WO2007030117A2 - Revetement de surface multifonctionnel et autodecontaminant - Google Patents

Revetement de surface multifonctionnel et autodecontaminant Download PDF

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Publication number
WO2007030117A2
WO2007030117A2 PCT/US2005/032091 US2005032091W WO2007030117A2 WO 2007030117 A2 WO2007030117 A2 WO 2007030117A2 US 2005032091 W US2005032091 W US 2005032091W WO 2007030117 A2 WO2007030117 A2 WO 2007030117A2
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WO
WIPO (PCT)
Prior art keywords
coating
group
ethoxy
biocidal
hydrophilic
Prior art date
Application number
PCT/US2005/032091
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English (en)
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WO2007030117A3 (fr
Inventor
James H. Wynne
Joanne M. Jones-Meehan
Arthur W. Snow
Leonard J. Buckley
Original Assignee
The Government Of The United States Of America, As Represented By The Secretary Of The Navy
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US11/183,305 external-priority patent/US7339015B2/en
Application filed by The Government Of The United States Of America, As Represented By The Secretary Of The Navy filed Critical The Government Of The United States Of America, As Represented By The Secretary Of The Navy
Priority to MX2007005284A priority Critical patent/MX2007005284A/es
Publication of WO2007030117A2 publication Critical patent/WO2007030117A2/fr
Publication of WO2007030117A3 publication Critical patent/WO2007030117A3/fr

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Classifications

    • 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
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
    • C09D5/1612—Non-macromolecular compounds
    • C09D5/1625—Non-macromolecular compounds organic
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4

