning performance in the home care version of the formulation of the present invention.
  • the primary goal of the residual disinfectant composition is to be used at a health care facility where the major concern is hospital acquired infection, then quick drying of the liquid composition of the present invention may be more desirable than cleaning dirt or soil out of the surfaces.
  • Low molecular weight alcohols should be considered to help the liquid formulation of the present invent dry fast after the application. Also, a low molecular weight alcohol in the liquid formulation will strengthen the sanitizing activity of the liquid composition.
  • a mixture of water and low molecular weight alcohol is preferred.
  • the amount of alcohol present in the liquid formulation is preferred to be at such a level that the liquid formulation is capable of forming a zerotropic mixture between the alcohol and water.
  • a minimum amount of alcohol, if present, in the liquid composition is 10%.
  • the alcohol concentration is 30%, and most preferably the alcohol concentration is at least 50% based on the weight of liquid formulation for the health care use of the composition of the invention.
  • a surfactant or wetting agent may be employed.
  • the surfactant assists the liquid formulation to spread and evenly coat the surface being treated.
  • the surfactant additionally contributes to the formation of a zeotropic mixture between alcohol and water, thus facilitating a rapid and uniform drying of the liquid formulation once being applied onto surface.
  • a surfactant also plays an important role in the residual disinfectant liquid formulation of the present invention for home care use if the soil cleaning performance is the key feature the product is designed to possess.
  • Surfactants appropriate for the present liquid formulation include, but are not limited to, those that are nonionic, anionic, or amphoteric in nature.
  • Examples of commercially available wetting agents include, but are not limited to, Ecosurf SA-4 or Tergitol TMN-3 from Dow Chemical, and Q2-521 1 from Dow Corning.
  • An amine oxide surfactant is preferred especially when the QAC is used as the biocidal compound in the formulation.
  • ethoxylated alcohols with different amounts of ethylene oxides or HLB values can be used.
  • ethoxylated alcohols include, but are not limited to, Triton X-100 (Dow Chemical, Midland MI), Ecosurf EH nonionic surfactant series from Dow Chemical, Tergitol nonionic surfactant series from Dow Chemical, the Sulfonic surfactant series from Huntsman Corp., the Neodol surfactant series from Shell, the Ethox surfactant series from Ethox Chemicals and the Tomadol surfactant series from Air Products and Chemicals, Inc.
  • nonionic surfactants include alkylpolyglucosides. Examples include the Glucopon Series from BASF and the Ecoteric series from Huntsman.
  • silane-based surfactants examples include but, are not limited to, silicone polyethers organofunctional or reactive silane wetting agents, and fluorochemical based wetting agents.
  • the content of the surfactant in the liquid formulation is in a range of 0% to 10%, preferably in a range of 0.01% to 5%.
  • a liquid formulation of the present invention for home care use may need appropriate pH condition.
  • a high pH product may be desired in order to effectively remove grease soils commonly found in the area.
  • soap scum and hard water deposits may be the primary concern.
  • a low pH product may be more appropriate for such a purpose.
  • Example of pH adjusting agents that can be used include, but are not limited to, triethanolamine, diethanolamine, monoethanolamine, sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate, calcium carbonate, citric acid, acetic acid, hydrochloric acid, sulfamic acid, sulfuric acid and the like.
  • Additional functional components may be included in the liquid composition of the present invention. Additional components include, but are not limited to, chelants, compatibilizers, coupling agents, corrosion inhibitors, rheology modifiers, fragrances, colorants, preservatives, UV stabilizers, optical brighteners, and active ingredient indicators.
  • the liquid solution comprises a polymer binder, a quaternary ammonium compound, a silicone-based surfactant, and ethanol.
  • the liquid formulation can be made or mixed by any conventional method known to one of ordinary skill in the art. There are no preferred addition procedures for the formulation of the present invention provided that the formulation is ultimately homogeneous, compatible and stable. For example, if the polymer binder is a solid, it may be preferable to first dissolve or disperse the polymer in a carrier such as water or alcohol to make a stock polymer binder liquid dispersion. The stock polymer binder liquid dispersion may be readily added into the formulation of the present invention during the mixing procedure.
  • the liquid formulation may be applied by a variety of means. If sprayed, the liquid formulation advantageously may be supplied in a conventional bottle with a sprayer.
  • the sprayer can be a trigger sprayer.
