EP4165152A1 - Textilbehandlungsmittel - Google Patents

Textilbehandlungsmittel

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Publication number
EP4165152A1
EP4165152A1 EP21822880.7A EP21822880A EP4165152A1 EP 4165152 A1 EP4165152 A1 EP 4165152A1 EP 21822880 A EP21822880 A EP 21822880A EP 4165152 A1 EP4165152 A1 EP 4165152A1
Authority
EP
European Patent Office
Prior art keywords
chloride
composition
imidazolinium
liquid composition
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21822880.7A
Other languages
English (en)
French (fr)
Inventor
Bruce Smyth
Michael BRALKOWSKI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Enviro Specialty Chemicals Inc
Original Assignee
Enviro Specialty Chemicals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Enviro Specialty Chemicals Inc filed Critical Enviro Specialty Chemicals Inc
Priority claimed from PCT/US2021/037298 external-priority patent/WO2021253015A1/en
Publication of EP4165152A1 publication Critical patent/EP4165152A1/de
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/645Mixtures of compounds all of which are cationic
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, 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
    • A01N25/08Biocides, 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 containing solids as carriers or diluents
    • A01N25/10Macromolecular compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N55/00Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62BDEVICES, APPARATUS OR METHODS FOR LIFE-SAVING
    • A62B23/00Filters for breathing-protection purposes
    • A62B23/02Filters for breathing-protection purposes for respirators
    • A62B23/025Filters for breathing-protection purposes for respirators the filter having substantially the shape of a mask
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds

Definitions

  • the present invention relates to a chemical treatment that may be applied to a protective article.
  • the invention relates to material compositions for controlling the spread of pathogens and infection diseases.
  • the present invention relates to antimicrobial and antiviral compositions, a method of manufacturing or treating a textile material, such as woven and non-woven textiles, yarn and/or fiber, with antimicrobial and antiviral compounds in such a manner to chemically bind or attach said compounds to the textile material, and to the treated textile material which performs as a disinfectant or sterilizer on its own.
  • the treated textile material exhibits wash-durability and non- leaching properties, and can be provided with multifunctional enhancements, such as hydrophobic properties on the surface.
  • the present invention is also directed to a textile material to which one or more antimicrobial or antiviral agents are adhered.
  • the agent(s) is/are adhered to the textile material in such a manner that they are not released from the textile even if the textile is wetted or washed, so that the textile is reusable. Washability and/or usability of the textile are improved where one or more agents are adhered to the textile.
  • the textile material can be used, e.g., in a reusable textile product.
  • the invention further relates to a method of finishing a textile material by applying and binding antimicrobial and/or antiviral agents to the textile material so that the agents are essentially irreversibly adhered to the finished textile material.
  • Sanitizer Disinfectant Sterilizer es nts s Textile materials like woven and non-woven fabrics, yarns and/or fibers are used for a variety of purposes and in a variety of environments. As such, there is a realistic danger of microbiological contamination on the textile surfaces. These substrates are used to filter air or water, but work only by blocking, and do not eliminate the contamination. In recent times, studies have shown that textiles carry nosocomial infections from patient to patient in hospitals. Soldiers often wear clothes for extended periods of time, without washing, which often results in fungal and bacterial infection to the wearer. Danger of staining of apparel due to ketchup, honey, sputum, blood, human excreta and moisture are also problems faced by users in various circumstances.
  • the mattresses and pillows are also likely to become infected due to the fact that these are not washed. They, in turn, can transmit infection to the patient.
  • Sheets, pillow covers, gowns, and curtains are subjected to contamination from open wounds and other medical conditions, such as coughing, wheezing, etc.
  • Patients' gowns are contaminated by sweat and/or human excretion such as urine, stool and vomit. This leads to the growth of microorganisms like bacteria, viruses and fungi.
  • Healthcare workers are very often subjected to the contamination either from soiled textiles used by patients or due to excretions of the body. Medical personnel are major causes of transmitting bacterial infection from one patient to another. Current medical textiles offer no barrier protection.
