WO2020023645A1 - Compositions antimicrobiennes de sulfonamide aromatique halo-actif - Google Patents

Compositions antimicrobiennes de sulfonamide aromatique halo-actif Download PDF

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Publication number
WO2020023645A1
WO2020023645A1 PCT/US2019/043256 US2019043256W WO2020023645A1 WO 2020023645 A1 WO2020023645 A1 WO 2020023645A1 US 2019043256 W US2019043256 W US 2019043256W WO 2020023645 A1 WO2020023645 A1 WO 2020023645A1
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Prior art keywords
substituted
unsubstituted
composition
alkyl
hydrogen
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PCT/US2019/043256
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English (en)
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David J. Schneider
Jonathan Schneider
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Rem Brands Inc.
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Priority to EP19749991.6A priority Critical patent/EP3826465A1/fr
Priority to CA3102998A priority patent/CA3102998A1/fr
Publication of WO2020023645A1 publication Critical patent/WO2020023645A1/fr

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    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65F—GATHERING OR REMOVAL OF DOMESTIC OR LIKE REFUSE
    • B65F1/00—Refuse receptacles; Accessories therefor
    • B65F1/14—Other constructional features; Accessories
    • B65F1/141—Supports, racks, stands, posts or the like for holding refuse receptacles
    • B65F1/1415—Supports, racks, stands, posts or the like for holding refuse receptacles for flexible receptables, e.g. bags, sacks

Definitions

  • the present disclosure relates to disinfecting compositions and processes utilizing the same that can obtain extended microbial killing performance and prophylactic protection over a long period of time (multiple days).
  • the antimicrobial compositions are particularly effective in residual, dry-coated, form.
  • the compositions and associated processes find particular usefulness in settings and environments wherein constant exposure to bacteria and other microorganisms which may cause infection or sickness.
  • HAI hospital acquired infection
  • Medicare may not reimburse the hospital for the costs of the readmittance. Therefore, the hospital must absorb 100% of the cost associated with treatment of the patient until s/he is well again.
  • the estimated annual cost in the United States for HAI's is in the billions of dollars.
  • HAIs such as bacterial infections are significant causes of disease and death in the general community and in health-care settings.
  • Vaccines to prevent many bacterial infections are not currently available.
  • the ability to treat bacterial infections with antibiotics is threatened by widespread drug-resistance and the emergence of “super bugs” that are resistant to most currently licensed antibiotics.
  • Effective methods for destroying living bacteria and bacterial endospores are needed to limit the infection of new hosts.
  • bacteria such as Staphylococcus aureus, Pseudomonas aeruginosa, and Clostridium difficile are responsible for hundreds of thousands of new infections each year in the U.S. They cause thousands of deaths each year, and cost hundreds of millions of dollars annually in health care expenses.
  • halo active aromatic sulfonamide compositions can provide extended microorganism killing performance on various surfaces to which they are applied. These compositions are particularly effective in evaporated dry-coated or coating applications. In certain circumstances, such residual kill performance can extend for up to one week (seven days, 168 hours), or even two weeks (14 days, 336 hours) or more.
  • the halo active aromatic sulfonamide compositions are not orally toxic, contact sensitive and/or irritating to the skin, and they do not irritate the eyes.
  • FIGS. 1A-1 F are graphs showing the ATP count on different surfaces over time after application of a certain embodiment of a disinfecting composition of the present disclosure.
  • the y-axis is the ATP count.
  • the x-axis indicates the time measurement.
  • FIG. 1 A is a graph illustrating application on a bedside TV remote control. The y-axis runs from 0 to 5000 in increments of 1000.
  • FIG. 1 B is a graph illustrating application on a children’s play table in a waiting room.
  • the y-axis runs from 0 to 8000 in increments of 2000.
  • FIG. 1C is a graph illustrating application on a patient toilet.
  • the y-axis runs from 0 to 15000 in increments of 5000.
  • FIG. 1 D is a graph illustrating application on a hospital wheelchair armrest.
  • the y-axis runs from 0 to 8000 in increments of 2000.
  • FIG. 1 E is a graph illustrating application on an administration stairway handrail.
  • the y-axis runs from 0 to 6000 in increments of 2000.
  • FIG. 1 F is a graph illustrating application on a men’s toilet flush handle.
  • the y-axis runs from 0 to 5000 in increments of 1000.
  • FIG. 2 is a graph showing the effect of 24-hour exposure of a dry-coated disinfecting composition on S. aureus in accordance with one aspect of the present disclosure.
  • FIG. 3 is a graph showing the effect of 14-day exposure of a dry-coated disinfecting composition on S. aureus in accordance with another aspect of the present disclosure.
  • FIG. 4 is a graph showing the effect of a 14-day exposure of a dry-coated disinfecting composition on P. aeruginosa in accordance with a further aspect of the present disclosure.
  • FIGS. 5A-5C are graphs showing the effect of a dry-coated disinfecting composition on three strains of C. difficile in accordance with still another aspect of the present disclosure.