Definitions

  • the invention is generally related to the fields of biocides and biocidal and/or spo ⁇ cidal coatings
  • Decontamination and neutralization of surfaces from bacteria and spores is a complex process that involves multiple technologies and various approaches, depending on the nature and extent of contamination
  • biocides and antiviral coatings there are very few that claim to be effective as spo ⁇ cides
  • decontaminating agents and solvents used to prepare them must be mixed onsite and applied for effective use
  • anthrax spore The ability to decontaminate chemically-resistant, coated painted surfaces inoculated with anthrax spores is extremely important
  • the anthrax spore is the most persistent of all biowarfare agents To kill them, the most potent biocides/spo ⁇ cides must be employed Irradiation is frequently necessary and often ineffective due to the robustness of dormant or weaponized spores Such spores may remain dormant for decades, yet are easily com erted into the harmful or lethal vegetative form within minutes under ideal c jnditions
  • the cell wall of a typical 1-2 ⁇ m vegetative bacterium is very complex, with multiple layers outside the cytoplasmic membrane
  • the structure of the cell wall consists of an outer glycocalyx capsule layer atop of an S- layer, peptidoglycan layer, and finally a plasmic membrane protecting the nucleus
  • any biocide must be able to penetrate through this 40 run outer wall consisting of layers such as glycocalyx, 5-layer,
  • Quaternary ammonium, pyridiniuTi, and phenolic compo ind « are ⁇ i to possess biocidal act; /if, and have been used in a variety of applications and numerous commercially available products These compounds have not only tound utility as biocides but also as phase transfer catalysts and mobility systems designed to aid in the drug ⁇ delivery processes They have also been reported to possess antiseptic properties
  • the invention comprises a coating, comprising an adhesive hydrophilic polymer and an amphiphihc additive
  • the amphiphihc additive comprises a hydrophilic chain, a biocidal functional group bonded to the ⁇ ⁇ hydrophilic chain, and a hydrophobic moiety bonded to the hydrophilic chain or to the biocidal functional group
  • the invention further comprises a method of forming a biocidal surface comprising providing an article, and coating the article with the above coating
  • the invention further comprises a compound comprising the formula
  • H R is selected from the group consisting of
  • X is a halogen
  • m and n are independently selected positive integers MODES FOR CARRYING OUT THE INVENTION
  • the coating may be a multifunctional surface modifier
  • the coatings may have persistent bacte ⁇ cidal/bio-inhibitory activity coupled with a biocidal self-concentrating capability at polymer coating surfaces
  • the approach utilizes a hydrophobic/hydrophihc balance, such that the bactericidal functional group may self-orient toward the surface/air interface while retaining enough hydrophilic characterto be compatible with the hydrophilic resm system and promote moisture retention
  • the approach makes use of a hierarchical four-component molecular system incorporated as an additive into selected polyurethane resin systems
  • the biocidal functional group is responsible for death of the cell
  • the hydrophobic moiety is responsible for orientation of the biocide functionality toward the surface of the over-coating
  • the hydrophilic chain functions to attract and retain moisture and for compatibility with the hydrophilic resin system This may function in conjunction with the selected resm system to provide the needed moisture to germinate spores into the vegetative state
  • the adhesive polymer serves as a hydrophilic
  • the invention is a coating compnsing an adhesive polymer and an amphiphilic additive as stated above
  • the coating may be applied to the surface of an article to give the surface biocidal properties
  • the adhesive polymer facilitates binding to a substrate
  • Suitable adhesive hydrophilic polymers include, but are not limited to, polyurethanes, polyurethane hydrogels such as HYDROTHANETM (CardioTech International, Inc,), epoxies, polyesters, and polyacrylates No particular minimum level of adhesiveness or hydrophihcity is required
  • the polymer need only adhere to a surface to be coated to a degree suitable for the manner in which the coated article is to be used
  • the polymer need only be hydrophilic enough to serve as a moisture reservoir for spore germination and to concentrate the amphihphilic biocidal additive at the surface
  • the term "adhesive hydrophilic polymer” includes single polymers and combinations and mixtures of two or more polymers
  • the hydrophilic chain of the amphiphilic additive is generally present in order to maintain the additive as part of the coating, through its attraction to the polymer, though it is not limited to such use
  • the hydrophilic chain may incorporate into the polymer by a variety of methods such as hydrogen bonding, covalent bonding, ionic coordination, or chain entanglement
  • the hydrophilic chain may also function as an attractive area for moisture absorption and as a promoter of germination
  • the hydrophilic chain may form a layer between the adhesive polymer and the bio'cidal group/hydxoph ⁇ bic moiety
  • the hydrophilic layer may include of several factors, such as physical or chemical bonding to an adhesive polymeric backbone, providing a source of moisture to promote the conversion from spore to vegetative bacterial cell, providing germinants to promote the conversion from spore to vegetative state, providing nutrients to promote the conversion from spore to vegetative state, attachment to a biocide functionality that will self-o ⁇ entate towards the surface, and attachment to a biocid
  • hydrophobic moiety is generally present, though it is not limited to such use, in order to orient the additive such that the biocidal group is preferentially near or at the surface of the coating, thus allowing the biocidal component to be at the surface of the coating and not buried within the polymeric layer No particular minimum level of hydrophobicity is required
  • Suitable hydrophobic moieties include, but are not limited to, alkyl groups, including linear alkyl groups having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms
  • the additive may contain a single moiety or multiple moieties that are the same or different, and the coating may contain two or more additives containing the same or different moieties