  • Industrial, medical and home fabric softener of interest are liquid compounds that alters the textile product’s fibers by coating the fibers and making the textile product feel better to the touch (known as hand).
  • the softening agents applied are hygroscopic or lubricating agents, which allow for the fibers to slide within the fabric structure, assisting with easier deformation and creasing of the fabric. The duration of the effect is temporary since the softeners applied during the treatment are eliminated by future machine washings.
  • a number of textile softener chemistries exists such as anionic and cationic surfactants, siloxane polymeric- based softeners and non-ionic surfactant softeners.
  • Fabric softeners work by depositing lubricating oil type chemicals on the fabric that make it feel softer, reduce static cling, and remove odors or impart a fresh fragrance.
  • the textile garment and hosiery industries have treated textile fabrics in the mills with antimicrobial agents to reduce the attraction and population growth of bacteria. The result is a reduction in odors generated by the bacteria on the garments and hosiery.
  • Application of the antimicrobial agent is done by padding, spraying or foaming an ingredient or ingredients onto fabric and fusing the chemistry into the fabric (heat setting) in a heating tunnel for a more permanent treated garment.
  • Grey US 4,166,794 teaches a combination product of a liquid, bleach softener composition for use in one or more of the wash, rinse and tumble dry cycles of a laundering process comprising a water soluble peroxy bleaching agent and a water soluble cationic nitrogen softener compound, at least 50% thereof being an aliphatic, quaternary ammonium compound and/or a cationic heterocyclic imide such as an imidazolinium or pyridinium compound. Grey does not mention the incorporation of antimicrobial agents to reduce micro-organism populations.
  • the peroxy bleaching agent was for the removal of food or beverage stains.
  • US 4,184,004 to Pines et al discloses fabrics namely cellulose and blends of cellulose and polyester that can be treated with the trimethoxysilyl functional groups of a terpolymer chemistry using the siloxane and an epoxy polyoxyalkylene. The results produced a soft hydrophilic fabric.
  • US patent 4,425,372 to Baldwin reveals industrial chemical biocidal methodologies to make antimicrobial, non-leachable fabrics using Dimethyloctadecyl 3-trimethoxysilyl propyl chloride as the bactericidal and bacteriostatic chemistry.
  • Concentrations ranging from 0.2 to 1.1 wt% are used as coatings and approved by EPA and FDA for medical devices such as drapes and pre-op fabrics.
  • Baldwin states a 95% efficacy against bacteria in one hour but did not disclose the species.
  • Baldwin did not consider the evolution of bacteria within hospital settings due to horizontal gene transfer of Staphylococcus aureus to become resistant to antibiotics (methicillin) and making the MRSA more difficult to kill with the one biocide namely the dimethyloctadecyl 3-trimethoxysilyl propyl chloride.
  • Baldwin does not disclose the addition of a textile softener and the combined synergies.
  • US Patent 4,721,511 to Kupits describes a leach resistant antimicrobial fabric namely a non woven cellulose, polyethylene, or polypropylene treated with (3-trimethoxysilyl) propyl octadecyl dimethyl ammonium chloride and an organic titanate.
  • Humans are exposed to bacteria in much of their environment on a 24-hour daily basis. There are beneficial species of bacteria however humans who are immune compromised can be more susceptible to infections.
  • Clostridium difficile spores float in the air until nine spores combine to form a terminal loading which then allows the grouping to fall due to gravity. The result if contacted and ingested results in illness.
  • the anti-microbial, anti-viral, fabric softener compounds also imparts antimicrobial efficacy to the wash water during the rinse cycle and will impart a bacteriostatic environment on the washing machine interior walls.