  • FIG. 6A is a perspective view of a conventional trash bag on which a dry disinfectant coating can be formed.
  • FIG. 6B is a cross-sectional view of a sidewall of the trash bag of FIG. 6A.
  • the term “comprising” may include the embodiments “consisting of” and “consisting essentially of.”
  • the terms “comprise(s),”“include(s),”“having,”“has,”“can,”“contain(s),” and variants thereof, as used herein, are intended to be open-ended transitional phrases, terms, or words that require the presence of the named ingredients/steps and permit the presence of other ingredients/steps.
  • compositions or processes as “consisting of” and “consisting essentially of” the enumerated ingredients/steps, which allows the presence of only the named ingredients/steps, along with any impurities that might result therefrom, and excludes other ingredients/steps.
  • ambient temperature refers to a temperature of 20°C to 25°C.
  • alkyl refers to a radical composed entirely of carbon atoms and hydrogen atoms which is fully saturated.
  • the alkyl radical may be linear, branched, or cyclic, and such radicals may be referred to as linear alkyl, branched alkyl, or cycloalkyl.
  • aromatic refers to a radical that has a ring system containing a delocalized conjugated pi system with a number of pi-electrons that obeys Fltickel’s Rule.
  • the ring system may include heteroatoms (e.g. N, S, Se, Si, O), or may be composed exclusively of carbon and hydrogen.
  • exemplary aromatic groups include phenyl, thienyl, naphthyl, and biphenyl.
  • aryl refers to an aromatic radical composed exclusively of carbon and hydrogen.
  • exemplary aryl groups include phenyl, naphthyl, and biphenyl.
  • heteroaryl refers to an aromatic radical containing at least one heteroatom.
  • exemplary heteroaryl groups include thienyl. Note that“heteroaryl” is a subset of“aromatic”, and is exclusive of“aryl”.
  • alkoxy refers to an alkyl radical which is attached to an oxygen atom, i.e. -0-CnFl2n+i , to a molecule containing such a radical.
  • halogen refers to fluorine, chlorine, bromine, and iodine.
  • substituted refers to at least one hydrogen atom on the named radical being substituted with another functional group, such as halogen, -CN, or -NO2. Besides the aforementioned functional groups, an aromatic group may also be substituted with alkyl or alkoxy. An exemplary substituted aryl group is methylphenyl.
  • alkali metal refers to lithium, sodium, and potassium.
  • alkaline earth metal refers to magnesium and calcium.
  • antimicrobial means an agent that will kill or inhibit the growth of microorganisms, such as, for example, bacteria, viruses, and fungi.
  • fect means to inactivate, kill, or otherwise render non-pathogenic a pathogen, such as, for example, a bacteria, virus, for fungus.
  • killing performance refers to the ability of a composition to inactivate, kill, or otherwise render non-pathogenic a microorganism, and may be measured as a function of the reduction in viability of a particular microorganism.
  • the term “killing performance” may also have a time/duration dimension (i.e. killing performance at 24 hours, 48 hours, 72 hours, etc.).
  • film or layer or“coating” refers to a covering upon the surface of an object (also called a substrate).
  • the film or layer or coating may cover the entire surface, or just a portion of the surface.
  • dry is used to refer to the film or layer or coating containing so little solvent that it does not flow when in the steady state.
  • gel refers to the film or layer or coating being cross-linked and not flowing when in the steady state.
  • Staphylococcus aureus i.e. S. aureus
  • S. aureus is a gram-positive bacteria commonly found on skin and in the nasopharynx. It can infect any human tissue, invade the body, and cause death. It is a leading cause of bacterial infections and death due to bacterial infections.
  • Antibiotic treatment of S. aureus infection is complicated by widespread drug- resistance (MRSA, VRSA).
  • Pseudomonas aeruginosa i.e. P. aeruginosa
  • P. aeruginosa is a gram-negative bacteria found throughout the natural and health care environment. It can infect any human tissue, invade the body, and cause death. It is a leading cause of bacterial infections and death in the immunocompromised, especially in cancer and burn patients. Antibiotic treatment of P. aeruginosa infection is complicated by widespread drug-resistance.
  • Clostridium difficile i.e. C. difficile
  • C. difficile is a spore-forming gram-positive bacteria that is highly prevalent in the environment. It is a common cause of antibiotic-associated diarrhea and may cause life-threatening infections. The spores of C. difficile survive long-term in the environment and contaminate many surfaces in hospital environments. C. difficile is anaerobic, grows only where there is no oxygen, and cannot survive outside the body as a living cell, therefore it forms bacterial endospores. C. difficile endospores are highly resistant to disinfectants and various forms of radiation, and can persist for years on surfaces. Antibiotic treatments for C. difficile infection are complicated by endospore formation in the body, as the dormant endospores are not affected by antibiotics. Effective methods for destroying bacterial endospores need to be developed to limit the infection of new hosts.
  • Halo active aromatic sulfonamide organic compounds have been known to reduce or eliminate odor.