  • an aerosol can also be used to deliver the liquid formulation on to surfaces. Additional application means include, but are not limited to, fogging, rolling, brushing, mopping, and using a wipe by a variety of application devices. It is within the scope of the present invention that wipe products can also be made comprising or pre-treated with the disinfectant formulation(s) of the present invention, for example, for off-the-shelf sale or use.
  • a wipe having up to 24-hour residual sanitization activity.
  • the wipe is capable of protecting a hard surface from microbial growth and protection against bacteria without leaving a significant residue or build-up.
  • the wipe is comprised of a substrate and a formulation applied on the substrate or present in the substrate of the wipe.
  • the wipe formulation provides a solid transparent film water soluble enough to be easily removed with additional cleanings yet durable enough to remain on the surface even after being touched.
  • the substrate is any fibrous material capable of absorbing and/or adsorbing water, preferably at least three times its weight in water.
  • the substrate comprises a synthetic material, a natural material, or a combination thereof.
  • synthetic materials include, but are not limited to, polypropylene, polystyrene, polyester, nylon, rayon, acrylic, spandex, and a combination thereof.
  • natural materials include, but are not limited to, cotton, linen, silk, wool, hemp, flax, and a combination thereof.
  • the substrate may be woven or non-woven.
  • a non-woven substrate may be made by any number of manufacturing methods.
  • the resulting non-woven substrate may be, but is not limited to, melt-blown, coformed, spunbonded, airlaid, hydroentangled, spunlaced, bonded, carded, laminated, or a combination thereof.
  • a substrate may comprise a melt-blown polymeric material.
  • the wipe formulation comprises a biocidal compound, a polymer binder and a wetting agent/surfactant.
  • the wipe formulation may comprise a cationic containing compound that is designed to compete with the quaternary ammonium compound(s) for anionic species sites on the substrate. Salts with high ionic strengths can also be used. Examples of salts for use in the wipe formulation include, but are not limited to, potassium citrate, sodium citrate, magnesium sulphate, sodium chloride, ammonium chloride, potassium chloride, and a combination thereof.
  • the wipe formulation provides initial disinfection then once dried leaves a residual protective film on the surface. The film possesses biocidal properties with the ability to kill bacteria, for example, within a 5-minute contact time for up to 24 hours after initial application.
  • the wipe formulation comprises a poly(2-ethyl-2- oxazoline), a quaternary ammonium compound or combination of quaternary ammonium compounds, an alcohol ethoxylate, water, and an optional fragrance.
  • Quaternary ammonium compounds are especially suited for this wipe application as they provide protection against a broad range of microorganisms. Examples of such compounds are commercially available from Stepan Chemical under the trade name BTC885. BTC885 contains 50% of a blend of quaternary ammonium compounds. A similar material is also commercially available from Lonza under the trade name Bardac 205M.
  • the quaternary ammonium compound and the binder are in a ratio of quaternary ammonium compound to binder of 1 :4 to 1 : 1.
  • the wipe formulation comprises a poly(2-ethyl-2-oxazoline) in an amount of 1 weight % to 5 weight %, wherein the weight percentage is based on the total weight of the wipe formulation.
  • the wipe formulation comprises a quaternary ammonium compound in an amount of at least 0.2 weight percent, preferably 0.2 weight percent to 2 weight percent, wherein the weight percentage is based on the total weight of the wipe formulation.
  • the wipe formulation comprises a nonionic surfactant.
  • the nonionic surfactant is an alcohol ethoxylate.
  • the wipe formulation comprises the alcohol ethoxylate in an amount of 0.05 weight % to 0.5 weight %, wherein the weight percentage is based on the total weight of the wipe formulation.
  • a preferred alcohol ethoxylate is a linear alcohol ethoxylate with at least 9 moles of ethylene oxide, more preferably with at least 12 moles of ethylene oxide.
  • an alcohol ethoxylate such as in this group, when used in the formulation of the present invention surprisingly and favorably contributes to the aesthetics of the resulting film by drying to a hard transparent film (as opposed to a tacky, hazy film) yet remains water soluble enough to allow release of the quaternary ammonium compound(s) for antimicrobial efficacy.
  • a weak acid including, but not limited to, citric acid, lactic acid, sulfamic, acid, gly colic acid, or a combination thereof can be added to the formulation to increase efficacy against gram negative bacteria and aid in hard water stain or soap scum soil removal.
  • Ethylenediaminetetraacetic acid, disodium salt or EDTA disodium salt can be added to the formulation to increase antimicrobial efficacy in the presence of hard water.