  • the biocidal functional group is generally present in order to kill or be damaging to bacteria that come in contact with the coating, though it is rot limited to such use Suitable biocidal groups include but ⁇ e not limited to, quaternary ammonium salts, py ⁇ dimum salts, and phenols
  • the addi'ive may contain a single biocidai g ⁇ oup or multiple biocidal groups that are the same or different, and the coating may ccntain two or more additives containing the same or different biocidal groups Suitable amounts of the amphiphilic additive or of the biociddl functional group include, but are not limited to, up to 5% or up to 1% by weight of the coating, such as 0 5% to 1%
  • the amphiphilic additive may have the following structure ⁇ _ ( O-CH 2 -CH 2 ) n -R-(CH 2 ) m -CH 3 Y is CH 3 or H R is selected from the group consisting of
  • X is a halogen, such as Cl, Br, or I
  • m is an integer from 1 to 17
  • n is an integer from 1 to 8
  • Y-(O-CH 2 -CH 2 ), is the hydrophilic chain
  • (CH 2 ) m -CH 3 is the hydrophobic moiety
  • R is the biocidal group
  • the three R groups are, respectively, a quaternary ammonium salt, a py ⁇ dimum salt, and a phenol
  • the coating may comprise more than one of these compounds having more than one value for m, n, or both m and n, such that the coating as a whole has a non-integer average value for m and/or n
  • the coating comprises a germinating agent in addition to the amphiphilic additive
  • the germinant is generally present in order to stimulate conversion of a bacterium from spore form to vegetative form, though it is not limited to such use
  • An example of such a bacteria is Bacillus anthracis
  • the biocidal group may not have any effect on a spore, but once the germinating group causes the conversion, the biocidal group may act on the bacteria
  • Suitable germinating agents include, but are not limited to, L-alamne and L- methiomne More than one germinating agent may also be present in the coating
  • Suitable amounts of the germinating agent include, but are not limited to, up to 5% or up to 1% by weight of the coating.
  • the germinating coating may also comprise a nutrient.
  • the nutrient is generally present to support development of the bacteria from the spore to the vegetative state. Suitable nutrients include, but are not limited to, Luria broth, and/or Yeast Extract and the compounds shown below. More than one nutrient may also be present in the coating. Suitable amounts of the nutrient include, but are not limited to, up to 5% or 1% by weight of the coating.
  • Features may include the ability for deposition as a polymeric thin film coating, controlled surface morphology/composition, promotion of spore germination, and bactericidal action. It involves the complex chemical and biological interactions acting across two dynamic interfaces or inter-phases between the bacteria/spore and the polymer coating.
  • the concept for self-decontaminating surfaces is applicable to other bioagents besides Bacillus anthracis spores, such as Yersinia pestis (plaque) and Francisella tularensis (tularemia), as well as other pathogenic bacteria.
  • the coating or additive may be applied to a variety of surfaces to function as a self-decontaminator and function as a biocide, sporicide, and an antiviral agent.
  • Several potential uses include chili Iren ' s toys, doorknobs, food preparation surfaces, air handling ducts, military equipment, military vehicles, public transportation surfaces, and other areas that are easily contaminated or areas that are in high risk of biological terrorist attacks.
  • the coating may facilitate decontamination in enclosed or field areas.
  • Possible advantages may include eliminating the need for caustic chemicals, caustic sporicides, radiation, or precise environments to rid a surface of spores.
  • This self-decontaminating coating or additive can allow for germination due to the presence of nutrients, germinants (including cogerminants), moisture, and biocidal functionality all incorporated at the surface of the coating and, thus, may be contacted by spores landing on the surface.
  • the coating may be constantly active and may require no activation or special control of atmospheric conditions.
  • Another embodiment is compounds having the structure shown above, where m and n are independently selected positive integers.
  • This embodiment includes mixtures of more than one such compounds having different values for m, n, or both m and n. Examples are shown below as well as example synthetic schemes. Suitable values for m are 1 to 17 and for n are 1 to 8, both including all numbers in between. This embodiment also includes mixtures of these compounds having more than one value for m, n, or both m and n.
  • biocidal functional groups and hydrophobic-hydrophihc substructures may each be varied independently
  • the , minimum oxyethylene chain length that afforded the maximum effectiveness was incorporated into the selected resin s> stems
  • the minimum length was desirable in an attempt not to mask t!ie hydrophobic substituent on the biocide, which dictated biocidal orientation within the coating
  • One of the many possible functional groups most suitable for incorporation into the resin systems described makes use of the acrylate moiety
  • the ability to retain the option to functionahze the hydrophilic chain with an acrylate may require modification to the synthetic approach (i e , este ⁇ f ⁇ cation) of the initial starting reagent within the reaction scheme
  • Germinant/nut ⁇ ent selection promoting vegetation of dormant anthrax spores is a very complex procedure because Bacillus anthracis does not rely on a single signal to promote spore germination Receptor proteins on the spore's membrane bind to ring-shaped or aromatic structures on certain amino acids (building blocks 5 of proteins) and purine ⁇ bonucleosides (building blocks of DNA and RNA) Small molecules or germinants have been reported to trigger spore germination for various bacterial spores (Clements et al , J Bacteriol 1998, 180, 6729, McCann et al , Lett Appl Microbiol 1996, 23, 290, Rossignol et al , J Bacteriol 1979, 138, 431, Rossignol et al , Biochem Biophys Res Commun 1979, 89, 547, Vary et al , J Bacteriol 1968, 95, 1327, Mock et al , Annu Rev
  • a series of antimicrobial testing and results indicate success A series of Gram-positive and Gram- negative bacteria were tested by four test methods (live/dead bacterial viability staining, disk diffusion test, tube ⁇ dilution method with neutralization agent to quench residual biocide activity and coated glass slide)
  • the following Gram-positive bacteria were used in the biocide tests Bacillus anthracis Sterne strain, Bacillus subtihs Enter ococcus faecalis, Staphylococcus aureus and Staphylococcus epidermidis
