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WO2012065610A1 - Procédé et substrat avec revêtement « quat » - Google Patents

Procédé et substrat avec revêtement « quat » Download PDF

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Publication number
WO2012065610A1
WO2012065610A1 PCT/DK2010/050312 DK2010050312W WO2012065610A1 WO 2012065610 A1 WO2012065610 A1 WO 2012065610A1 DK 2010050312 W DK2010050312 W DK 2010050312W WO 2012065610 A1 WO2012065610 A1 WO 2012065610A1
Authority
WO
WIPO (PCT)
Prior art keywords
pei
substrate
quaternary ammonium
anpah
antimicrobial
Prior art date
Application number
PCT/DK2010/050312
Other languages
English (en)
Inventor
Mikkel Vestergaard Frandsen
Michael Stanley Pedersen
Sebastien Gouin
Alexander M. Klibanov
Bryan Boen Hsu Hsu
Original Assignee
Vestergaard Frandsen Sa
Massachusetts Institute Of Technology
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 Vestergaard Frandsen Sa, Massachusetts Institute Of Technology filed Critical Vestergaard Frandsen Sa
Priority to PCT/DK2010/050312 priority Critical patent/WO2012065610A1/fr
Publication of WO2012065610A1 publication Critical patent/WO2012065610A1/fr

Links

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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0208—Tissues; Wipes; Patches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • 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
    • D06M10/00—Physical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. ultrasonic, corona discharge, irradiation, electric currents, or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/04—Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/08—Organic compounds
    • D06M10/10—Macromolecular compounds
    • 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
    • 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
    • D06M2400/00—Specific information on the treatment or the process itself not provided in D06M23/00-D06M23/18
    • D06M2400/01—Creating covalent bondings between the treating agent and the fibre