  • Chloramine-T is an example of a sulfonamide organic compound which has been used in many applications. The usefulness of Chloramine-T is predicated on its ability to release an active chloride ion when needed on demand, immediately after which it simultaneously generates an active aromatic sulfo nitrene companion ion.
  • the chlorine atom has a +1 formal charge in a hypochlorite ion, CIO , which is the form taken by the chlorine atom when dissociated from the sulfonamide compound.
  • Reference to the chlorine atom as having a +1 or T charge may be used in this application interchangeably because this terminology has no effect on the compound itself or its use.
  • halo active aromatic sulfonamide organic compounds also have an antimicrobial performance that can extend over long periods of time, particularly in residual, or dry-coated, form. This may be useful in any setting where large numbers of people congregate, particularly sick people. This can include commercial, industrial, governmental, and other institutional facilities, including places such as a hospital, nursing home or long term care facility, school, jail or prison, an airport, a vehicle, a watercraft, an airplane, a house, a gym or workout facility, or a supermarket.
  • the disinfectant ability may be maintained for at least 1 month, at least 2 months, at least 3 months, at least 4 months, at least 5 months, at least 6 months, at least 7 months, at least 8 months, at least 9 months, at least 10 months, at least 1 1 months, or at least 12 months, or more.
  • halo active aromatic sulfonamide organic compounds also have several usage benefits over traditional disinfectants such as bleach or hydrogen peroxide.
  • bleach has a very strong chlorine odor in open air and during cleaning; is rapidly destructive for many surface types; only reduces microbes when wet, and has essentially no residual antimicrobial action once dry; has poor stability in“non-ambient” temperatures and light exposure; and is toxic, a skin and eye irritant, and a skin sensitizer.
  • compositions using halo active aromatic sulfonamide organic compounds can have equivalent antimicrobial performance, but also have long term residual antimicrobial action when dried on a surface; offer residual odor elimination when dry; have excellent stability, with a shelf life measured in years; and have extremely low toxicity, are not skin/eye irritating, and are not a sensitizer.
  • the disinfecting compositions of the present disclosure comprise (A) a halo active aromatic sulfonamide compound, as described further herein.
  • the compositions can also include (B) water; (C) a buffering agent; (D) a surfactant; (E) a tracer fragrance; and/or (F) alcohol, in any combination, and preferably, of two or more of these additional ingredients.
  • the disinfecting / antimicrobial compositions may be evaporative, meaning that a portion of the composition evaporates to leave a residual antimicrobial / disinfecting coating (i.e. a dry-coated film) that can maintain a suitable killing performance for extended periods of time.
  • halo active aromatic sulfonamide compound used in the disinfecting compositions of the present disclosure has the structure of base Formula (I): n H O
  • Ri, R2, R3, R4, and Rs are independently selected from hydrogen, COOR’, CON(R”)2, alkoxy, CN, NO2, SO3R”, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, N(R”)2, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted aromatic;
  • R’ is hydrogen, an alkali metal, an alkaline earth metal, substituted C1-C12 alkyl, or unsubstituted C1-C12 alkyl;
  • R is hydrogen or substituted or unsubstituted C1-C12 alkyl, where the two R” groups in CON(R”)2 and N(R”)2 may be independently selected;
  • X is halogen
  • M is an alkali or alkaline earth metal
  • n is the number of water molecules per molecule of the sulfonamide compound.
  • M is sodium or potassium.
  • X is generally chlorine, bromine, fluorine, or iodine, and in particular embodiments is chlorine.
  • Compounds of Formula (I) may or may not be hydrated, as indicated by the variable n.
  • the compound is in a solid form, such as a powder.
  • R3 is methyl, COOH, or COOM1 ;
  • R-i, R2, R4, and R5 are independently selected from hydrogen, COOH, COOM1, COOR’, CON(R”)2, alkoxy, CN, NO2, SO3R”, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, N(R”)2, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted aromatic;
  • X is halogen;
  • Mi is an alkali or alkaline earth metal; and
  • n is the number of water molecules per molecule of the sulfonamide compound.
  • R3 is methyl, COOH, or COOM1 ;
  • R1, R2, R4, and Rs are independently selected from hydrogen, COOH, COOM1, COOR’, CON(R”)2, alkoxy, CN, NO2, SO3R”, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, N(R”)2, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted aromatic;
  • X is halogen;
  • M is an alkali or alkaline earth metal;
  • n is the number of water molecules per molecule of the sulfonamide compound; and at least one of R1, R2, R4, and Rs is not hydrogen.
  • R3 is selected from COOH, COOM1, COOR’, CON(R”)2, CN, NO2, halogen, and substituted or unsubstituted C2-C12 alkyl;
  • R1, R2, R4, and Rs are independently selected from hydrogen, COOH, COOM1, COOR’, CON(R”)2, alkoxy, CN, NO2, SO3R”, halogen, substituted or unsubstituted phenyl, sulfonamide, halosulfonamide, N(R”)2, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted aromatic;
  • X is halogen;
  • M is an alkali or alkaline earth metal; and
  • n is the number of water molecules per molecule of the sulfonamide compound.
