HK1101109B - Anti-microbial composition - Google Patents
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- HK1101109B HK1101109B HK07109160.8A HK07109160A HK1101109B HK 1101109 B HK1101109 B HK 1101109B HK 07109160 A HK07109160 A HK 07109160A HK 1101109 B HK1101109 B HK 1101109B
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This application is a divisional application of the invention patent application having filing date 20020102, application No. 02804949.7, entitled "antimicrobial composition".
The present invention relates to antimicrobial compositions and formulations comprising the microbial compositions.
Microorganisms can be found in many environments and are known to be hazardous to health due to microbial infections and contamination.
When microorganisms are present on the surface of a substrate, they can replicate rapidly and form colonies. Virtually all microorganisms replicate in this manner. Microbial colonies form a coating on the surface of a substrate, called a biofilm. Biofilms are more dangerous to health than individual microorganisms. Some microorganisms also produce polysaccharide coatings, making them more difficult to destroy.
Biofilms can be formed by a single bacterial species, but are generally composed of several bacteria, as well as fungi, algae, protozoa, debris, and corrosion products. In essence, biofilms can form on all surfaces exposed to bacteria and some water that is needed to carry out metabolic processes.
Biofilm formation occurs through three separate stages. These three stages are (i) adhesion or attachment, (ii) proliferation and (iii) biofilm differentiation.
Before stage (i) occurs, the microorganisms must be transferred to a surface. This can occur via brownian motion, sedimentation, activity transfer or chemotaxis with random contact with the surface. Once the microorganisms have been transferred to the surface, they begin to adhere to the surface due to, for example, Lifshitz-van der waals forces, acid-base interactions, and electrostatic forces between negatively charged microorganisms and positively charged regions.
The microorganisms subsequently secrete extracellular polymers, forming extracellular polymers consisting of polysaccharides, nucleic acids, amphoteric substances, humus and proteins. Extracellular polymers form the matrix that interconnects and binds together the microorganisms that are attached to the surrounding surface. Thus, the microorganisms are immobilized on a surface, which may be any type of substance such as metal, plastic, soil particles, medical graft material, and tissue.
Once immobilized on a surface, biofilm microorganisms undergo a variety of deleterious or beneficial reactions (according to human standards) depending on the surrounding environmental conditions. Accordingly, it is desirable to remove and/or destroy biofilm microorganisms on a surface.
Pasteurization has long been used to destroy microorganisms. In this method, the microorganisms are subjected to elevated temperature and optionally elevated pressure.
Microorganisms can also be removed from surfaces by simply washing and sanitizing the surface with fresh water or using soap or a simple detergent. Washing removes most of the microorganisms, but does not prevent the growth of any residual microorganisms.
Microorganisms can also be destroyed by contacting them with antimicrobial agents that are toxic to them. Many antimicrobial agents are known. For example bactericides, fungicides, algicides, yeasts and mildewicides are known. Antimicrobial agents are capable of destroying microorganisms present in a variety of environments, such as medical, industrial, commercial, household, and marine environments. Many known antimicrobial agents have been included in compositions for various applications and environments.
For example, EP-A-0233954 describes ｃA composition for treating solid materials to render them antimicrobial, hydrophilic and antistatic. The composition includes a silane-containing quaternary ammonium salt, an organopolysiloxane, and optionally an organic solvent.
EP-A-0206028 describes ｃA method for promoting plant growth. The method comprises administering a specific quaternary ammonium compound, which can be formulated as an aqueous solution.
EP-A-0181182 describes an emulsion comprising ｃA water, ｃA water-immiscible liquid, ｃA cationic silane and optionally ｃA co-surfactant.
WO-A-93/10209 describes A composition for disinfecting, sterilizing, cleaning and lubricating medical and dental instruments. The composition contains a water-soluble or water-dispersible disinfectant and/or bactericide, a surfactant and a water-soluble polymer having lubricating properties.
WO-A-92/21320 describes medicated shampoo compositions which contain an antimicrobial agent. The compositions include antimicrobial agents, chelating agents, and cleaning agents comprising fatty acid monoesters of polyhydroxy alcohols.
US-A-5244666 describes A liquid formulation for use as A preoperative skin wash or wound disinfectant. The formulation comprises a quaternary ammonium compound, a substituted phenol compound, water, and sodium lauryl sulfate.
JP-9175904 describes an agricultural composition comprising 1, 2-benzisothiazolin-3-one, dimethylpolysiloxane, water and N-tert-butyl-N' - (4-ethylbenzoyl) -3, 5-dimethylbenzohydrazide.
Known antimicrobial agents and compositions containing these agents are capable of destroying microorganisms by a variety of different mechanisms.
Chlorinated compounds such as hypochlorite (bleach) can act as antimicrobial agents. Conventional bleaching agents include sodium hypochlorite. Sodium hypochlorite decomposes to produce chloride and chlorate. Chlorate is highly toxic to living organisms.
Although bleaches can be used to destroy a wide variety of microorganisms, they generally work only for a short time. This is because their effectiveness decreases rapidly upon decomposition. Thus, bleaching agents do not provide long-term antimicrobial passive control and sanitization. By "passive control" is meant that the substrate, by virtue of its inherent properties, independently resists microbial infection, thus eliminating the need for a cleaning regimen that is effective in controlling microorganisms. In addition, bleaching agents can decompose to produce chlorine gas, which is known to be harmful to the environment. Therefore, the use of chlorine-containing compounds should be avoided as much as possible.
Other known antimicrobial agents include phenol and its compounds, arsenic and arsenic salts. Examples of useful phenolic compounds include polychlorinated biphenols such as triclosan. Other known common antimicrobial agents include organic and inorganic salts of heavy metals such as silver, copper or tin. For example, colloidal silver may be used.
Phenolic compounds are generally highly toxic to humans and animals, as well as to microorganisms. Their handling is hazardous and therefore requires specialized handling, handling and equipment to safely handle these antimicrobial agents. It is also difficult to handle if the antimicrobial agent is strongly acidic or basic. Thus, the manufacture and disposal of compositions containing such antimicrobial agents is also a problem. There are also problems associated with the use of highly toxic antimicrobial agents, especially in consumer materials where it is difficult to ensure that they are used for their intended purpose.
Herein, unless otherwise indicated, "toxicity" refers to toxicity to a complex organism such as a mammal. Therefore, the explanation of "toxic" can be referred to.
Phenolic and heavy metal based antimicrobials are generally only effective against certain microorganisms such as fungi. Thus, its application is limited because it is not effective against various microorganisms. In addition, some antimicrobial agents, such as biphenol, do not remain effective for long periods of time because of their volatility and do not remain on the surface to which they are applied.
Once the antimicrobial agent and/or its decomposition products enter the environment, it can affect the health of the living being it does not affect. In addition, antimicrobial agents and their decomposition products are generally very stable and can cause long-term environmental problems. For example, metal salts produce toxic leachates (rinsates), which are toxic to aquatic organisms. Once a toxic substance enters the environment, it does not readily decompose and can cause long-term problems or unknown results. For example, colloidal silver, tributyltin, and diuron can remain in the environment for extended periods of time. The oxidation of polychlorinated biphenol compounds produces dioxins, which are harmful to the environment.