  • the invention provides a liquid antimicrobial and antiviral fabric treating composition comprising:
  • Ri is an C 1-30 alkyl group, preferably C 8-30 alkyl group
  • R 2 and R 3 , R 4 and R 5 each independently are an C 1-30 alkyl group or hydrogen
  • X is a counter ion, such as CT, Br ' , I' or
  • a purpose of this invention is to expand upon the fabric softeners benefits by the addition of incorporating antimicrobial properties to the fabric during the same wash machine rinse cycle treatment. The results would reduce or kill bacteria on the fabric fibers, and reduce odors, while making the garments soft and more appealing to the touch.
  • Antimicrobial treated fabric would affect population growth of micro-organisms on the fabric and the spreading of micro-organisms from one contact point to another contact point.
  • the continued evolution of micro-organisms species to generate resistant strains due to horizontal gene or RNA transfer poses a more aggressive response to antimicrobial discipline in community environmental settings such as adult care facilities as well as health care environments.
  • the chemistry of a trimethoxy silane quat to impinge onto the fibers as an antimicrobial mesoporous self-assembling silane polymeric allows for a persistence efficacy of antimicrobial properties.
  • the chemistry is heat set onto the fibers during the drying of fabrics.
  • the compounds also treat the water and washing machine interior to include sealing gaskets preventing mold and odors.
  • the compositions of the present invention include a combination of substances, which have microbicidal synergistic effects. The synergistic effect reduces the need to use large quantities of biocides. Kupits does not state of killing MRSA nor does he state of additional fabric softener adds.
  • the imidazolinium compounds used in the present invention are Imidazolium compounds, 4,5-dihydro-1-methyl-2-nortallow alkyl-1-(2- tallow amidoethyl), Me sulfates. Tallow fatty acid or palm oil stearin are included in this dimethyl sulfate quat. Also included are the triethanolamine fatty acid esters in the present invention, commercial mixtures of fatty acids or fatty acid methyl esters, such as those having from 10 to 20 carbon atoms may be used as the dimethyl sulfate quat known as ester quats.
  • a primary object of the present invention is to provide a liquid fabric conditioning composition wherein treatment of the textile fabric can attain a superior soft hand feel by treating in the wash machine rinse cycle.
  • a further object of the invention is to provide a liquid laundry additive which is a sanitizing laundry antimicrobial capable of reducing bacteria > 99.9% (a 3-log 10 reduction) both on the fabric and in the laundry water. Thereby the fabric-softener composition is capable of simultaneously and effectively mitigate bacteria and softening fabrics treatment therewith.
  • a still further object of the invention is to provide a liquid laundry additive composition which provides a residual self-sanitizing activity over a time period from 1 hour to 60 days. Once the fabric is treated in the rinse cycle and dried in an automatic machine washing and drying operation, the fabric will provide a reduction of greater than 99.9% in some bacteria and virus over the control count for both the fabric and laundry water within the contact time claimed.
  • the invention includes a process of conditioning fabrics by simultaneous sanitizing and softening thereof comprising contacting said fabrics in one or more of the wash, rinse and tumble drying cycles of a laundering process with an effective sanitizing and softening amount of the composition above described.
  • antimicrobial refers to the capability of an article to destroy (kill) , inhibit the growth or reproduction of, immobilize and/or remove microorganisms, for example bacteria, fungi, yeasts and algae.
  • antiviral refers to the capability of an article to destroy (kill) , inhibit the growth or reproduction of, immobilize and/or remove viruses .
  • the compositions of the present invention provide anti-microbial and antiviral protection to fabrics. The also provide anti-viral protection against corona-viruses and more in particular Covid 19 also known as SARS-2.
  • compositions of the present invention are stable aqueous compositions which contain as the active fabric softening components cationic fabric softeners or mixtures thereof which is preferably a water-dispersible quaternary ammonium compound salt or a water dispersible alkyl imidazolinium compound salt or a water dispersible alkyl imidazolinium compound salt as hereinafter described in more detail, and or other ingredients such as fatty alcohols, nonionic ethoxylated or propoxylated alcohols also as hereinafter described.