  • R1, R2, R3, R4, and Rs are independently selected from hydrogen, COOH, COOM1, NO2, halogen, N(R”)2, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted aromatic;
  • X is halogen;
  • M is an alkali or alkaline earth metal; and
  • n is the number of water molecules per molecule of the sulfonamide compound.
  • R2 and R4 are identical to each other; and R1 , R3, and Rs are hydrogen.
  • R2 and R4 are hydrogen; and R1, R3, and Rs are identical to each other.
  • R3 is selected from COOH, COOM1, COOR’, and CON(R”)2. Most desirably, R3 is COOH or COOM1, while R-i, R2, R 4 , and R5 are hydrogen.
  • R-i, R2, R3, R4, and Rs are independently selected from hydrogen, COOH, COOM1, COOR’, CON(R”) 2 , NO2, halogen, N(R”) 2 , substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted aromatic; wherein at least one of R1, R2, R3, R4, and Rs is not hydrogen; X is halogen; M is an alkali or alkaline earth metal; and n is the number of water molecules per molecule of the sulfonamide compound.
  • R3 is COOH or COOM1;
  • R1, R2, R4, and Rs are independently selected from hydrogen, NO2, halogen, N(R”)2, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted aromatic;
  • X is halogen;
  • M is an alkali or alkaline earth metal; and
  • n is the number of water molecules per molecule of the sulfonamide compound.
  • at least one of R1, R2, R4, and Rs is not hydrogen.
  • At least one of R1, R2, R3, R4, or Rs are not hydrogen. In more specific embodiments of Formula (I), at least two of R1, R2, R3, R4, or Rs are not hydrogen.
  • the benzene ring contains the sulfonamide substituent and an additional one or two other substituents.
  • the halo active aromatic sulfonamide compound has the structure of Formula (II):
  • R3 is COOR’
  • R’ is hydrogen, an alkali metal, an alkaline earth metal, substituted C1-C12 alkyl, unsubstituted C1-C12 alkyl, substituted aromatic, or unsubstituted aromatic
  • X is halogen
  • M is an alkali or alkaline earth metal
  • n is the number of water molecules per molecule of the sulfonamide compound.
  • the N-chloro-4- carboxybenzenesulfonamide compound of Formula (II) is also referred to herein as BENZ.
  • BENZ exhibits a lower chlorine smell than chloramine-T or chloramine-B. When BENZ is combined with at least one fragrance, there is no detectable chlorine smell for most humans.
  • N-chloro-p- toluenesulfonamide i.e. chloramine-T
  • N-chloro-4-carboxybenzenesulfonamide i.e. BENZ
  • Formula (III) Formula (IV) wherein M2 is hydrogen, an alkali metal, or an alkali earth metal; X is halogen, M is independently an alkali or alkaline earth metal; and n is the number of water molecules per molecule of each sulfonamide compound. Desirably, M2 is hydrogen, sodium, or potassium.
  • R1, R2, R3, R4, and Rs are substituted with -COOR’ (and the others are hydrogen).
  • -COOR a halo active aromatic sulfonamide compound
  • the compound has higher antimicrobial performance.
  • the antimicrobial performance of these compounds of Formula (I) was not expected, because sulfonamide groups having a halogen atom bonded to the nitrogen atom are not present in molecules having known antimicrobial properties.
  • the halo active aromatic sulfonamide compounds of base Formula (I) are stable and do not decompose in aqueous solution, allowing the disinfecting composition to have a long shelf life.
  • the compounds of Formula (I) are also very soluble in water, low in toxicity, and have minimal bleach odor.
  • the halo active aromatic sulfonamide compound (A) is generally present in the disinfecting composition in the amount of about 0.0001 wt% to about 5 wt%.
  • the halo active aromatic sulfonamide compound (A) may be up to about 100 wt% of the dry material, including from about 0.0001 wt% to nearly about 100 wt% of the dry material.
  • the pH of the disinfecting composition should be between 5 and 14, though generally the pH should be kept between 8 and 14, or between 6 and 10, or between 6.5 and 9, or between 7 and 9, or between 7 and 8.5, or between 8 and 9.
  • a buffering agent (C) can be included to maintain the solution within these pH ranges.
  • Exemplary buffering agents include sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, acetate buffers (such as sodium acetate), phosphate buffers (such as tri and di sodium phosphate and mixtures thereof, pH blended phosphates, sulfate buffers (such as di and tri sodium sulfate), and mixtures thereof.
  • the buffering agent can be added up to the limit of solubility in the disinfecting compositions.
  • the preferred weight ratio of the sulfonamide compound to the buffering agent is from about 1000: 1 to about 1 : 1 , or from about 500: 1 to about 2: 1 , or from about 100: 1 to about 2: 1 , or from about 50: 1 to about 1 : 1 , or from about 50: 1 to about 2: 1 , or from about 20: 1 to about 2: 1 .
  • the preferred buffering agent is sodium bicarbonate.