Other antimicrobial agents currently in use include antibiotic-type compounds such as penicillin. Antibiotics disrupt the biochemistry within the body of a microorganism, for example, by selectively diluting a solution to destroy or inhibit the growth of a harmful microorganism.
Although effective, it is presently believed that antibiotics may selectively allow development of resistant strains of the species on which they act. These resistant strains can replicate unimpeded using known antibiotics. Thus, there is increasing interest in the widespread and uncontrolled use of antibiotics in a wider environment, as opposed to controlled use in medicine, with significant long-term risks. Thus, antibiotics are considered unsuitable for general use in non-medical environments.
There is also a risk that resistant strains can be present with other types of antimicrobials that have biochemical effects. For example, "multidug Effiux Pumps and Triclosartan resistance in Pseudomonas aeroginosa" 100 in Chunacheen et althGeneral Meeting of the American society for Microbiology, May 21-25, LA; "Unique Mechanism of triclosan Resistance Identified in Environmental Isolates" of Meade et al, 100thGeneral meeting of the American Society for Microbiology, May 21-25, LA; "An Evaluation of biological-containing Materials for the surface catalysis-resistance and Other Properties" 100 of Suzangar et alth General MeetiTriclosan resistance is discussed in ng of the American Society for Microbiology, May 21-25, LA.
Thus, there is a need for an antimicrobial composition that is effective against a wide variety of microorganisms for a long period of time and that can be used safely and conveniently.
According to one aspect of the present invention there is provided an antimicrobial composition comprising (i) a first compound having a high surface tension of from 20 to 35mN/m, (ii) a second compound having a low surface tension of from 8 to 14mN/m, (iii) a first antimicrobial agent and (iv) a polar solvent, the composition being primarily for use in preventing the formation of microbial colonies on the surface of the composition.
The antimicrobial compositions of the present invention are highly effective and act against a wide variety of microorganisms.
It appears that the antimicrobial compositions of the present invention function by providing a surface that is substantially resistant to microbial adherence and attachment. In other words, the composition of the present invention can substantially prevent the occurrence of stage (i) of the biofilm formation process. This means that the microorganisms are unable to proliferate and form biofilms.
The antimicrobial composition provides a surface that prevents the adhesion and attachment of microorganisms due to the interaction of two low and high surface tension compounds, which has an effect of opposing surface tension.
Preventing biofilm formation and significantly reducing and diminishing the colonization of microorganisms substantially reduces the risk of infection or contamination. This is a benefit of the disinfecting product comprising the antimicrobial composition.
The antimicrobial compositions of the present invention are also generally capable of breaking down an established biofilm. The composition of the present invention seems to achieve the above object by dispersing the biofilm and effectively spreading it on the cell wall to cause its decomposition. The composition may also cause thinning and deformation of the biofilm, which makes the biofilm more susceptible to the antimicrobial agent, thus enhancing the efficacy of the antimicrobial agent in the composition.
Since the antimicrobial composition of the present invention actually disrupts the adhesion and adherence of microorganisms to surfaces, which is a common feature of many microorganisms including bacteria, fungi and molds, the composition is effective against a broad spectrum of microorganisms. Thus, the antimicrobial composition of the present invention has the advantage of preventing a wide variety of microorganisms from adhering and attaching to a surface, thereby preventing the formation of a biofilm thereon. It is also possible to sufficiently prevent the formation of a large number of colonies. Thus, the ability of the colonies to grow is significantly reduced or even inhibited. Thus, the antimicrobial compositions of the present invention provide overall control of microorganisms.
In addition to preventing colony growth, the antimicrobial compositions of the present invention appear to increase the relative longevity of colonies by preventing the production of new microorganisms. Thus, the antimicrobial agent of the present invention is contacted with "older" microorganisms, which are more sensitive to the antimicrobial agent than newer microorganisms. Thus, the antimicrobial agent is more effective at concentrations below its usual concentration. Thus, the compositions of the present invention enhance the effectiveness of the antimicrobial action of the antimicrobial agent as compared to use alone.
The antimicrobial composition of the present invention can be easily added to other materials such as functional materials. When added to the above materials, these materials become antimicrobial in nature and can modify the surface of the article (formulation) to substantially prevent microorganisms from adhering or attaching thereto.
Another advantage of the antimicrobial composition is that it does not require the inclusion of material compositions that are highly toxic to mammals. The antimicrobial agents used in the antimicrobial compositions are those that are generally known and commonly understood and tested. The efficacy of antimicrobial agents is known to be enhanced in the compositions of the present invention. Thus, antimicrobial agents with low toxicity can be used in antimicrobial compositions. In contrast, new antimicrobial agents for use in known sanitization techniques use "stronger", more toxic and/or less experimented materials.
The antimicrobial compositions of the present invention also do not contain materials or products containing heavy metals and their salts that produce long lasting residues or leachables. Thereby significantly reducing the risk of long-term damage by the antimicrobial composition.
The compositions of the invention do not interfere with the biochemical replication pathways controlled by microorganisms. Thus, there is less risk of development of resistant and resistant strains.
The surface tension of the first compound is greater than the surface tension of the second compound and is preferably lower than the surface tension of water at any given temperature. Thus, the first compound generally acts to reduce the surface tension of the water. The surface tension of the first compound is 20-35mN/m at 20 ℃.
The surface tension of the second compound is 8-14mN/m, preferably 10mN/m, at 20 ℃. The low surface tension of the second compound reduces non-specific binding to other components of the composition, particularly to aqueous or hydrated materials.
The first compound is preferably hydrophobic. The second compound is preferably hydrophilic. This provides a composition which is generally stable in both hydrophobic and hydrophilic materials. In addition, the hydrophobic first compound will typically attract the hydrophilic second compound in order to provide the desired reverse surface tension effect. This combination of properties is believed to produce a micro-interference effect that can disrupt biofilm formation. The fact that the effect is microscopic means that it has a strong effect on microorganisms, but no effect on larger macroorganisms.
While it is preferred that the first compound be hydrophobic and the second compound be hydrophilic, the first compound can be hydrophilic and the second compound can be hydrophobic.
Preferably, the first compound is a second antimicrobial agent. Thus, in addition to contributing to the surface effect, the first compound also acts as an antimicrobial agent. However, the inclusion of other ingredients in the composition can increase the effectiveness of the second antimicrobial agent.
The term "antimicrobial agent" refers to all chemical substances that are capable of destroying microorganisms.
The inclusion of first and second antimicrobial agents (hereinafter generically referred to as antimicrobial agents) in the compositions is well known and has been studied by the regulatory authorities. Antimicrobial agents generally have some effect when used alone. However, the efficacy of the antimicrobial agent is enhanced when used in combination with other ingredients in the compositions of the present invention.
Preferably the compositions of the present invention contain two or more antimicrobial agents. A typical composition may contain four antimicrobial agents.
The antimicrobial agent is preferably polar. This enables it to bind with other components of the composition, for example by hydrogen bonding or non-chemical bonding. This binding allows the antimicrobial agent to bind directly to the microorganism, while the other components of the composition of the invention bind themselves to the microbial cell wall. In this way, the antimicrobial is effective at low concentrations. The antimicrobial agent is not considered to form a chemical bond with the first and second compounds.
Preferably the composition comprises at least one first antimicrobial agent selected from bactericides, fungicides, algicides, bactericides and moldicides. More preferably the composition comprises a bactericide, a fungicide and a mildewcide.