  • cationic fabric softeners or mixtures thereof which is preferably a water-dispersible quaternary ammonium compound salt or a water dispersible alkyl imidazolinium compound salt or a water dispersible alkyl imidazolinium compound salt as hereinafter described in more detail, and or other ingredients such as fatty alcohols, nonionic ethoxylated or propoxylated alcohols also as hereinafter described.
  • the aqueous compositions of this invention contain as the first active fabric softening component at least one cationic fabric softener in an amount generally ranging from about 74 to 86% by weight, preferably from about 75 to 85% by weight of the total active fabric softening components (cationic fabric softener plus other ingredients), or on the basis of the total aqueous composition, the amount will be: for a concentrated formulation, from about 8 to 15% by weight, preferably from about 10 to 13%, by weight and for a ready-to-use formulation from about 2.2 to 7%, preferably from about 2.3 to 6.6%, by weight. It is understood, of course, that a ready-to-use product is one for which the consumer is instructed to use the product at full strength (i.e.
  • a concentrated formula is one for which the consumer is instructed to dilute the product (e.g. from about 1 to 4X) to make up the required dosage, e.g. 1/4 to 1/2 cup per load of wash. Accordingly, it is clear that for the preferred concentrated formula, the consumer will have at least the perceived notion of greater economy and flexibility in use.
  • Softening agents are used to render fabrics or textile soft, and the terms "softening” and “softener” refer to the handle, hand, touch, or feel; this is the tactile impression given by fabrics or textiles to the hand or body and is of aesthetic and commercial importance.
  • the cationic fabric softeners used in the present invention can be any of the commercially available and known cationic fabric softeners and preferably are of the water-dispersible quaternary ammonium compound salt or alkyl imidazolinium compound salt type including at least one, and preferably two hydrophobic groups containing at least 12 and preferably at least 14 carbon atoms.
  • a first preferred class of the cationic fabric softener active ingredient are the imidazolinium compounds of the formula I: whe rein R 4 is hydrogen or lower alkyl of 1 to 4 and preferably 1 to 3 and especially preferably 1 or 2 carbon atoms, R 5 is an alkyl containing from 9 to 25 carbon atoms, preferably linear higher alkyl of from about 13 to 23 and especially preferably 13 to 19 carbon atoms, R 6 is an alkyl containing from 8 to 25 carbons and preferably a substantially linear higher alkyl group of about 13 to 23, and preferably 13 to 19 carbon atoms; R 7 is hydrogen or an alkyl containing from 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms, and X is as defined above.
  • alkyl imidazolinium compounds of formula I include: methyl-1-tallow amido-ethyl-2-tallow imidazolinium methyl sulfate, methyl-1-oleyl amido-ethyl -2-oleyl imidazolinium methyl sulfate, 1-methyl-1-(palmitoylamido)-ethyl-2-octadecyl-4,5-dihydroimidazolinium chloride, 2-hepadecyl-1-methyl-1-(2-stearylamido)-ethyl-imidazolinium chloride, 2-lauryl-1-hydroxyethyl-1-oleyl-imidazolinium chloride, 2-tallow-1-(2-stearoyloxyethyl)-imidazoline chloride, 2-tallow-1-(2-stearoyloxyethyl)-imidazoline sulfate, 2-tallow-1-(2-stearoyloxyethyl)-imidazoline
  • R represents a hydrocarbyl group of from about 12 to 24 and preferably about 14 to 22 carbon atoms
  • Ri represents lower alkyl of 1 to 4, preferably 1 to 3, carbon atoms, or a hydrocarbyl group of from 12 to 24, preferably 14 to 22, carbon atoms
  • R 2 and R 3 represent lower alkyl of 1 to 4, preferably 1 to 3, carbon atoms
  • X represents an anion capable of imparting water solubility or dispersibility, such as halide, e.g. chloride, bromide and iodide; sulfate, methosulfate, nitrite, nitrate, phosphate, and carboxylate, e.g.