  • the following Gram-negative bacteria were used in the biocide tests Escherichia coh, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella typhimunum, Enterobacter cloacae, Proteus vulgaris, and Serratia marcescens
  • the prescreening of a O series of model biocide compounds was very successful in killing vegetative bacterial cells for all functionalities of interest
  • the approach of the present invention is designed to accelerate spore germination by the addition of known cogerminants for Bacillus anthracis such as L-alamne + L-amino acids (trp, tyr, pro, his), mosine with aromatic and non-aromatic L-amino acids (trp, tyr, phe, his, pro, phe, ser, val, ser) (Ireland et al , Medicine at 5 Michigan 2002 4 12, Ireland et al , J Bacteriol 2002 184 1296-1303)
  • the following cogerminants may be added to the coating system poly L-alanine, poly-L-tryptophan (various molecular weights), poly-L-tyrosine (various molecular weights), poly-L- amino acid peptides, inosine, ATP, etc Addition of pigments, fillers, polyester, amides, poly L-alamne, Yeast Extract, Luna Broth
  • Results employing commercial mixtures of germinants e g , Luna Broth (LB)
  • a mixture consisting of yeast extract, tryptone and sodium chloride has shown success, when employed in 0 1-20% (w/w) concentrations within the hydrophilic resin system.
  • Yeast extract with various L-arrnno acids i.e., L-alanine, L-methionine, etc.
  • L-alanine i.e., L-alanine, L-methionine, etc.
  • Screening may be conducted employing a variety of amino acids, heterocyclics, and components of - 1 commercial growth media.
  • the rapid screening and down selection from an extensive list of the germinants may allow for rapid optimization.
  • the germinants may be ranked and down-selected according to time dependence for germination The more effective germinant candidates have demonstrated the minimum effective concentration required for the desired response within the resin system. After selection in the test resin system, the germinants were then optimized for the final selected resin coating system. 0
  • Example 1 5 General procedure for preparation of methoxy terminated quaternary ammonium salts - In a 20 mL round bottomed flask equipped with reflux condenser and a positive flow of nitrogen were placed a tertiary amine (6 36 mmol), a bromo-ethyleneglycol monomethyl ether (6.36 mmol), and absolute ethanol (17.49 mmol). The solution was heated in an 83°C oil bath for 24 hr. The resulting solution was allowed to slowly cool to RT and concentrated under reduced pressure. The resulting thick yellow oil was titrated with petroleum ether (2 x 3 mL), " and placed under vacuum to remove trace solvent. The resulting product was dissolved in 2 mL of EtOH with vigorous stirring and then cooled to -30 0 C to result in crystallization of the desired product A second crop of equal purity may be recovered by recrystalhzation of the mother liquor.
  • Example 2 5 Characterization of methoxy terminated quaternary ammonium salts - Hexyl-[2-(2-methoxy- ethoxy)-ethyl]-dimethyl-ammonium bromide: FTIR: 3013, 2954, 2921, 2878, 1463, 1253, 1194 cm "1 1 H NMR (CDCl 3 ): 3.99-3.92 (dd, 4H), 3.72-3.58 (m, 4H), 3.54-3.51 (m, 2H), 3.42 (s, 6H), 3.36 (s, 3H), 1.78-1.74 (m, 2H), 1.34-1.31 (m, 6H), 0.90 (t, J I, 3H) ⁇ ' 3 C NMR (CDCl 3 ): 71.4, 70 3, 65.7, 64.9, 62.8, 58.8, 58.0, 51.8, 31 1, 25 7, 22.7, 22 3, 13.7 ⁇ .
  • Example 6 Characterization of hydroxyl terminated quaternary ammonium salts - Octyl-(2-(2-hydroxy- 0 ethoxy)-ethyl)dimethylamrnonium chloride: FTIR. 3279, 3009, 2954, 2921, 2858, 1467, 1364, 1126, 1071, 971, 892 cm 1 .
  • the resulting solution was allowed to cool to room temperature, concentrated usmg the rotary evaporator.
  • the resulting oil was eluted through a silica gel column employing a Hexane/EtOAc (1 :1) solvent system. The desired product eluted in the first fraction.
  • Example 10 Preparation of l-hexyl-4-(2- ⁇ 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy ⁇ -ethoxy)-pyridinium bromide — Pyridin-4-ol (1.50 g, 15.77 mmol) and toluene-4-sulfonic acid 2- ⁇ 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy ⁇ -ethyl ester (5.62 g, 19.71 mmol) were combined in a 50 mL round bottomed flask equipped with condenser, magnetic stir bar, and a positive flow of nitrogen. The solution was heated in a 100 0 C oil bath for 24 hrs.
  • the solution was then cooled and placed on a vacuum line at 1 mmHg and heated at 80 0 C for 6 hrs to removed residual starting materials.
  • the by-product was removed via washing with deionized water (3 x 15 mL) to afford 4-(2- ⁇ 2-[2-(2-methoxy- ethoxy)-ethoxy]-ethoxy ⁇ -ethoxy)-pyridine.
  • the product may be subsequently purified employing column chromatography techniques at this point or may proceed directly to the addition of 1-bromohexane (3.90 g, 23.66 mmol) in 25 mL tetrahydrofuran.
  • Antimicrobial testing - Live/dead bacterial viability staining was employed This is a two-color fluorescence assay of bacterial viability, which provided results in minutes This is a quantitatively method used to distinguish live and dead bacteria in minutes even in a mixed population of bacterial types SYTO-9 green fluorescent nucleic acid stain bacteria with intact membranes stain fluorescent green, excitation/emission maxima are 490/635 run Disk diffusion test, tube dilution method with neutralizing agent to quench residual activity (results shown in Table 1) and coated glass slides were the primary methods of evaluating model compounds A variety of gram-positive and gram-negative bacteria were tested A few of the Gram + utilized included Bacillus anthracis Sterne strain, Bacillus subtihs, Enterococcus faecalis, and Staphylococcus aureus Gram - utilized included Escherichia coh, Klebsiella pneumoniae, Pseudomonas aeruginosa, Salmonella typhimun
  • Quaternary ammonium biocides were subjected to minimum inhibitory concentration (MIC) studies for effectiveness comparisons (Table 2) Two Gram-positive bacteria (S aureus and B. anthracis Sterne strain), were employed along with two Gram-negative bacteria (Escherichia coh and Salmonella typhimunum) In all cases, those biocides possessing the octyl alkyl functionality were more effective antimicrobials than the corresponding analogs possessing the hexyl group The biocides possessing the hexyl moiety appeared to be more effective against Gram- negative versus Gram-positive bacteria, while those possessing the octyl moiety showed a lower MIC for Gram- positive bacteria versus Gram-negative bacteria Xhe compa ⁇ son study of hydroxyl-terminated biocides (entries 9 and 10) with the corresponding methoxy terminated analogs (6 and 2) respectively, showed similar responses The hydroxyl terminated octyl de ⁇ vative (9) was more effective than the corresponding hexyl