The first antimicrobial agent is preferably an amphoteric compound, an iodine-carrying compound (iodophor), a phenolic compound, a quaternary ammonium compound, a hypochlorite, or a nitrogen-based heterocyclic compound.
The second antimicrobial agent is preferably a surfactant, more preferably a quaternary ammonium compound. Both the first and second antimicrobial agents may contain a quaternary ammonium compound.
Preferably, the antimicrobial compositions of the present invention contain one or more of quaternary ammonium compounds, phenolic compounds, and nitrogen-based heterocyclic compounds as antimicrobial agents.
Quaternary amines suitable for use in the present inventionThe compounds include the general formula R1R2R3R4N+X-Compounds in which one or two R radicals are alkyl, optionally substituted by aryl or interrupted by aryl or hetero atoms, e.g. oxygen, the other R radicals being identical or different C1-C4An alkyl group.
Preferred quaternary ammonium compounds include halobenzalkonium, aromatic ring-substituted halobenzalkonium such as ethyl-substituted halobenzalkonium, and double-chain quaternary ammonium compounds such as dialkyldimethylammonium compounds wherein the two non-methyl alkyl groups are selected from medium and long chain alkyl groups such as C8-C12Alkyl groups, preferably octyl and dodecyl.
Wherein R is a group (i.e. R)1、R2、R3、R4) Suitable quaternary ammonium compounds containing heteroatoms include domiphen bromide, benzalkonium chloride and methylbenzylammonium chloride.
Other quaternary ammonium compounds suitable for use in the antimicrobial composition include alkylpyridinium compounds such as cetylpyridinium chloride, and bridged cyclic amino compounds such as hexaammonium compounds.
Particularly preferred quaternary ammonium compounds include N-dodecyl-N, N-dimethylbenzylbenzalkonium chloride, N-dodecyl-N, N-dimethyl-N-tetradecylbenzbenzalkonium chloride and benzyl-C12-C16-alkyldimethyl-ammonium chloride.
Amphoteric compounds suitable for use in the present invention include long chain N-alkyl derivatives of amino acids. Long chain N-alkyl derivatives of glycine, alanine and beta-aminobutyric acid are preferred. Particularly preferred compounds include dodecyl beta-alanine, dodecyl beta-aminobutyric acid, dodecylamino-di (aminoethylamino) glycine and N- (3-dodecylamino) propylglycine.
The term "iodine-carrying compound" means a complex of iodine or triiodine and a carrier such as a neutral polymer. The carrier generally increases the solubility of iodine in the aqueous species, provides a sustained release of iodine and reduces the equilibrium concentration of free iodine.
Suitable polymeric carriers for preparing the iodine-carrying compounds include polyvinylpyrrolidone, polyether glycols such as polyethylene glycol, polyvinyl alcohol, polyacrylates, polyamides, polyalkylenes and polysaccharides.
Suitable phenolic compounds include methyl, ethyl, butyl, halogen and aryl substituted phenols. Preferred phenolic compounds include 2-phenylphenol, 2-benzyl-4-chlorophenol, 2-cyclopentanol-4-chlorophenol, 4-tert-amylphenol, 2-tert-butylphenol, 4-chloro-2-pentylphenol, 6-chloro-2-pentylphenol, p-chloro-m-xylenol, 2, 4, 4-trichloro-2-hydroxydiphenol, thymol, 2-isopropyl-3-methylphenol, chlorothymol, 3-methyl-4-chlorophenol, 2, 6-dichloro-4-n-alkylphenol, 2, 4-dichloro-m-xylenol, 2, 4, 6-trichlorophenol and 2-benzyl-4-chlorophenol.
Suitable hypochlorites include alkali and alkaline earth metal hypochlorites such as lithium, sodium, potassium and calcium hypochlorite. Other suitable hypochlorites include trisodium chlorophosphate and its various hydrates. Other suitable chlorine-containing or chlorine-releasing agents include chlorine dioxide and its precursors, as well as N, N-dichloro-4-carboxybenzenesulfonamide (haloamine), 1, 3-dichloro-5, 5-dimethylhydantoin (halane), and various chloroisocyanuric acid derivatives.
Suitable azaheterocyclic compounds include pyridine derivatives such as 4-pyridinecarboxylic acid hydrazide, 2-pyridinethiol-1-sodium oxide and bis (2-pyridylthio) zinc-1-dioxide, triazoles, thiazoles and imidazoles.
Particularly preferred antimicrobial compositions contain N-dodecyl-N, N-dimethylanilinium chloride, N-dodecyl-N, N-dimethyl-N-tetradecylanilinium chloride and benzyl-C12-C16-alkyldimethyl-ammonium chloride, 2-phenylphenol, 2-octyl-2H-isothiazolone, 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one.
The antimicrobial agent specifically selected for use in the composition will vary depending on the environment in which the composition is intended to be used.
The second compound is preferably chemically inert and has a structure capable of attaching to virtually any substrate. The second compound can remain on the surface for a long period of time. This means that the composition of the invention can be easily recharged.
The second compound can also bind to other ingredients in the compositions of the present invention through non-chemical bonds and is generally capable of adhering to and attracting a wide variety of polar materials, including various antimicrobial agents.
The second compound is preferably a surfactant or oil, more preferably a short chain surfactant or oil. The term "short chain" means C12-C20. Suitable second compounds include silanes, polyethylene glycols, sodium lauryl sulfate, soy lecithin, preferably siloxanes such as polysiloxanes or silicones.
The preferred second compound is polydimethylsiloxane, and the particularly preferred second compound is polydimethylsiloxane. For example, polydimethyl hydroxy siloxanes with viscosities of 100 and 400 centistokes may be included in the compositions of the present invention.
Preferably the composition contains 1-4% by volume of the second compound; however other ratios are possible and within the scope of the invention.
Suitable polar solvents for use in the composition include water, alcohols, esters, hydroxy esters and glycol esters, polyols and ketones. It appears that the polar solvent helps to provide a composition that is stable and does not separate into components.
Preferred alcohols for use in the composition include straight or branched chain C1-C5Alcohols, in particular methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, isobutanol, 2-methyl-1-butanol, 1-pentanol and pentanol (isomer mixtures).
Preferred esters for use in the composition include methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate, pentyl acetate (mixture of isomers), methyl pentyl acetate, 2-ethylhexyl acetate and isobutyl isobutyrate.
Preferred hydroxyl and glycol esters for use in the composition include ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, ethyl lactate, n-butyl lactate, 3-methoxy-n-butyl acetate, ethylene glycol diacetate, polysolvan O, 2, 4-trimethyl-3-hydroxypentyl 2-methylpropionate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, 3-methoxybutanol, butyl glycol, isobutyl glycol, methyl diethylene glycol, ethyl diethylene glycol, butyl diethylene glycol, isobutyl diethylene glycol, dipropylene glycol, ethylene glycol monohexyl ether, and diethylene glycol monohexyl ether.
Preferred polyhydric alcohols for use in the composition include ethylene glycol, propylene glycol, 1, 3-butanediol, 1, 4-butanediol, hexylene glycol, diethylene glycol, triethylene glycol and dipropylene glycol.