  • the wipe formulation optionally comprises a fragrance. If a fragrance is present, the wipe formulation preferably comprises a fragrance in an amount of 0 weight % to 0.5 weight %, wherein the weight percentage is based on the total weight of the wipe formulation.
  • Water is a suitable carrier for inert and active materials. Solvents such as ethanol or isopropanol are optionally added to decrease drying time.
  • the wipe formulation of the present invention is effective for the above purposes without requiring other components to be present in the formulation, although other components may be present.
  • the wipe formulation of the present invention is effective for its residual sanitization activity without hydrogen peroxide as a component of the formulation.
  • To disinfect a contaminated surface spray the liquid formulation until the area is completely covered.
  • the wet formulation subsequently may be wiped dry with a dry cloth or paper towel.
  • the invention also relates to an article treated with a disinfectant formulation in accordance with aspects of the invention.
  • Formulations were tested for residual efficacy using the EPA 01-1 A protocol. Briefly, bacteria were added to a glass slide and allowed to dry on the surface. The formulation was then sprayed onto the surface and dried to form a transparent film. Once a film had formed, the glass slide was exposed to alternating wet and dry cycles using the Gardner wear tester as described in the protocol. In between each cycle the slide was re- inoculated with bacteria. After the appropriate number of wear and re-inoculations (48 passes and 11 re-inoculations for healthcare formulation and 24 passes 5 re-inoculation for homecare formulation) the slide was exposed to bacteria for the indicated time frame (i.e. 5 minutes) followed by recovery in an appropriate neutralizing solution.
  • the indicated time frame i.e. 5 minutes
  • initial efficacy of the composition of the present invention was also tested according to ASTM E 1153.
  • a modified ASTM D4488 was used to evaluate the hard surface cleaning performance for the home care composition of the present invention.
  • a soil of the following composition was used for the evaluation. Table 1
  • a Gardner wear tester was used in the cleaning test. Scouring pads of around 1 cm width were attached to the abrasion boat for the wearing. Around 4 grams of test formulation was placed in a weighing boat. The attached scouring pad was dipped into the weighing boat to pick up the testing formulation.
  • the cleaning process started immediately after the pad is wetted with the cleaning formulation. Seven wearing cycles (back and forth) were used in the test.
  • the following formulation in the example uses alcohol as the major carrier in order to provide fast drying property to the liquid formulations.
  • compositions are formulated using water as the carrier. They are intended for homecare use where VOC regulations prohibit most use of high levels of organic solvents such as alcohols.
  • Enterobacter aerogenes was the bacterial for HI testing and Staphylococcus aureus was the bacteria used in the testing for the rest of the formulations.
  • the testing results demonstrate that the HI to H5 all provide residual efficacy to the treated surfaces.
  • the cleaning performance was also evaluated using the modified ASTM D4488 test method.
  • a concentrate of a water based formulation is prepared by removing a portion of the water from the formulation, concentrating the remaining raw materials. The resulting concentrate can then be diluted back to use strength prior to use.
  • the 5 times and 10 times concentrates are typically used in the janitorial and sanitization supply industries with customers in the hospitality area. Concentrates can be prepared at 15 times, 20 times, or even higher levels, as desired, and still be within the scope of the present invention. Concentrates are desirable in these industries as it reduces shipping costs and conserves storage space.
  • Table 10 illustrates example concentrate formulations in an embodiment of the invention.
  • Wipe formulations A-I were prepared and tested on various substrates.
  • Clorox method 01-1 A results - The method was adapted to wipes by folding the substrate lengthwise into 1" folds then wrapping the folded substrate strip across the second, third and fourth fingers. One pass was made across the glass carriers. A log reduction greater than 3.0 was required to be considered passing.
  • Clorox method 01-1 A results - The method was adapted to wipes by folding the substrate lengthwise into 1" folds then wrapping the folded substrate strip across the second, third and fourth fingers. One pass was made across the glass carriers. A log reduction greater than 3.0 was required to be considered passing.
  • Clorox method 01-1 A results - The method was adapted to wipes by folding the substrate lengthwise into 1" folds then wrapping the folded substrate strip across the second, third and fourth fingers. One pass was made across the glass carriers. A log reduction greater than 3.0 was required to be considered passing.