Definitions

  • the present invention relates to binding of quaternary ammonium to a substrate, for example a fabric, in order to render the substrate antimicrobial.
  • International Patent Application Wo2000/033778 by Batich et al. assigned to Quick- Med discloses a superabsorbent polymer matrix with an enhanced surface area and an antimicrobial compounds coupled by non-siloxane bonds, for example covalent bonds, to the polymer matrix, the antimicrobial compounds being quaternary ammo- nium, for example.
  • International Patent Application Wo2003/039602 by Batich and assigned to Quick-Med discloses a substrate, for example a wound dressing, having a quat coating covalently bound to the substrate.
  • International Patent Application Wo2007/24972 by Liesenfeld et al. assigned to Quick-Med discloses a wound dressing with a non-leachable antimicrobial, for example quaternary ammonium, and a releasable agent, for example doxycycline.
  • Co- valent binding of biological entities on a polymer surface is disclosed in US 4,716,122 by Schaefers assigned to Organogen, where aryl-azide groups are used to covalently bind reaction components of immunological reactions to a carrier material, for example consisting of a synthetic resin, especially surface-treated polyethylene.
  • the preferred provider for such aryl-azide groups is SANPAH.
  • US 2009/117166 by Myung et al discloses antibody binding to a polymer surface through a SANPAH-Collagen- SANPAH intermediate layer.
  • US 2009/081797 by Fadeev discloses a polymer surface which has been plasma-treated to form functional groups, which form covalent bonds with a conjugate to which a biologically active compound is attached.
  • An option for the conjugate is SANPAH.
  • fluorescin quaternary ammonium compound
  • This object is achieved by the following method for providing a coating on a sub- strate, where the coating comprising a PEI-based polymer having antimicrobial quaternary ammonium.
  • the method comprises
  • the method comprises reacting the photoreactive coupling agent with the PEI before the methylation process.
  • the photoreactive coupling is a covalent coupling.
  • the method comprises dodecylation of the quaternised PEI before methylation.
  • the method comprises binding a protecting agent to some of the quaternary ammonium sites of the PEI before dodecylation and removing the protecting agent after dodecylation.
  • a potential protecting agent is Trityl, although other agents are possible.
  • the antimicrobial polymeric quaternary ammonium has antimicrobi- ally active quaternary ammonium with three dodecyl groups.
  • the antimicrobially active quaternary ammonium has two dodecyl groups and one methyl group.
  • other combinations of alkyl groups may be part of the antimicrobial quaternary ammonium in the polymer.
  • ANPAH is used in a photochemical reaction as a coupling agent between the substrate and the antimicrobial polymeric quaternary ammonium.
  • ANPAH is 6-[4'-azido-2'-nitrophenylamino]hexanoyl and illustrated below.
  • the substrate is provided with the antimicrobial polymeric quaternary ammonium including the ANPAH and exposed to light. Although visible light would induce photochemical reaction, the binding is, typically, performed with UV irradiation of the coating on the substrate.
  • ANPAH is suited as a photochemical coupling agent, especially, when using a polyethyleneimine (PEI) based polymer.
  • PEI polyethyleneimine
  • the PEI can, optionally, be a branched PEI, for example implying a ratio of primary to secondary to tertiary amines of 1:2: 1.
  • An ANPAH-PEI polymer can be created, which may then be bound to the substrate with covalent attachment of the ANPAH on the substrate.
  • the ANPAH-PEI polymer is an N-alkyl-N-ANPAH-PEI polymer, especially, an N-alkyl-N-methyl-ANPAH-PEI polymer.
  • Such a polymer can be created by providing PEI, quaternising PEI, and using methylation of the quaternised PEI before photochemical coupling of the PEI to the substrate.
  • the method includes formation of PEI, for example by acid hydrolysis, quaternisation by dodecylation followed by methylation.
  • ANPAH Adding ANPAH to this scheme, a polymer is created of the form N-dodecyl-N-methyl- ANPAH-PEI.
  • the inclusion of the photo-reactive ANPAH in the polymer should be made before the methylation process, for example after the dodecylation process, because the methylation can have detrimental effect on the photoreactive process.
  • the active quaternary ammonium may have two methyl groups and one dodecyl group, which is an embodiment for an antimicrobial quat as described for a non-covalent binding in International Patent Application Wo2008/127416 by Haldar et al. assigned to MIT.
  • the photochemical reaction advantageously, involves a reaction between the ANPAH and hydroxyl groups of a substrate.
  • ANPAH is photochemical coupled to hydroxyl groups of the substrate.