Preferred ketones for use in the composition include isobutyl heptyl ketone, cyclohexanone, methylcyclohexanone, methyl isobutenyl ketone, pentoxone, acetylacetone, diacetone alcohol, isophorone, methyl butyl ketone, ethyl propyl ketone, methyl isobutyl ketone, methyl amyl ketone, methyl isoamyl ketone, ethyl butyl ketone, ethyl amyl ketone, methyl hexyl ketone, diisopropyl ketone, diisobutyl ketone, acetone, methyl ethyl ketone, methyl propyl ketone, and diethyl ketone.
Particularly preferred polar solvents for use in the composition include isopropanol, diethylene glycol and dipropylene glycol.
Preferably the composition contains 1 to 70 volume% polar solvent, but since the main purpose of the solvent is dilution, it is contemplated that virtually any proportion of polar solvent is possible within the scope of the invention.
A particularly preferred antimicrobial composition contains 32 volume percent of N-dodecyl-N, N-dimethylanilinium chloride and N-dodecyl-N,mixture of N-dimethyl-N-tetradecylbenzenemethanaminium chloride (2.33: 1), 6.0% by volume of benzyl-C12-C16-a mixture of alkyldimethyl-ammonium chloride and 2-phenylphenol (2: 1), 6.0% by volume of 2-octyl-2H-isothiazol-3-one, 16.0% by volume of a mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one (3: 1), 1.0% by volume of the polysiloxane mixture and the remaining volume of isopropanol.
Another particularly preferred antimicrobial composition comprises a mixture of 32 volume percent N-dodecyl-N, N-dimethylanilinium chloride and N-dodecyl-N, N-dimethyl-N-tetradecylanilinium chloride (2.33: 1), 6.0 volume percent benzyl-C12-C16A mixture of alkyldimethyl-ammonium chloride and 2-phenylphenol (2: 1), 6.0% by volume of 2-octyl-2H-isothiazol-3-one, 16.0% by volume of a mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one (3: 1), 1.0% by volume of polydimethylsiloxane and the remaining volume of isopropanol.
Another particularly preferred antimicrobial composition contains a mixture of 5.0% by volume of N-dodecyl-N, N-dimethylanilinium chloride and N-dodecyl-N, N-dimethyl-N-tetradecylanilinium chloride (2.33: 1), 5.0% by volume of benzyl-C12-C16-a mixture of alkyldimethyl-ammonium chloride and 2-phenylphenol (2: 1), 12.0% by volume of 2-octyl-2H-isothiazol-3-one, 32.0% by volume of a mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one (3: 1), 1.0% by volume of the polysiloxane mixture and the remaining volume of diethylene glycol.
Another particularly preferred antimicrobial composition contains a mixture of 6.0% by volume of N-dodecyl-N, N-dimethylanilinium chloride and N-dodecyl-N, N-dimethyl-N-tetradecylanilinium chloride (2.33: 1), 6.0% by volume of benzyl-C12-C16A mixture of alkyldimethyl-ammonium chloride and 2-phenylphenol (2: 1), 16.0% by volume of 2-octyl-2H-isothiazol-3-one, 32.0% by volume of 5-chloro-2-methyl-2H-isothiazol-3-one-a mixture of 3-ketone and 2-methyl-2H-isothiazol-3-one (3: 1), 1.0% by volume of the polysiloxane mixture and the remaining volume of isopropanol.
Another particularly preferred antimicrobial composition contains a mixture of 6.0% by volume of N-dodecyl-N, N-dimethylanilinium chloride and N-dodecyl-N, N-dimethyl-N-tetradecylanilinium chloride (2.33: 1), 6.0% by volume of benzyl-C12-C16-a mixture of alkyldimethyl-ammonium chloride and 2-phenylphenol (2: 1), 16.0% by volume of 2-octyl-2H-isothiazol-3-one, 32.0% by volume of a mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one (3: 1), 1.0% by volume of a polysiloxane mixture and the remaining volume of dipropylene glycol.
According to another aspect of the invention there is provided a formulation comprising an antimicrobial composition and at least one other functional material.
Suitable functional materials include plastics, fibres, coatings, films, laminates, adhesives, sealants, clays, china clay, concrete, sand, paints, varnishes, lacquers, cleaners or settable or curable compositions such as fillers, grouts, mastics and putties.
The plastic may be in the form of films, sheets, stabs and molded plastic parts. Suitable plastic materials can be prepared from the following materials: polyesters such as polyethylene terephthalate, polybutylene terephthalate, polyamides such as nylon, polyimides, polypropylene, polyethylene, polybutylene, polymethylpentene, polysiloxanes, polyvinyl alcohol, polyvinyl acetate, ethylene-vinyl acetate copolymers, polyvinyl chloride, poly-1, 2-dichloroethylene, epoxy resins, phenol and polycarbonate cellulosics, cellulose acetate, polystyrene, polyurethanes, acrylics, polymethylmethacrylate, acrylonitrile, butadiene-styrene copolymer, acrylonitrile-styrene-acrylic copolymer, acetals, polyketones, polyphenylene ether, polyphenylene sulfide, polyphenylene ether, polysulfone, liquid crystal polymers and fluoropolymers, amino resins, thermoplastic elastomers, rubbers such as styrene butadiene rubber and nitrile butadiene rubber, polyacetal (polyoxymethylene), and mixtures and copolymers thereof.
Formulations containing the antimicrobial composition and a plastic material as a functional material are useful, for example, in forming products such as automotive parts, shower curtains, mats, protective covers, sound tapes, packaging, gaskets, waste containers, multi-purpose containers, brush holders, sponges, mops, vacuum bags, insulators, plastic films, insulation for indoor and outdoor furniture, pipes, wires and cables, plumbing and accessories, house siding, gaskets, nonwoven fabrics, kitchen and bathroom hardware, instruments and equipment, countertops, sinks, floors, floor coverings, tiles, trays, conveyor belts, footwear including boots, sports equipment, and tools.
Suitable fabrics may be prepared from acetates, polyesters such as PET and PTT, polyolefins, polyethylene, polypropylene, polyamides such as nylon, acrylon, viscose, polyurethane, and rayon, polyvinyl alcohol, polyvinyl chloride, polyvinylidene chloride, polysaccharides, and copolymers and blends thereof.
Formulations containing the antimicrobial composition and fibers as functional materials are useful, for example, in a variety of applications such as mattress cover liners and fillings, pillow cases, sheets, blankets, fibrous waddings for comforters and pillows, curtains, drapes, carpets and carpet liners, rugs, upholstery, tablecloths, napkins, wipes, mops, towels, bags, wallcoverings, cushioning, sleeping bags, and bristles. The fibers are also suitable for use in automotive and truck upholstery, blankets, rear platforms, trunk links, convertible tops, and liners. In addition, the fibers are also suitable for use in umbrellas, outerwear, uniforms, coats, aprons, sportswear, pajamas, stockings, socks, and jackets and linings, shoes, gloves and helmets, garments and upholstery, and bristles, artificial leather, filter paper, book covers, mops, canvas, ropes, tents and other outdoor equipment, tarpaulins and awnings.
Suitable coatings for use in the formulation include water-based, solvent-based, 100% solids, and/or radiation-curable coatings. The coating may be a liquid or powder coating.