  • the hydrocarbyl groups are preferably alkyl but may be alkenyl, aryl, or aralkyl and may include various substituents or interrupting groups such as halo, amide, hydroxyl, and carboxyl substituents or interrupting functional groups and ethoxy or polyethoxy interrupting groups.
  • substituents or interrupting groups such as halo, amide, hydroxyl, and carboxyl substituents or interrupting functional groups and ethoxy or polyethoxy interrupting groups.
  • one or more of the lower alkyl groups may also be substituted, for example, by an hydroxy group.
  • Typical cationic fabric softener compounds of formula IP include the following: distearyl dimethyl ammonium chloride, ditallow dimethyl ammonium chloride, dihexadecyl dimethyl ammonium chloride, distearyl dimethyl ammonium bromide, di (hydrogenated tallow) dimethyl ammonium bromide, distearyl di(isopropyl)ammonium chloride, distearyl dimethyl ammonium methosulfate and dilauryldimethylammonium chloride.
  • a highly preferred class of the cationic fabric softeners of formula PI are the water- insoluble compounds wherein the groups R and R 1 are C 14 to C 18 , R 2 is methyl or ethyl and R 3 is methyl, ethyl, isopropyl, n-propyl, hydroxyethyl or hydroxypropyl.
  • the water dispersible cationic fabric softeners which can be used in the compositions of the present invention are not limited to those described above and any of the other known useful water dispersible cationic fabric softeners can be used. Furthermore, mixtures of the above mentioned cationic fabric softeners can also be used.
  • the anti-microbial and antiviral component of the formulation is a suitable organosilicon quaternary ammonium salt compound represented by Formula F wherein R 1 is an C 1-30 alkyl group, preferably C 8-30 alkyl group, R 2 and R 3 , R 4 and R 5 each independently are an C 1-30 alkyl group or hydrogen, and X is a counter ion, such as Cl-, Br-, I- or CH3COO-
  • a preferred organosilicon quaternary ammonium salt has the structural formula
  • organosilicon quaternary ammonium salt compounds for use according to the invention are 3-(triethoxysilyl)-propyl-dimethyloctadecyl ammonium chloride, 3-(tri-methoxysilyl) propyl-methyl-dioctyl ammonium chloride, 3-(trimethoxysilyl) propyl- dimethyl-decyl ammonium chloride, 3-(trimethoxysilyl)-propyl-methyldidecyl ammonium chloride, 3- (trimethoxysilyl) propyldimethyldodecyl ammonium chloride, 3-(tri-methoxysilyl)- propyl-methyldidodecyl ammonium chloride, 3-(trimethoxysilyl) propyl-dimethyltetradecyl ammonium chloride, 3-(trimethoxysilyl)-propyl-methyldihexadecyl ammonium chloride, 3-
  • the concentration of the organosilicon quaternary is in the range of 1-5% by weight and more preferably in the range of 1-2.5% by weight.
  • Aqueous or alcoholic solutions of the compositions of the invention can be used to treat textiles, minerals, glass and many other substrates, to render the surfaces of the substrates resistant to the growth of microorganisms or viruses.
  • the textile fabrics treated with the compositions of the invention have free hydroxy groups on their surfaces.
  • the composition is not readily washed off or leached from the treated substrate surface by water. It is believed that this phenomenon results from the formation of covalent bonds between the silyl moiety of the silicon qauternary and the free hydroxy groups on the surface of the substrate, whereby the composition is chemically bonded to the substrate's surface.
  • any substrate having free hydroxy groups on its surface can be usefully treated with the composition of the invention.
  • the substrates having free hydroxy groups on their surfaces which can be suitably bonded to the organosilicon quaternary ammonium compounds, are natural and man-made fiber fabrics, such as cotton, wool, linen, felt, acrylic, polyester, cellulose acetate, rayon, nylon and vinyl, and metals such as aluminum, stainless steel and galvanized metal, as well as wood, rubber, paper, glass and ceramic.