  • ANPAH is provided by reacting SANPAH with PEI for creation of an ANPAH-PEI polymer, where the succinimidyl entity is split off during the reaction.
  • the PEI based polymer was branched, hydrophopbic, and poly- cationic.
  • Materials include cellulose materials, for example cotton or regenerated cellulose, as well as synthetic polymer, for example polyester, polyamide, acetate polymers, or polyolefins.
  • Examples of possible substrates include non-exclusively hard polymer surfaces, for example from medical devices, and soft surfaces including fabrics. Special application is found in antimicrobial clothing, towels, wipers, sheets, gauze, wound dressings, bandages, and air masks.
  • Examples of microbes against which such antimicrobial coatings can be used include bacteria, virus, and fungi, especially human pathogenic bacteria and viruses.
  • the types of counteracted bacteria include both Gram-positive as well as Gram-negative bacteria, such as Escherichia coli and Staphylococcus aureus.
  • the counteracted viruses include both enveloped virus, for example influenza viruses, as well as non- enveloped viruses, for example polio viruses.
  • the invention also comprises a method of cleaning skin and killing microbes, the method comprising providing a fabric coated with an antimicrobial polymeric quaternary ammonium according to the above, and contacting human skin with the fabric, for example under dry conditions, that is without wetting the fabric first. During contact, pathogenic microbes are picked up from the skin with the fabric and eliminated by contact with the antimicrobial polymeric quaternary ammonium in the fabric.
  • the invention comprises a method of cleaning skin and killing microbes, the method comprising providing a fabric coated with an antimicrobial polymeric quaternary ammonium covalently to a substrate with ANPAH as a coupling agent between the substrate and the antimicrobial polymeric quaternary ammonium, and contacting human skin with the fabric, during contact picking up pathogenic microbes from the skin with the fabric, and eliminating the microbes by contact with the antimicrobial polymeric quaternary ammonium.
  • the advantage of the fabric being capable of cleaning skin under dry conditions makes the fabric suitable for use in rural areas and under emergency situations, where the access to water is scarce.
  • the fabric could be used as a long-lasting cleaning wiper that reduces risks for spread of diseases.
  • Aspect 1 in that the coupling agent is ANPAH.
  • An example of a substrate is a fabric, the term fabric including microfibre textiles.
  • the antimicrobial polymeric quaternary ammonium is a polymer based on polyethyleneimine, PEI;
  • Aspect 3 optionally, reacting ANPAH with PEI and as a result creating an ANPAH- PEI polymer
  • the ANPAH-PEI polymer is an N-alkyl-N-methyl-ANPAH-PEI polymer
  • the method comprises providing PEI, quaternising PEI, and us- ing methylation of the quaternised PEI before photochemical coupling of the PEI to the substrate, for example, also reacting ANPAH with PEI before the methylation process;
  • the ANPAH-PEI polymer is an N-dodecyl-N-methyl- ANPAH- PEI polymer, for example, the method comprises dodecylation of the quaternised PEI before methylation.
  • the method comprises reacting ANPAH with PEI after dodecylation
  • the antimicrobial polymeric quaternary ammonium has antim- icrobially active quaternary ammonium groups with two dodecyl groups and one methyl group; alternatively, it may have two methyl groups and one dodecyl group;
  • the reacting of ANPAH with PEI comprises dissolving SANPAH and dissolving PEI and reacting the dissolved SANPAH with the dissolved PEI to form an ANPAH-PEI polymer;
  • the PEI based polymer is branched, for example hydrophopbic and/or polycationic, in addition;
  • the method comprises providing a substrate with hydroxyl groups and photochemical coupling the ANPAH to the hydroxyl groups of the substrate.
  • the initial purpose is also achieved with a substrate, for example a fabric, including microfibre textiles, the substrate having an antimicrobial coating, preferably produced by a method according to any of the above aspects, wherein the coating comprises antimicrobial polymeric quaternary ammonium bound covalently to the substrate with ANPAH as a coupling agent between the substrate and the antimicrobial polymeric quaternary ammonium.
  • the coating comprises an N-alkyl-N-methyl- ANPAH-PEI polymer, for example an N-dodecyl-N-methyl-ANPAH-PEI polymer.
  • the antimicrobial polymeric quaternary ammonium has antimicro- bially active quaternary ammonium groups with two dodecyl groups and one methyl group.
  • the synthesis procedure for the coating with the antimicrobial polymeric quaternary ammonium implies an initial protection step.
  • Trityl is protected by binding Trityl to some of the quaternary ammonium sites of the PEI, which can be illustrated by the following.