Suitable coatings, films and laminates include alkyd resins, amino resins such as melamine formaldehyde and urea formaldehyde, polyesters such as unsaturated polyesters, PET, PBT, polyamides such as nylon, polyimide, polypropylene, polyvinyl acetate, ethylene vinyl acetate, polyvinyl chloride, polyvinylidene chloride, epoxy resins, phenol and polycarbonate cellulosics, cellulose acetate, polystyrene, polyurethane, acrylic resins, polymethyl methacrylate, acrylonitrile-butadiene-styrene copolymers, acrylonitrile-styrene-acrylic copolymers, acetals, polyketones, polyphenylene ethers, polyphenylene sulfides, polyphenylene ethers, polysulfones, liquid crystal and fluoropolymer polymers, thermoplastic elastomers, rubbers such as styrene-butadiene and nitrile-butadiene rubbers, polyacetal (polyoxymethylene) and mixtures and copolymers thereof.
Formulations containing the antimicrobial composition and a coating as a functional material can be used, for example, for glazing walls, building board, floors, concrete, siding, roofing shingles, industrial equipment, natural and synthetic fibers and fabrics, furniture, automotive and vehicular parts, packaging, paper products (wallpaper, paper towels, book covers), insulating fabrics and cement tiles, and glazing glazes for plumbing fixtures such as toilets, sinks, and countertops.
Suitable adhesives and sealants for use in the formulations include hot melt, aqueous solvent based 100% solids and radiation curable adhesives and sealants.
Suitable binders and sealants include alkyd resins, amino resins such as melamine formaldehyde and urea formaldehyde, polyesters such as unsaturated polyesters, PET, PBT, polyamides such as nylon, polyimides, polypropylene, polyethylene, polybutylene, polymethylpentene, polysiloxanes, polyvinyl alcohol, polyvinyl acetate, ethylene-vinyl acetate copolymers, polyvinyl chloride such as plastisols, polyvinylidene chloride, epoxy resins, phenol and polycarbonate, cellulosics, cellulose acetate, polystyrene, polyurethanes, acrylic resins, polymethyl methacrylate, acrylonitrile-butadiene-styrene copolymers, acrylonitrile-styrene-acrylic copolymers, acetals, polyketones, polyphenylene ethers, polyphenylene sulfides, polyphenylene ethers, polysulfones, liquid crystal and fluoropolymer, thermoplastics, rubbers (including styrene-butadiene rubber, styrene-butadiene-styrene copolymer, polyethylene-styrene-acrylic copolymer, polyethylene-styrene-butadiene-styrene-acrylic copolymer, nitrile rubber, CR), polyacetal (polyoxymethylene) and mixtures and copolymers thereof.
Formulations containing the antimicrobial composition and an adhesive or sealant as a functional material are useful, for example, in the manufacture of wood and plastic composites, adhesives for tile, wood, paper, cardboard, rubber and plastic, window glazing, grout, pipe sealants, electrical appliances, bathrooms, shower stations, adhesives for prescriptions and buildings, sealants and insulation.
Formulations containing the antimicrobial composition and clay, porcelain, china clay, concrete, sand or grout as functional material can be used in, for example, toilets, sinks, tiles, floors, plasters, cat litter (cat litters), drains and sewer pipes.
The antimicrobial compositions can be used in combination with a variety of functional compounds in the manufacturing, contractor, and construction industries. The nature of the antimicrobial composition may vary depending on the particular functional compound and the number and characteristics of the particular functional compound or microorganism present in its environment of use.
The formulation preferably contains 0.1 to 5.0 wt%, more preferably 0.1 to 4.0 wt%, still more preferably 0.5 to 2.0 wt% of the antimicrobial composition.
The antimicrobial composition is effective against a broad spectrum of microorganisms even when combined with another functional material to provide the formulation of the present invention. The formulation may optionally be applied to a surface. The formulations provide long-term antimicrobial action on the treated surface or surfaces to which the material is bound, both under dry and wet conditions. This enables disinfection of the surface so that the surface and product can be protected from rapid microbial replication, thereby significantly reducing the risk of contamination and infection.
The antimicrobial composition can flow through most of the functional materials it is incorporated in the formulations of the present invention. This is due to the presence of surfactant materials and oils and short chain molecules. To maintain such fluidity, the surfactant material and the oil preferably have a carbon chain length of not more than 20.
The antimicrobial composition tends to move across the concentration gradient and onto the surface of the product into which the composition has been incorporated. This is similar to the behaviour of plasticizers in polymers.
The antimicrobial compositions and formulations typically begin to separate into their constituent parts when they are in continuous contact with water for more than 6-8 hours. Once the compositions and formulations are separated into their component parts, the antimicrobial effect of the antimicrobial compositions and formulations is significantly reduced. The components become carbon sources and nutrients for a variety of microorganisms. Thus, the antimicrobial compositions and formulations are capable of degrading when immersed in water, resulting in a low toxicity leacheate/leach solution that has a short residence time in the environment.
The low toxicity of the leacheate is believed to be due to the combination of the antimicrobial agent with the second compound such that the composition is not readily separable in the presence of water.
The formulation can be designed to be stable and effective in most production environments. The formulations are generally stable at temperatures up to 200 ℃.
The fluidity of the product allows materials that are frequently washed or rinsed to "replenish" the antimicrobial composition during regular cleaning or maintenance.
Typically during the wash process, the antimicrobial composition is mixed into a simple conventional detergent solution or added to the "final rinse water". Due to the presence of its hydrophobic components, the antimicrobial composition is drawn to the surface of the product to be "replenished". Thus, the disinfecting properties of the formulation can be restored without the need for remanufacturing or difficult handling procedures.
Any rinse or leachant containing the antimicrobial composition or formulation diluted with the above-described make-up solution and water will rapidly separate into biodegradable components as described above.
According to another aspect of the present invention there is provided the use of an antimicrobial composition to prevent the formation of microbial colonies on a surface on which the composition is used.
According to another aspect of the invention there is provided the use of a formulation to prevent the formation of microbial colonies on a surface on which the formulation is used.
Antimicrobial compositions and formulations have antibacterial effects against a variety of gram-positive and gram-negative bacteria.
For example, effective against the following bacteria:
bacillus, e.g. Bacillus subtilis, Bacillus cereus
Genus Brevibacterium
Brucella, e.g. Brucella abortus
Lactobacillus genus
Proteus vulgaris
Pseudomonas aeruginosa
Salmonella
Staphylococcus, such as methicillin-resistant Staphylococcus aureus (MRSA)
Genus Streptococcus
Flavobacterium genus
Genus Escherichia
Aeromonas genus
Antimicrobial compositions and formulations are also effective against fungi and yeasts such as:
penicillium genus
Aspergillus niger
Cladosporium genus
Fusarium genus
Paecilomyces
Streptomyces genus
Saccharomyces, e.g. Saccharomyces cerevisiae
Candida albicans
Antimicrobial compositions and formulations are also effective against certain algae, such as:
chlorella pyrenoidosa (berk.) Sacc
Synechococcus
Necklace algae
According to another aspect of the present invention there is provided a process for the preparation of an antimicrobial composition, the process comprising the steps of: (i) mixing together a first compound and a first antimicrobial agent, (ii) adding a second compound to the mixture of the first compound and the first antimicrobial agent, (iii) adding a polar solvent to the mixture of the first and second compounds and the first antimicrobial agent, and (iv) stirring the resulting mixture until a clear solution is formed.