  • the disinfecting composition can comprise from about 0.01 wt% to about 2 wt% of the halo active aromatic sulfonamide compound (A), or from about 0.1 wt% to about 1 wt% of the halo active aromatic sulfonamide compound (A).
  • the disinfecting composition can comprise a buffering agent (C) and have a pH of from about 6.5 to about 9, or from about 7 to about 8.5.
  • the residual dry-coat formed from the disinfecting composition can comprise at least 5 wt% of the halo active aromatic sulfonamide compound (A), or at least 10 wt% of the halo active aromatic sulfonamide compound (A), or at least 25 wt% of the halo active aromatic sulfonamide compound (A), or at least 50 wt% of the halo active aromatic sulfonamide compound (A), or at least 51 wt% of the halo active aromatic sulfonamide compound (A), or at least 75 wt% of the halo active aromatic sulfonamide compound (A), or at least 80 wt% of the halo active aromatic sulfonamide compound (A), or at least 90 wt% of the halo active aromatic sulfonamide compound (A), or at least 95 wt% of the halo active aromatic sulfonamide compound (A), or at least 99 wt%
  • the disinfecting composition used to form the residual dry-coat may comprise about 1 wt% of the halo active aromatic sulfonamide compound (A) and at least 1 wt% of the buffering agent (C), including about 1 wt% of the halo active aromatic sulfonamide compound (A) and from about 1 wt% to about 5 wt% of the buffering agent (C).
  • the halo active sulfonamide compound (A) may be, for example, a N-chloro-4-carboxybenzenesulfonamide compound of Formula (II):
  • R3 is COOR’;
  • R’ is hydrogen, an alkali metal, an alkaline earth metal, substituted C1-C12 alkyl, unsubstituted C1-C12 alkyl, substituted aromatic, or unsubstituted aromatic;
  • X is halogen;
  • M is an alkali or alkaline earth metal;
  • n is the number of water molecules per molecule of the sulfonamide compound.
  • a surfactant (D), or wetting agent can also be added to the disinfecting composition.
  • the surfactant decreases surface tension, allowing the sulfonamide compound to be spread more widely upon the surface to which it is applied. Both non- ionic and anionic surfactants can be used. However, in some specific embodiments, a surfactant is not used.
  • the surfactant (D) can be present in the disinfecting composition in the amount of about 0.0001 wt% to about 5 wt%.
  • a tracer fragrance (E) can also be included in the disinfecting composition if desired.
  • the tracer fragrance helps the user know where s/he has applied the disinfecting composition. Such tracer fragrances typically evaporate rapidly upon application, generally in under a minute.
  • the tracer fragrance can be present in the disinfecting composition in the amount of about 0.0001 wt% to about 5 wt%.
  • an alcohol (F) component can be included in the disinfecting compositions if desired.
  • the alcohol may be useful for changing surface tension, to solubilize fragrances, obtain a favorable odor profile, and obtain a quicker drying time.
  • the disinfecting composition may be an evaporative disinfecting composition. That is, the disinfecting composition may evaporate / dry over a short period of time to form a residual disinfectant coating (e.g. on a surface).
  • a residual disinfectant coating may be formed from a disinfecting composition as described herein and maintains antimicrobial properties for an extended period of time after application of the disinfecting composition and drying of the disinfecting composition.
  • the residual dry coating / layer contains the halo active aromatic sulfonamide organic compound.
  • the residual layer has a thickness that may vary as desired by the user.
  • the methods comprise applying an antimicrobial composition to a surface, wherein the antimicrobial composition comprises a halo active aromatic sulfonamide compound.
  • the disinfecting compositions can protect a variety of hard or soft surfaces, including but not limited to: metals, stainless steel, leather, gypsum board and drywall, painted surfaces, toilets, sinks, faucets, countertops, bedrails, beds, linens, light switches, hospital and other touchpoint surfaces, remotes, keyboard, cellphone, phones, communication devices, walls, toys, cushions, electronic buttons such as in elevators, money and currency, exercise equipment, rehabilitation equipment, paper, upholstery, and food preparation materials and equipment.
  • Hard surfaces can include those on desks, tables, chairs, beds, walls, windows, handles, floors, ceilings, toilets, sinks, electronic devices, handrails, etc.
  • Soft surfaces can include those on plastics (i.e.
  • the disinfecting compositions and residual dry coatings formed from the disinfecting compositions may be used on skin (e.g. human and/or animal skin).
  • the disinfecting compositions are contemplated to be especially useful in settings where large numbers of people may pass through.
  • Such settings can include, for example, a hospital, nursing home or long term care facility, school, jail or prison, a vehicle (e.g. automobile, train, airplane, bus, livery vehicle, etc.), a house, a public facility (airport, hotel, restaurant, restroom, etc.), a gym or workout facility, or a supermarket, or similar settings, just as a limited number of examples.
  • the disinfecting compositions can be applied to surfaces by spraying, electrostatic application, fogging, wipes, misting, or immersion, amongst other applications.
  • the disinfecting compositions can be combined (e.g. mixed) with a secondary material and then applied to a surface along with the secondary material.
  • the method may comprise forming a residual dry- coating on the intended surface.