  • this antimicrobial silicon containing quaternary ammonium agent imparts a durable, wash resistant, broad spectrum biostatic surface antimicrobial and antiviral finish to a substrate.
  • the organosilicon quaternary ammonium compound is leach resistant, nonmigrating and is not consumed by microorganisms. It is effective against gram positive and gram negative bacteria, viruses, fungi algae, yeasts, mold, rot and mildew.
  • the silicone quaternary ammonium salt provides durable, bacteriostatic, virucidal, fungistatic and algistatic surfaces. It can be applied to organic or inorganic surfaces as a dilute aqueous or solvent solution of 0.1-1.5 percent by weight of active ingredient. After the alkoxysilane is applied to a surface, it is chemically bonded to the substrate by condensation of the silanol groups at the surface.
  • the pure compound is crystalline whereas methanol solutions of the compound are low viscosity, light to dark amber liquids, soluble in water, alcohols, ketones, esters, hydrocarbons and chlorinated hydrocarbons.
  • the compound has been used in applications such as, for example, socks, filtration media, bed sheets, blankets, bedspreads, carpet, draperies, fire hose fabric materials, humidifier belts, mattress pads, health care apparel, mattress ticking, underwear, nonwoven disposable diapers, nonwoven fabrics, outerwear fabrics, nylon hosiery, vinyl paper, wallpaper, polyurethane cushions, roofing materials, sand bags, tents, tarpaulins, sails, rope, blood pressure cuffs, athletic and casual shoes, shoe insoles, shower curtains, toilet tanks, toilet seat covers, throw rugs, towels, umbrellas, upholstery fiberfill, intimate apparel, wiping cloths and medical devices such as blood pressure cuffs.
  • compositions of the invention are prepared by dissolving the components in water.
  • the resulting aqueous solutions may also include nonionic surfactants, phenoxyethanol and fragrances.
  • the compositions may also contain one or more optional additives selected from the group consisting of perfumes, dyes, pigments, opacifiers, optical brighteners, anti-corrosion agents, and preservatives, the amount of each additive being up to 0.5% by weight, and
  • the starting textile material can be treated with one or more further antimicrobial agents, in particular at least one selected from the group consisting of benzalkonium chloride; benzethonium chloride; benzoxonium chloride; dequa- linium; vinylbenzyltrimethylammonium chloride; cetrimonium bromide, optionally in combination with reactive amino silicone having alkoxy groups like hydroxyl or methoxy or ethoxy groups; 2-phenylphenol, Acibenzolar, Paclobutrazol, Azoxystrobin, Epoxiconazole, Bina
  • the further antimicrobial agent is preferably used in an amount of 0.1 to 10% by weight, in particular in an amount of 0.1 to 5%, 0.1 to 3% or 0.1 to 1% by weight, based on the weight of the textile material.
  • Nonionic materials may also be incorporated in the compositions of the invention.
  • Typical non-ionics include alkylphenoxypolyethoxyethanols having alkyl groups of about seven to eighteen carbon atoms and 6 to 60 or more oxyethylene units, such as heptyl- phenoxypolyethoxyethanols, octylphenoxynonylphenoxyethanols, dodecylphenoxypolyethoxy- ethanols, and the like; and polyethoxyethanol derivatives of methylene-linked alkyl phenols.
  • the invention incorporates cationic compounds in solution to perform several functions.
  • EXAMPLE I In the first set of formulations, two distinct chemistries were combined namely a cationic softening agent, 4,5 Dihydro-1-methyl-2-nortallow alkyl-1-(2-tallow amidoethyl) imidazolinium compound methyl sulfates; and a cationic biocide namely, 1-Octadecanaminium-N,N-Dimethyl- N-[(3-trimethoxysilyl) propyl] chloride.
  • Imidazolinium DMS quaternaries are considered the best softeners on an activity basis providing exceptional softening properties in addition to providing superior static control.