According to another aspect of the present invention there is provided a method of preparing a formulation comprising the step of adding an antimicrobial composition to a functional compound.
1. The present invention provides an antimicrobial composition comprising (i) a first compound having a high surface tension of from 20 to 35mN/m, (ii) a second compound having a low surface tension of from 8 to 14mN/m and selected from silanes, soy lecithin, polysiloxanes and mixtures thereof, (iii) a first antimicrobial agent and (iv) a polar solvent, the composition being primarily for preventing the formation of microbial colonies on a surface.
2. The antimicrobial composition according to item 1, wherein the surface tension of the second compound is 10 mN/m.
3. The antimicrobial composition according to item 1 or 2, wherein the first compound is hydrophobic.
4. The antimicrobial composition of claim 1, wherein the second compound is hydrophilic.
5. The antimicrobial composition of claim 1 wherein the first compound is a second antimicrobial agent.
6. The antimicrobial composition of claim 5, wherein the first and/or second antimicrobial agent is polar.
7. The antimicrobial composition according to item 1, comprising at least one antimicrobial agent selected from the group consisting of bactericides, fungicides, algicides, bactericides and moldicides.
8. The antimicrobial agent according to item 7, comprising at least one antimicrobial agent selected from the group consisting of bactericides, fungicides and mildewcides.
9. The antimicrobial composition of claim 5 wherein the second antimicrobial agent is a quaternary ammonium compound.
10. The antimicrobial composition according to item 1, comprising at least one first antimicrobial agent selected from the group consisting of an amphoteric compound, an iodine-carrying compound, a phenolic compound, a quaternary ammonium compound, a hypochlorite, and a nitrogen-based heterocyclic compound.
11. An antimicrobial composition according to claim 9, wherein the quaternary ammonium compound has the general formula R1R2R3R4N+X-Wherein one or two R groups are alkyl, optionally substituted by aryl or interrupted by aryl or a heteroatom, the other R groups being identical or different C1-C4An alkyl group.
12. The antimicrobial composition of claim 11 wherein the quaternary ammonium compound is selected from the group consisting of halobenzalkonium, aromatic ring substituted halobenzalkonium, and dialkyldimethylammonium compounds wherein the two non-methyl alkyl groups are selected from C8-C12An alkyl group.
13. The antimicrobial composition of claim 12 wherein the quaternary ammonium compound is selected from the group consisting of N-dodecanealkyl-N, N-dimethyl benzalkonium chloride, N-dodecyl-N, N-dimethyl-N-tetradecyl benzalkonium chloride and benzyl-C12-C16-alkyldimethyl-ammonium chloride.
14. An antimicrobial composition according to claim 10, wherein the amphoteric compound is a long chain N-alkyl derivative of an amino acid.
15. An antimicrobial composition according to claim 14, wherein the amphoteric compound is selected from the group consisting of long chain N-alkyl derivatives of glycine, alanine and β -aminobutyric acid.
16. The antimicrobial composition of claim 15, wherein the amphoteric compound is selected from the group consisting of dodecyl beta-alanine, dodecyl beta-aminobutyric acid, dodecylamino-bis (aminoethylamino) glycine, and N- (3-dodecylamino) propylglycine.
17. An antimicrobial composition according to claim 10 wherein the iodine bearing compound is selected from the group consisting of iodine or triiodine complexes with polyvinyl pyrrolidone, polyether glycols, polyvinyl alcohol, polyacrylates, polyamides, polyalkylene and polysaccharides.
18. The antimicrobial composition according to item 10, wherein the phenolic compound is selected from the group consisting of methyl, ethyl, butyl, halogen and aryl substituted phenols.
19. The antimicrobial composition according to item 10, wherein the phenolic compound is selected from the group consisting of 2-phenylphenol, 2-benzyl-4-chlorophenol, 2-cyclopentanol-4-chlorophenol, 4-tert-amylphenol, 4-tert-butylphenol, 4-chloro-2-pentylphenol, 6-chloro-2-pentylphenol, p-chloro-m-xylenol, 2, 4, 4-trichloro-2-hydroxydiphenol, thymol, 2-isopropyl-3-methylphenol, chlorothymol, 3-methyl-4-chlorophenol, 2, 6-dichloro-4-n-alkylphenol, 2, 4-dichloro-m-xylenol, 2, 4, 6-trichlorophenol and 2-benzyl-4-chlorophenol.
20. The antimicrobial composition of item 10 wherein the hypochlorite is selected from the group consisting of alkali metal and alkaline earth metal hypochlorites.
21. The antimicrobial composition of item 20 wherein the hypochlorite is selected from the group consisting of lithium, sodium, potassium and calcium hypochlorites.
22. The antimicrobial composition according to item 1, comprising trisodium chlorophosphate and hydrates thereof.
23. The antimicrobial composition according to item 1, comprising chlorine dioxide or a precursor thereof, N-dichloro-4-carboxybenzenesulfonamide, 1, 3-dichloro-5, 5-dimethylhydantoin or a derivative of chloroisocyanuric acid.
24. The antimicrobial composition according to item 10, wherein the nitrogen-based heterocyclic compound is selected from the group consisting of pyridine derivatives, triazoles, thiazoles, and imidazoles.
25. The antimicrobial composition according to claim 24, wherein the nitrogen-based heterocyclic compound is selected from the group consisting of 4-pyridinecarboxylic acid hydrazide, sodium 2-pyridinethiol, and bis (2-pyridinethio) zinc-1-dioxide.
26. The composition of claim 1 wherein the antimicrobial agent is selected from the group consisting of N-dodecyl-N, N-dimethyl benzalkonium chloride, N-dodecyl-N, N-dimethyl-N-tetradecyl benzalkonium chloride, and benzyl-C12-C16Alkyl dimethyl-ammonium chloride, 2-phenylphenol, 2-octyl-2H-isothiazol-3-one, 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one.
27. The antimicrobial composition according to item 1, wherein the second compound is a polysiloxane or a blend of polysiloxanes.
28. The antimicrobial composition of claim 27 wherein the second compound is a polydimethyl hydroxy siloxane.
29. The antimicrobial composition of item 1, comprising 1-4% by volume of the second compound.
30. The antimicrobial composition according to item 1, wherein the polar solvent is selected from the group consisting of water, alcohols, esters, hydroxyl or glycol esters, polyols and ketones.
31. The antimicrobial composition of item 30 wherein the polar solvent is selected from the group consisting of isopropyl alcohol, diethylene glycol, and dipropylene glycol.
32. The antimicrobial composition according to item 1, comprising 1 to 70 vol.% of a polar solvent.
33. The antimicrobial composition according to item 1, wherein the composition comprises a mixture of 32% by volume of N-dodecyl-N, N-dimethylanilinium chloride and N-dodecyl-N, N-dimethyl-N-tetradecylanilinium chloride (2.33: 1), 6.0% by volume of benzyl-C12-C16A mixture of alkyldimethyl-ammonium chloride and 2-phenylphenol (2: 1), 6.0% by volume of 2-octyl-2H-isothiazol-3-one, 16.0% by volume of a mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one (3: 1), 1.0% by volume of a polysiloxane mixture and 39% by volume of isopropanol.