  • the disinfecting compositions may be applied to the surface(s) in a wet form and allowed to evaporate over a period of time, thereby forming a residual dry-coat on the surface(s).
  • the intended surface may be skin, such as the skin of a human and/or animal.
  • the disinfecting compositions may also be applied to a surface or surfaces of an article during the manufacturing of the article.
  • the disinfecting composition may be impregnated into or otherwise applied to a surface of an article during the manufacturing process.
  • the halo active aromatic sulfonamide can be impregnated into articles including but not limited to: gypsum board and drywall, personal items such as toothpaste or mouthwash, building materials for commercial, industrial, and residential industry, toys, money and currency, paper, ink, sports equipment (not clothing), packaging materials, food preparation materials and equipment, and hard and soft surfaces.
  • the article is a bag, particularly a polymeric trash bag.
  • FIG. 6A is a perspective view of a multi-layer trash bag.
  • the trash bag 600 includes a first sidewall 602 and a second sidewall 604.
  • the two sidewalls 602, 604 are joined together along a first side edge 606, a second side edge 608 opposite the first side edge, and a bottom edge 610 extending between the first and second side edges 606, 608.
  • the bag has a top edge 611 opposite the bottom edge which is not sealed, and when the bag is expanded, an opening 612 is formed through which items are thrown into the internal volume of the trash bag.
  • the sealed edges 606, 608, 610 can be made by, for example, heat sealing two separate multi-layer films together along all three edges 606, 608, 610.
  • a single large multi-layer film could be folded in half (the fold line corresponding to bottom edge 610) and the two side edges could be sealed together.
  • a draw tape 614 that acts as a closure mechanism for the trash bag, and which is visible through apertures along the top edge.
  • FIG. 6B is a cross-sectional view of one of the sidewalls of the trash bag of FIG. 6A.
  • the sidewall 620 is formed from a multi-layer film.
  • the sidewall 620 is illustrated as having a first film layer 630 and a second film layer 640 (of course, the multi-layer film can contain additional layers).
  • the first film layer 630 has an interior surface 632 and an exterior surface 634.
  • the second film layer 640 also has an interior surface 642 and an exterior surface 644.
  • the interior surfaces 632, 642 of the two film layers face each other, and are laminated together.
  • the exterior surface 634 of the first film layer faces the internal volume of the trash bag, while the exterior surface 644 of the second film layer also forms the outer surface of the trash bag itself.
  • the two film layers may have thicknesses as desired.
  • the first film layer 630 may be relatively permeable to gases and liquids. It is contemplated that the dry disinfectant coating / layer could be located in multiple locations. First, the dry disinfectant coating could be located on the exterior surface 634 of the first film layer, or in other words on the inner surface of the trash bag (indicated with reference numeral 650). Second, the dry disinfectant coating could be located on one of the interior surfaces 632, 642 of the film layers, or in other words between the two film layers 630, 640 of the trash bag (indicated with reference numeral 652).
  • the dry disinfectant coating could be located on the exterior surface 644 of the second film layer, or in other words on the outer surface of the trash bag (indicated with reference numeral 654).
  • the dry disinfectant coating / layer may be uniformly formed across the entire film layer, or preferentially formed in desired locations such as along the top edge / opening of the trash bag.
  • the dry disinfectant coating may be formed at any one or combination of these locations.
  • the dry disinfectant coating / layer containing the halo active aromatic sulfonamide compound can be exposed to water (e.g. permeating through the film layer) that hydrates the sulfonamide compound and permits its active antimicrobial ability.
  • the treated surface may maintain antimicrobial effect for over 24 hours, or over 48 hours, or over 72 hours, or over 168 hours, or over 336 hours, or longer.
  • the disinfecting compositions of the present disclosure may achieve high microbial killing performance over extended periods of time.
  • the disinfecting composition can maintain a killing performance after drying (i.e. in residual dry-coat form) of at least 85% after 24 hours, or at least 90% after 24 hours, or at least 95% after 24 hours, or at least 98% after 24 hours, or at least 85% after 48 hours, or at least 90% after 48 hours, or at least 95% after 48 hours, or at least 98% after 48 hours, or at least 85% after 72 hours, or at least 90% after 72 hours, or at least 95% after 72 hours, or at least 98% after 72 hours, or at least 85% after 168 hours, or at least 90% after 168 hours, or at least 95% after 168 hours, or at least 98% after 168 hours, or at least 85% after 336 hours, or at least 90% after 336 hours, or at least 95% after 336 hours, or at least 98% after 336 hours.
  • Disinfecting compositions containing 1 wt%, 0.5 wt%, 0.25 wt%, 0.1 wt%, 0.05 wt%, and 0.025 wt% of N-chloro-4-carboxybenzenesulfonamide (BENZ), and a vehicle control solution were prepared. Approximately 5 mL of each solution was added to a sterile polystyrene petri dish, completely covering the surface, and allowed to evaporate and dry coat the plate surface overnight. After drying, the coated plates were stored at room temperature.