Abstract

L’invention concerne un revêtement comprenant un polymère hydrophile adhésif et un additif amphiphile. L’additif amphiphile comporte une chaîne hydrophile, à laquelle est relié un groupe fonctionnel biocide, et une fonction hydrophobe reliée à la chaîne hydrophile ou au groupe fonctionnel biocide. L’invention concerne également un procédé de formation d’une surface biocide, utilisant un article et l’enduisant dudit revêtement. L’invention concerne en outre un composé de formule (I) : entiers positifs choisis de manière indépendante.
PCT/US2005/032091 2004-10-28 2005-09-12 Revetement de surface multifonctionnel et autodecontaminant WO2007030117A2 (fr)

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Application Number Priority Date Filing Date Title
MX2007005284A MX2007005284A (es) 2004-10-28 2005-09-12 Revestimiento de superficie autodescontaminante multifuncional.

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US11/183,305 2005-07-14
US11/183,305 US7339015B2 (en) 2004-10-28 2005-07-14 Multifunctional self-decontaminating surface coating

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WO2007030117A3 WO2007030117A3 (fr) 2007-05-31

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030108957A1 (en) * 2002-07-19 2003-06-12 The Wistar Institute Of Anatomy And Biology Biocidal molecules, macromolecular targets and methods of production and use
US20030114342A1 (en) * 2001-09-20 2003-06-19 Lonza Inc. Compositions comprising quaternary ammonium compounds and dendritic polymers with antimicrobial activity
US6656919B1 (en) * 2002-01-11 2003-12-02 Clarence L. Baugh Method and a product for the rapid decontamination and sterilization of bacterial endospores
US6838491B1 (en) * 1998-06-11 2005-01-04 Johnson & Johnson Vision Care, Inc. Biomedical devices with hydrophilic coatings
US20050008671A1 (en) * 2003-07-10 2005-01-13 Medtronic Minimed, Inc. Methods and compositions for the inhibition of biofilms on medical devices

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6838491B1 (en) * 1998-06-11 2005-01-04 Johnson & Johnson Vision Care, Inc. Biomedical devices with hydrophilic coatings
US20030114342A1 (en) * 2001-09-20 2003-06-19 Lonza Inc. Compositions comprising quaternary ammonium compounds and dendritic polymers with antimicrobial activity
US6656919B1 (en) * 2002-01-11 2003-12-02 Clarence L. Baugh Method and a product for the rapid decontamination and sterilization of bacterial endospores
US20030108957A1 (en) * 2002-07-19 2003-06-12 The Wistar Institute Of Anatomy And Biology Biocidal molecules, macromolecular targets and methods of production and use
US20050008671A1 (en) * 2003-07-10 2005-01-13 Medtronic Minimed, Inc. Methods and compositions for the inhibition of biofilms on medical devices

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