34. The antimicrobial composition according to item 1, wherein the composition comprises a mixture of 32% by volume of N-dodecyl-N, N-dimethylanilinium chloride and N-dodecyl-N, N-dimethyl-N-tetradecylanilinium chloride (2.33: 1), 6.0% by volume of benzyl-C12-C16A mixture of alkyldimethyl-ammonium chloride and 2-phenylphenol (2: 1), 6.0% by volume of 2-octyl-2H-isothiazol-3-one, 16.0% by volume of a mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one (3: 1), 1.0% by volume of polydimethylsiloxane and 39% by volume of isopropanol.
35. A formulation comprising an antimicrobial composition as described in any of the above and a functional material.
36. The formulation of claim 35, wherein the functional material is selected from the group consisting of plastics, fibers, coatings, films, laminates, adhesives, sealants, clays, china clay, concrete, sand, paints, varnishes, lacquers, cleaning agents and fixable or curable compositions.
37. The formulation of item 36, the fixable or curable composition is selected from the group consisting of fillers, cement slurries, cements, and putties.
38. The formulation according to any one of claims 35 to 37 to 36, wherein the formulation contains from 0.1 to 5.0% by weight of the antimicrobial composition.
39. The formulation of item 38, wherein the formulation contains 0.5-2.0% by weight of the antimicrobial composition.
40. Use of an antimicrobial composition according to any one of claims 1 to 34 to prevent the formation of microbial colonies on a surface on which the antimicrobial composition is used.
41. Use of a formulation according to any one of claims 35 to 39 to prevent the formation of microbial colonies on a surface on which the formulation is used.
42. A method of preparing an antimicrobial composition according to any one of claims 1 to 34, comprising the steps of: (i) mixing together a first compound and a first antimicrobial agent, (ii) adding a second compound to the mixture of the first compound and the first antimicrobial agent, (iii) adding a polar solvent to the mixture of the first and second compounds and the first antimicrobial agent and (iv) stirring the resulting mixture until a clear solution is formed.
43. A method of making a formulation according to any one of claims 35 to 39, comprising the step of adding an antimicrobial composition to the functional compound.
The invention is illustrated with reference to the following examples, but is not limited thereto.
EXAMPLE 1 preparation of antimicrobial composition ("D4L")
Preparing a composition of the invention containing the indicated amounts of ingredients (a) to (f):
(a) 32.0% by volume of a mixture of two benzalkonium chlorides (2.33: 1), namely N-dodecyl-N, N-dimethylbenzalkonium chloride and N-dodecyl-N, N-dimethyl-N-tetradecylphenylmethylammonium chloride (trade name: BAC-50 m);
(b) 6.0% by volume of benzyl-C12-C16A 2: 1 mixture of alkyldimethyl-ammonium chloride (CAS number 68424-85-1) and 2-phenylphenol (trade name: Acticide 50X);
(c)6.0 vol% of 2-octyl-2H-isothiazol-3-one (trade name: A-DW);
(d) 16.0% by volume of a 3: 1 mixture of 5-chloro-2-methyl-2H-isothiazol-3-one and 2-methyl-2H-isothiazol-3-one (trade name: A-I4);
(e)1.0 vol% of polydimethylsiloxane (trade name: PD-D)
And
(f) 39% by volume of an isopropanol mixture (isopropanol, n-propanol and water, to the azeotropic limit about 1.0%).
Antimicrobial agents a, b, c and d were mixed together in the order described above at room temperature. The resulting mixture is then stirred well and polysiloxane (e) is added to the mixture. The resulting mixture was stirred and isopropanol (f) was added. The mixture was then stirred until a clear solution was obtained.
This clear solution is referred to herein as "D4L".
Example 2 preparation of antimicrobial compositions ("LCF")
Preparing a composition of the invention containing indicated amounts of ingredients (a) to (f):
(a) 32.0% by volume of a mixture of two benzalkonium chlorides (2.33: 1), namely N-dodecyl-N, N-dimethylbenzalkonium chloride and N-dodecyl-N, N-dimethyl-N-tetradecylphenylmethylammonium chloride (trade name: BAC-50 m);
(b) 6.0% by volume of benzyl-C12-C162: 1 blend of (E) -alkyldimethyl-ammonium chloride (CAS number 68424-85-1) and 2-phenylphenolSubstance (trade name: activide 50X);
(c) 6.0% by volume of 2-phenylphenol;
(d) 16.0% by volume of a 25% solution of 1, 2-benzisothiazolin-3-one in isopropanol;
(e)1.0 vol% of polydimethylsiloxane (trade name: PD-D)
And
(f) 39% by volume of an isopropanol mixture (isopropanol, n-propanol and water, to the azeotropic limit about 1.0%).
Antimicrobial agents a, b, c and d were mixed together in the order described above at room temperature. The resulting mixture was then stirred well, and polydimethylsiloxane (e) was added to the mixture. The resulting mixture was stirred and isopropanol (f) was added. The mixture was then stirred until a clear solution was obtained. This clear solution is referred to herein as "LCF".
Example 3A detergent was prepared containing the antimicrobial composition of example 1 (i.e., D4L)
Amphoteric nonionic detergents such as rinses at pH6-8 are diluted with water at a ratio of 1 part by volume detergent to 25 parts by volume water. To this solution was added 0.5-2.0% by volume of the antimicrobial composition prepared in example 1 (i.e., D4L).
Example 4 efficacy of antimicrobial formulations against E.coli, S.aureus and P.aeruginosa
Method of producing a composite material
Two samples were tested: a detergent formulation prepared according to example 3 containing 2% by volume of the antimicrobial composition of example 1, and a neutral detergent. Neutral detergents are used as standard references.
Bacterial cultures (0.1ml) in nutrient medium were plated on pre-sterilized petri dishes over a 7X 5cm area. The bacterial culture was then allowed to dry for 30 minutes.
The inoculated area is then wiped with a test wipe soaked in water or test solution to bring the test solution into contact with the bacteria. The test solutions were coated using a water-absorbent cloth or an inoculating loop. The untreated inoculated area was left as an "unclean control" in which the infected area was not washed or even wiped with water. The bacteria remaining on the surface of the petri dish were counted after 15 and 30 seconds.
The count of bacteria remaining on the surface of the petri dish was performed as follows: the sterile swab was wetted in sterile peptone solution (0.1%), the area pre-sampled was wiped thoroughly with the swab, and the swab was rotated while the appropriate area was wiped with the swab. Then the swab is put back into the sterile test tube; add ringer's solution (5ml, 1/4 concentration); the swab was allowed to stand for at least 10 minutes.
Swab tubes were plated in ten-fold serial dilutions using Miles and Misra TotalViable Count Technique and incubated overnight at 37 ℃. The number of Colony Forming Units (CFU) was then counted (considered as viable individuals).
Computing
The log reduction in the number of bacteria compared to the water control and the unclean control was calculated.
The total number of CFUs per ml of neat sample in each test sample and control was calculated.
The log of the number of CFUs for the water control or the uncleaned control was calculated to give the a value. Repeating this procedure for the tested antimicrobial compositions yields B values.
Log reduction (a log water or CFU of uncleaned control, B log CFU of test sample).
Log reductions greater than 4 were considered effective.