  • bacterial solutions were added as 25 pi drops at several locations on each plate.
  • Bacterial solutions of S. aureus and P. aeruginosa (laboratory stocks purchased from ATCC) were prepared from 24-48 hour freshly grown bacterial monolayers on Tryptic Soy Agar (TSA) plates. The bacterial monolayer was removed from the plate surface with a sterile loop and transferred to 10 ml sterile saline. The resulting solutions were visibly turbid and by comparison to McFarlan standards estimated to contain between 1x10 8 to 1x10 9 bacteria per ml. Thus, 25mI drops corresponding to about 5x10 6 total bacteria were added at several replicate locations on each plate.
  • the bacterial spots were swabbed off of the plate surface with a sterile moistened cotton swab and diluted in 2 ml sterile saline.
  • a 96-well dilution plate was used to prepare an end-point dilution series to determine the number of recoverable bacteria.
  • Each dilution well was filled with 720pl_ of tryptic soy broth (TSB).
  • TBS tryptic soy broth
  • An 80mI_ sample was taken from each swab sample tube and placed in the top dilution well.
  • a 1 : 10 (80mI_: 800mI_) dilution series was performed down the plate with 80mI_ samples being transferred down the plate.
  • FIG. 2 and FIG. 3 the test results with respect to S. aureus are shown after 24 hours and 14 days of exposure to the dry-coat disinfecting compositions.
  • the average amount of live bacteria from two technical replicate titrations of 2-3 biological/experimental replicates are illustrated.
  • At all tested concentrations of the disinfecting composition there was a 5 logio or greater reduction in viability of S. aureus added to the surface 1 day after the addition of the disinfecting composition, which corresponds to a 99.99% to 99.999% reduction in bacterial load.
  • a similar bactericidal effect was seen when adding S. aureus 7 days after dry-coating the surface with the disinfecting composition.
  • At 14 days after dry-coating there was a 4-6 logio reduction in viability of S. aureus.
  • Concentrations of the disinfecting composition of 0.05 wt% or higher reduced the amount of S. aureus to levels below the limits of detection.
  • Disinfecting compositions containing 4 wt% of N-chloro-4- carboxybenzenesulfonamide (BENZ), and a vehicle control solution were prepared. Approximately 5 mL of each solution was added to sterile non-hydrophobic tissue culture dishes, completely covering the surface, and allowed to evaporate and dry coat the plate surface overnight. After drying, the coated plates were stored at room temperature.
  • Cd1 is Isolate 201 10870, PCR ribotype 027, containing the tcdA, B, and C genes of the PaLoc operon and the C. difficile binary toxin (CDT).
  • Cd2 is Isolate 20120166, PCR ribotype 002, containing the tcdA, B, and C genes of the PaLoc operon and is negative for the C.
  • Cd3 is Isolate 201 10963, PCR ribotype 017, containing the tcdA, B, and C genes of the PaLoc operon and is negative for the C. difficile binary toxin (CDT).
  • Bacterial endospore solutions were added as 25 pi drops at several locations on each dish and allowed to dry. Swab samples of the plate areas containing dried spores were taken at 24 hours, 2 days, and 7 days after spore addition to the dry-coated plates. Spore solutions were counted microscopically and final concentrations ranged between 1x10 9 to 1x10 10 spores per ml.

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Abstract

L'invention concerne des compositions antimicrobiennes utilisées pour former un revêtement sec résiduel comprenant un composé de sulfonamide aromatique halo-actif de formule (I) : les variables R1, R2, R3, R4, R5, X, M et n étant décrites dans le présent document. Les compositions et les procédés les utilisant peuvent être utilisés en tant que revêtement sec ou couche sèche pour maintenir des surfaces désinfectées avec un comptage microbien réduit pendant des périodes de temps prolongées allant de plusieurs jours jusqu'à plusieurs semaines.