  • a branched polyethyleneimine, BPEI was used with a weight of 750 kDa, although the weight could also be different and is not limited to this specific number.
  • the following parameters for weight, amount, temperatures and durations of actions described in connection with a concrete experimental embodiment are exemplary but can be slightly modified.
  • BPEI was provided by 50 wt in water, why, as an initial step, it was dehydrated in a lyophilizer to provide dry BPEI.
  • An amount of 5.2g of this dry BPEI was dissolved in 25 mL anhydrous di- methylformamide under Ar.
  • An amount of 6 mL anhydrous dichloromethane was added.
  • An amount of 6 mL of 0.5M trityl chloride solution in anhydrous dichloromethane was drop- wise added at -10°C in a NaCl/ice water bath with a flushing of the generated HC1 gas with Ar.
  • the mixture was stirred overnight for about 12 hrs, allowing the ice bath to melt and return to room temperature.
  • the polymer precipitated overnight. Volatiles were removed under vacuum.
  • the final polymer was redissolved in methanol and subject of dialysis in 3.5kDa molecular-weight cutoff (MWCO) regenerated cellulose dialysis membrane (Spectrum Labs) against 2L methanol for at least 8hrs, repeated once more with fresh 2L methanol.
  • MWCO molecular-weight cutoff
  • the methanol was subsequently removed from the dialyzed polymer under vacuum to yield 4.5g of N-Tr-BPEI.
  • the N-Tr-BPEI of the previous step was subsequently subject to dodecylation.
  • An amount of l.Og of N-Tr-BPEI, 3.8g K2C03, 14 mL tert-amyl alcohol (dried over molecular sieves), and 17 mL 1-bromododecane were combined.
  • Using a connection to a condenser it was flushed and left with an Ar balloon, stirred at 95°C for 96 hrs, and then centrifuged at 6000 rpm for 30 min at room temperature to remove carbonate salts.
  • the supernatant was dialyzed against 2L of hexane for at least 8hrs, repeated once with fresh 2L hexane.
  • the final yield was 4.0g N,N-dodecyl,Tr-BPEI
  • the neutralized solution was dialyzed against 1L of dialysis solution for at least 8hrs, repeated once with fresh 1L of dialysis solution and then twice with 1L of fresh chloroform. From the dialyzed polymer, volatiles were removed under vacuum to yield 0.78g N-dodecyl-BPEI.
  • the coupling agent was introduced.
  • 0.75g of N-dodecyl-BPEI were dissolved in 5 mL of anhydrous dichloromethane to which 8.8 micro-liter of diisopropylethylamine was added as well as an amount of 50mg SANPAH dissolved in 5mL anhydrous dichloromethane.
  • the mixture was stirred in dark at room temperature for 1 hr followed by dialysis against 1L of dichloromethane overnight in the dark.
  • the solvent was removed under vacuum from the dialyzed polymer to yield is 0.63g of N,N-ANPAH,dodecyl-BPEI
  • N-dodecyl-N- methyl-N-ANPAH-BPEI was dissolved in dichloromethane and coated to a substrate with subsequent illumination by UV radiation for 10 minutes.
  • the method may also be used for a coating with antimicrobial quaternary ammonium in the polymer having two or only one dodecyl group.
  • other combinations of alkyl groups may be part of the antimicrobial quaternary ammonium in the polymer.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Textile Engineering (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Biomedical Technology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Biochemistry (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne un procédé de revêtement consistant à déposer un revêtement antimicrobien longue durée sur un substrat, par exemple un tissu, procédé dans le cadre duquel de l'ammonium quaternaire (quat) polymère antimicrobien est lié au substrat par couplage photochimique avec un agent, par exemple l'ANPAH. Ledit revêtement peut être déposé sur un tissu qui pourra ainsi être utilisé en vue d'un nettoyage à sec de la peau par exemple.
PCT/DK2010/050312 2010-11-18 2010-11-18 Procédé et substrat avec revêtement « quat » WO2012065610A1 (fr)

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PCT/DK2010/050312 WO2012065610A1 (fr) 2010-11-18 2010-11-18 Procédé et substrat avec revêtement « quat »

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10525614B2 (en) 2015-01-09 2020-01-07 Nano And Advanced Materials Institute Limited Built-in antimicrobial plastic resins and methods for making the same
WO2022203952A1 (fr) * 2021-03-22 2022-09-29 Polaroid Ip B.V. Compositions de revêtement antimicrobiennes
WO2024069491A1 (fr) * 2022-09-28 2024-04-04 Polaroid Ip B.V. Compositions de revêtement antimicrobiennes

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10525614B2 (en) 2015-01-09 2020-01-07 Nano And Advanced Materials Institute Limited Built-in antimicrobial plastic resins and methods for making the same
WO2022203952A1 (fr) * 2021-03-22 2022-09-29 Polaroid Ip B.V. Compositions de revêtement antimicrobiennes
WO2024069491A1 (fr) * 2022-09-28 2024-04-04 Polaroid Ip B.V. Compositions de revêtement antimicrobiennes

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