  • Table 4.4 shows the efficacy for Pseudomonas aeruginosa was log 2.2.
  • Table 4.5 shows the efficacy for MRSA was log 6.1.
  • TABLE 3 FORMULATIONS FOR LAUNDRY COMPLETE CHEMICAL NAME TRIAL 6 TRIAL 7 TRIAL 8 TRIAL 9 TRIAL10 WT% WT% WT% WT% WT% 4,5 Dihydro-1-Methyl-2-Nortallow 12.5 12.5 12.5% 12.5 6.25
  • Table 4.1 Quantatative Method For Antimicrobial Efficacy By Absorbtion Method JIS L 1902:2008 For Staphyloccocus Aureus Attc 6538 For Laundry Complete Table 3 Formula Trial 8 HRS CONCENTRATION DIFFERENCE OF DIFFERENCE OF GROWTH GROWTH ANTIMICROBIAL OF INOCULUM EXTREMES EXTREMES VALUE OF F VALUE OF G ACTIVITY Table 4.2 Quantatative Method For Antimicrobial Efficacy By Ab
  • the compounds were mixed in 50o C Demineralized water with and without surfactants. Stable emulsions were made, and viscosities were suitable for the 7.5% by wt 4,5 dihydro-1-methyl-2-nortallow alkyl-1(2-tallow amidoethyl) imidazolium compounds methyl sulfates
  • MHV-S was grown in a mouse liver cell line, NCTC clone 1469. Isolated virus was incubated with a dilution of the Laundry Complete based on its use instructions, at room temperature for 15 minutes. The samples were then neutralized and passed over a dextran bead column to remove potential cytotoxic substances. Column eluates were used to inoculate NCTC clone 1469 cells in a 96 well plate. After 7 days the wells were examined for cytopathological effects (CPE) in the cells and scored accordingly. The protocol followed DIN EN-14476 European Standard for Quantitative Suspension Test of Chemical Disinfectants and Antiseptics for Virucidal Activity, Dec.2015.
  • CPE cytopathological effects
  • NCTC Clone 1469 (ATCC® CCL-9.lTM) was maintained in DMEM with 4500 g/1 glucose plus L-gln and 1.5g/l sodium bicarbonate, pH 7.3, supplemented with 10% Donor Horse Serum (Biotechne, Minneapolis, MN) in a humidified incubator at 37°C and 5% CO 2 . Cells were passaged by scraping cells from the flask surface, centrifuging and resuspending in new growth media. 5 x 104 cells/well were plated in DMEM + 10% horse serum in a 96 well plate 24 hours before the assay and incubated as above.
  • MHV-S (ATCC VR-766TM) was used to inoculate NCTC Clone 1469 cells at a moi of about 1.0 following published procedures (Leibowitz et al., 2011). Isolated virus was stored at -80°C in 1.0 ml aliquots. Virus titer was determined using the endpoint dilution procedure to obtain the TCID 5 o on the NCTC Clone 1469 cells. Suspension Test Laundry Complete, Lot 05062020-LC-A, was diluted at a ratio of 4.69 ml to 250 ml with ultrapure water. All tests contained 0.03% bovine serum albumin (BSA) as a clean interfering substance.
  • BSA bovine serum albumin
  • Tube A Virus Titer: 0.1ml stock virus, 0.1ml 0.3% BSA, 0.8ml PBS(phosphate buffered saline) Tube B: Product Test: 0.1ml stock virus, 0.1ml 0.3% BSA , 0.8ml diluted Laundry Complete Tube C: Cytotoxicity Control: 0.1ml DMEM +2% horse serum (DMEM-2), 0.1ml 0.3% BSA, 0.8ml diluted Laundry Complete Tube D: Virus killing control: 0.1 ml stock virus, 0.1ml 0.3% BSA, 0.2ml 1.4% Formaldehyde All tubes were incubated for 15 minutes at 21.8°C, 52% relative humidity.