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Abstract

L'invention concerne une formulation désinfectante comprenant une poly(2-éthyl-2-oxazoline) et un composé d'ammonium quaternaire ou une combinaison de composés d'ammonium quaternaire. L'invention concerne également une lingette ayant une propriété biocide résiduelle. La formulation de lingette comprend un substrat constitué d'un matériau fibreux, et la formulation présente sur le substrat ou dans ce dernier. La formulation comprend une poly(2-éthyl-2-oxazoline), un composé d'ammonium quaternaire ou une combinaison de composés d'ammonium quaternaire, un tensioactif, de l'eau et un parfum facultatif.
PCT/US2018/037354 2017-06-16 2018-06-13 Désinfectant de surface ayant une propriété biocide résiduelle WO2018232000A1 (fr)

Priority Applications (7)

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JP2019565448A JP2020523293A (ja) 2017-06-16 2018-06-13 残留殺菌特性を有する表面殺菌剤
RU2020101126A RU2020101126A (ru) 2017-06-16 2018-06-13 Поверхностное дезинфицирующее вещество с остаточным биоцидным свойством
MX2019015269A MX2019015269A (es) 2017-06-16 2018-06-13 Desinfectante de superficies con una propiedad biocida residual.
CN201880039705.0A CN110868858A (zh) 2017-06-16 2018-06-13 具有残留杀生物性质的表面消毒剂
CA3063749A CA3063749A1 (fr) 2017-06-16 2018-06-13 Desinfectant de surface ayant une propriete biocide residuelle
BR112019026250-4A BR112019026250A2 (pt) 2017-06-16 2018-06-13 Pano de limpeza tendo uma propriedade biocida residual, e, formulação desinfetante.
EP18818125.9A EP3638027A4 (fr) 2017-06-16 2018-06-13 Désinfectant de surface ayant une propriété biocide résiduelle

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US15/625,612 US10925281B2 (en) 2014-11-26 2017-06-16 Surface disinfectant with residual biocidal property

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JP2020523293A (ja) 2020-08-06
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CA3063749A1 (fr) 2018-12-20
CL2019003584A1 (es) 2020-10-23
CN110868858A (zh) 2020-03-06
RU2020101126A3 (fr) 2021-09-06
EP3638027A4 (fr) 2021-03-17
BR112019026250A2 (pt) 2020-06-23
EP3638027A1 (fr) 2020-04-22

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