PCT/US2019/043256 2018-07-26 2019-07-24 Compositions antimicrobiennes de sulfonamide aromatique halo-actif WO2020023645A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022035421A1 (fr) * 2020-08-11 2022-02-17 Rem Brands, Inc. Revêtements désodorisants et antimicrobiens à base de sulfonamide aromatique halo actif

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2071625A (en) * 1931-06-03 1937-02-23 W E Long Co Preservation of packaged food products
FR2744919A1 (fr) * 1996-02-21 1997-08-22 Stoa Sa Nouvelles compositions pour le traitement et la protection des mamelles des animaux de traite
RO114628B1 (ro) * 1992-07-22 1999-06-30 S.C. Sintofarm S.A. Detergent lichid, concentrat, cu efect dezinfectant
WO1999065305A1 (fr) * 1998-06-15 1999-12-23 Eurospital S.P.A. Preparation desinfectante contenant du chlore dans l'alcool
WO2002010328A1 (fr) * 2000-07-14 2002-02-07 Lee Chang Sub Composition detergente a effet germicide pour articles de table
DE10236096A1 (de) * 2002-08-01 2004-02-12 Rmp Chemisch-Technische Spezialprodukte Gmbh & Co Kg Mittel enthaltend Chloramin T und/oder B
US20040225017A1 (en) * 2003-05-06 2004-11-11 Schneider Charles A. Chloramine T based teat cleaner and related process
KR100632926B1 (ko) * 2005-06-17 2006-10-11 해동화학(주) 살균 조성물
US20060280766A1 (en) * 2002-02-19 2006-12-14 Sat, Inc. Active aromatic sulfonamide organic compounds and biocidal uses thereof
WO2007022453A2 (fr) * 2005-08-19 2007-02-22 Sat, Inc. Composes organiques actifs de sulfamide aromatique et utilisation de ces derniers en tant que biocides
EP1932425A2 (fr) * 2006-12-14 2008-06-18 I.C.F. S.r.l. Désinfectant en poudre pour les tétines d'animaux laitiers
US20110251284A1 (en) * 2002-02-19 2011-10-13 Charles A. Schneider and David J. Schneider Halo active aromatic sulfonamide organic compounds and uses therefor
WO2011143376A1 (fr) * 2010-05-14 2011-11-17 Schneider David J Compositions pour l'élimination des odeurs, à faible teneur en chlore
US20110301241A1 (en) * 2002-02-19 2011-12-08 Schneider David J New halo active aromatic sulfonamide organic compounds and uses therefor
RU2489530C1 (ru) * 2012-04-26 2013-08-10 федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Южно-Российский государственный технический университет (Новочеркасский политехнический институт)" Электролит для осаждения композиционного покрытия никель-кобальт-оксид кремния-фторопласт
US20160158404A1 (en) * 2010-05-14 2016-06-09 Rem Brands, Inc. Articles with odor-controlling composition
WO2016108041A1 (fr) * 2014-12-30 2016-07-07 Trio Healthcare Limited Compositions anti-biofilm
WO2016130588A1 (fr) * 2015-02-09 2016-08-18 Rem Brands, Inc. Articles comprenant une composition anti-odeurs

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2071625A (en) * 1931-06-03 1937-02-23 W E Long Co Preservation of packaged food products
RO114628B1 (ro) * 1992-07-22 1999-06-30 S.C. Sintofarm S.A. Detergent lichid, concentrat, cu efect dezinfectant
FR2744919A1 (fr) * 1996-02-21 1997-08-22 Stoa Sa Nouvelles compositions pour le traitement et la protection des mamelles des animaux de traite
WO1999065305A1 (fr) * 1998-06-15 1999-12-23 Eurospital S.P.A. Preparation desinfectante contenant du chlore dans l'alcool
WO2002010328A1 (fr) * 2000-07-14 2002-02-07 Lee Chang Sub Composition detergente a effet germicide pour articles de table
US20060280766A1 (en) * 2002-02-19 2006-12-14 Sat, Inc. Active aromatic sulfonamide organic compounds and biocidal uses thereof
US20110251284A1 (en) * 2002-02-19 2011-10-13 Charles A. Schneider and David J. Schneider Halo active aromatic sulfonamide organic compounds and uses therefor
US20110301241A1 (en) * 2002-02-19 2011-12-08 Schneider David J New halo active aromatic sulfonamide organic compounds and uses therefor
DE10236096A1 (de) * 2002-08-01 2004-02-12 Rmp Chemisch-Technische Spezialprodukte Gmbh & Co Kg Mittel enthaltend Chloramin T und/oder B
US20040225017A1 (en) * 2003-05-06 2004-11-11 Schneider Charles A. Chloramine T based teat cleaner and related process
KR100632926B1 (ko) * 2005-06-17 2006-10-11 해동화학(주) 살균 조성물
WO2007022453A2 (fr) * 2005-08-19 2007-02-22 Sat, Inc. Composes organiques actifs de sulfamide aromatique et utilisation de ces derniers en tant que biocides
EP1932425A2 (fr) * 2006-12-14 2008-06-18 I.C.F. S.r.l. Désinfectant en poudre pour les tétines d'animaux laitiers
WO2011143376A1 (fr) * 2010-05-14 2011-11-17 Schneider David J Compositions pour l'élimination des odeurs, à faible teneur en chlore
US20160158404A1 (en) * 2010-05-14 2016-06-09 Rem Brands, Inc. Articles with odor-controlling composition
RU2489530C1 (ru) * 2012-04-26 2013-08-10 федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Южно-Российский государственный технический университет (Новочеркасский политехнический институт)" Электролит для осаждения композиционного покрытия никель-кобальт-оксид кремния-фторопласт
WO2016108041A1 (fr) * 2014-12-30 2016-07-07 Trio Healthcare Limited Compositions anti-biofilm
WO2016130588A1 (fr) * 2015-02-09 2016-08-18 Rem Brands, Inc. Articles comprenant une composition anti-odeurs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 199937, Derwent World Patents Index; AN 1999-442556, XP002794651 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022035421A1 (fr) * 2020-08-11 2022-02-17 Rem Brands, Inc. Revêtements désodorisants et antimicrobiens à base de sulfonamide aromatique halo actif

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