  • the virus TCID 5 o (log 10) was determined to be 7.0
  • the virus TCID 5 o (log 10) after treatment with Laundry Complete was 3.0.
  • the log difference between them was 4.0 indicating 99.99% of the virus was killed.
  • Dimethyloctadecyl (3-trimethoxysilyl) propyl ammonium chloride is known to covalently bind to textile fabrics and will maintain a presence for up to 25 industrial washes.
  • Dimethyloctadecyl (3-trimethoxysilyl) propyl ammonium chloride is also known to be bacteriastatic and fungistatic but not bactericidal, viricidal nor fungicidal.
  • the Laundry Complete formulation containing ammonium chloride quats, and polyhexamethylene biguanide hcl form a polymeric nano composite matrix which imparts antiviral traits which are persistent.
  • SARS CoV-2 CDC surrogate namely a Murine Hepatitis virus, MHV-S.
  • MHV-S was grown in a mouse liver cell line, NCTC clone 1469 Isolated virus was incubated with a piece of fabric treated with My Shield Laundry Complete (Treated on December 16, 2019 and kept in a sterile container since then).
  • Controls were untreated fabric pieces of the same size. After incubation with the virus for 15, 30 or 60 minutes the samples were neutralized with D/E broth, vortexed to remove the virus from the fabric and passed over a Sephadex LH-20 column to remove potential cytotoxic substances. Serial dilutions of the column eluates were used to inoculate NCTC clone 1469 cells in a 96 well plate to determine the TCID 50 for the virus at each time. After 14 days the wells were examined for cytopathological effects (CPE) in the cells and scored accordingly.
  • CPE cytopathological effects
  • a neutralizer cytotoxicity control run separately, showed no CPE at any dilutions of the D/E broth.
  • Formaldehyde killed all cells to the 10-4 dilution.
  • the persistence of the virucidal activity of the My Shield Laundry Complete was evident even after more than 200 days with at least 99% kill of virus after only an hour of contact with the fabric, and nearly 97% kill after only 30 min.
  • EXAMPLE VI In a further experiment with actual wild strain SARS CoV-2 done in a BSL3 laboratory, a cotton textile product treated with Laundry Complete on Feb 6, 2021. The sample was inoculated and tested 53 days later on April 5-9, 2021.
  • a test suspension of the SARS-CoV-2 virus was inoculated onto My-Shield Laundry Complete coated fabric #06302020-LC-A (100 % cotton) and its respective control fabric (100 % cotton) surface.
  • the surfaces loaded with virus inoculum were maintained at specified temperature (25° C ⁇ 1° C) for a contact period of 2 hours.
  • At the end of the contact time remaining infectious virus particles were recovered individually from onto My-shield Laundry Complete #06302020-LC-A coated fabric specimen and its respective control fabric specimen by washing the surfaces followed by vortex and agitation in neutralizing medium. Quantification of recovered surviving organisms (infectious virus particles) was done by plaque assay. As prescribed in guideline assay was performed in triplicate using 3 test specimen for each step.
  • the antiviral efficacy of My-shield Laundry Complete coated fabric Lot #06302020- LC-A tested after 53 days of coating onto the specimen (100 % cotton fabric) has a GOOD EFFECT' as per the antiviral performance standard against SARS-CoV2.
  • the results indicates that My-shield Laundry Complete treated fabric specimen Lot #06302020-LC-A exhibited virucidal activity against SARS-CoV2 virus. No live infectious SARS-CoV-2 virus particles were retained on My-shield Laundry Complete treated fabric specimen Lot #06 A panel than that of respective untreated control specimen after contact time of 2 hours.

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EP21822880.7A 2020-06-12 2021-06-14 Textilbehandlungsmittel Pending EP4165152A1 (de)

Applications Claiming Priority (2)

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US202063038635P 2020-06-12 2020-06-12
PCT/US2021/037298 WO2021253015A1 (en) 2020-06-12 2021-06-14 Textile treatment compositions

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