TABLE 1 results
| Composition comprising a metal oxide and a metal oxide | Biological organisms | Log reduction after 15 seconds | Log reduction after 30 seconds |
| Antimicrobial compositions | Escherichia colia | 1.0 | ＞＞4.0 |
| Antimicrobial compositions | Staphylococcus aureusb | ＞4.9 | ＞4.9 |
| Antimicrobial compositions | Pseudomonas aeruginosac | 1.8 | 3.3 |
a total viable count of 6.8 × 108
b total viable bacteria 5.8 × 108
c Total viable count 1.5X 108
Conclusion
When tested against E.coli, the log reduction of 2% volume antimicrobial composition solution was 1.0 after 15 seconds and > 4.0 after 30 seconds.
When tested against staphylococcus aureus, the log reduction of 2% volume antimicrobial composition solution was > 4.9 after 15 seconds.
When tested against pseudomonas aeruginosa, the log reduction of 2% by volume antimicrobial composition solution was 1.8 after 15 seconds and 3.3 after 30 seconds.
Example 5 resistance of paint film formulations containing antimicrobial compositions to Dry film fungi and algal colonies
The following formulations containing paint and antimicrobial composition of example 1 were tested:
| composition numbering | Volume% of antimicrobial composition |
| Control | 0.00％ |
| 1 | 0.50％ |
| 2 | 0.75％ |
| 3 | 1.00％ |
| 4 | 1.50％ |
| 5 | 2.00％ |
method-Dry film fungus resistance test (according to British Standard BS3900 Part G6)
Each formulation was coated on a 6X 9cm plasterboard. Each formulation was coated on gypsum board in two layers and dried between each layer for 24 hours. When the plate has dried, it is spray inoculated with a mixed spore suspension prepared from fungi (including yeasts) isolated from, or known to grow on, the painted surface. The test panels were hung in a 24 ℃ high humidity cabinet for 4 weeks, and the fungal growth results were visually and microscopically evaluated. Fungal growth ratings were rated according to BS3900 PartG 6.
The microorganisms used were:
aspergillus versicolor
Aureobasidium pullulans
Dendritic spores
Penicillium purpurogenum
Phoma violaceae
Rhodotorula rubra
Sporobolomyces rubra
Stachybotrys chartarum
Ulocladium atrum
Method-dry film algae resistance test-vermiculite bed method
Each preparation was applied to a 10X 10cm calcium silicate board. Each formulation was coated on gypsum board in two layers and dried between each layer for 24 hours. After the plates were dried, the plates were etched with a QUV Accelerated weather Tester using a water spray cycle for 125 hours. Each plate was then cut in half. The half-plate was placed in a sealed lid in a transparent plastic box and water (800 cm)3) Wetted vermiculite (200g) surface. Each plate was inoculated with the mixed algae suspension spray three times every two weeks and sprayed with water every week. The plates were incubated at 20 ℃ for 13 weeks and illuminated daily with 30W mesh-type fluorescent tubes (producing approximately 1000 lux) for 16 hours. The algae growth results were evaluated visually and microscopically.
The microorganisms used were:
Chlorella emersonii
Gloeocapsa alpicola
Nostoc commune
genus Synechococcus
Stichococcus bacillaris
Stigeoclonium tenue
Trentepohlia aurea
Trentepohlia odorata
Results
TABLE 2 Dry film fungal resistance test
| Composition comprising a metal oxide and a metal oxideNumbering | Antimicrobial agent% by volume | Grade observed*(4 weeks) |
| Control | 0.00％ | 4(40+) |
| 1 | 0.50％ | 3(30+) |
| 2 | 0.75％ | 2(10+) |
| 3 | 1.00％ | 2(5+) |
| 4 | 1.50％ | 2(5+) |
| 5 | 2.00％ | 0(0) |
*The average rating of the parallel assay plates is given.
TABLE 3 Dry film algae resistance test
| Composition numbering | Antimicrobial agent% by volume | Membrane algae growth-repeat 1 | Grade/intensity-repeat 2 |
| Control | 0.00％ | 4(50+) | 4(40+) |
| 1 | 0.50％ | 3(20+) | 3(20+) |
| 2 | 0.75％ | 2(10+) | 3(15+) |
| 3 | 1.00％ | 2(10+) | 2(10+) |
| 4 | 1.50％ | 2(10+) | 2(10+) |
| 5 | 2.00％ | 2(5+) | 2(5+) |
Growth grade
The first number represents the fungal growth coverage as follows:
0-no growth
1 ═ micro growth
2-1-10% growth coverage
Growth coverage of 11-30%
Growth coverage of 31-70 ═ 4%
Growth coverage of 71-100 ═ 5%
The second number in parentheses represents the following% coverage and evaluation of the strength rating:
0 ═ growth is almost difficult to see with the naked eye
Slight growth
Moderate growth ++ ═
Dense growth of +++,
conclusion
The control sample (without antimicrobial composition) was found to be sensitive to dry film fungus and algae colonization.
The addition of 1.0% antimicrobial composition was found to control the level of fungal and algal populations to meet the passing criteria, i.e., less than 20%.
Example 6 microbiological testing of MRSA on coil coating plates (coil coating plates) treated with the antimicrobial composition of example 1
Roll-coated panels manufactured by BeckerIndustrial Coatings ltd, of leipu were treated with a range of concentrations of the antimicrobial composition of example 1. Plates were then tested to demonstrate whether they were resistant to methicillin-resistant Staphylococcus aureus (MRSA).
The plates were coated as follows:
s1 roll-coated sheet, 1.0 vol.% antimicrobial composition
S2 roll-coated sheet, 1.5 vol.% antimicrobial composition
S3 roll-coated board, 2.0 vol.% antimicrobial composition
S4 roll-coated board, 2.5 vol.% antimicrobial composition
S5 roll-coated sheet, 3.0 vol.% antimicrobial composition
S6 roll-coated board, 0 vol% antimicrobial composition (control)
Method of producing a composite material
MRSA cultures were diluted to approximately 1.5X 10 with sterile deionized water4CFU/ml. 1ml of this solution was placed on a roller-coating plate and an area of approximately 5cm by 5cm was coated continuously with a hand-held applicator for a contact time of 1 minute. The cultures were immediately recovered from the plate with a swab and transferred to a general purpose bottle containing the neutralising agent (1ml) and maximum recovery diluent (9 ml). Preparing 10-fold serial diluent, and taking the diluentAliquots of 0.1ml were spread on nutrient agar and the experiment repeated. Plates were incubated at 37 ℃ for 24 hours and 48 hours, and read using conventional techniques.
This procedure was repeated with the culture but with a contact time of 5 minutes. All six samples were subjected to the same protocol.
TABLE 4 results
| Sample(s) | Contact time 1 minute (CFU/ml) | Contact time 5 minutes (CFU/ml) |
| S1 | 82 | 55 |
| S2 | 73 | 50 |
| S3 | 60 | 38 |
| S4 | 55 | 35 |
| S5 | 49 | 30 |
| S6 | 1.1×103 | 2.5×102 |
Conclusion
All test specimens (S1-S5) caused a significant reduction in the number of bacteria (from 1.5X 10) at 1 minute contact time3CFU/ml), the reduction was less after 5 minutes. Complete killing of the bacteria was not achieved with 5 minutes of contact.
The control sample (S6) caused a small reduction in the number of bacteria (from 1.5X 10) at 1 minute contact time3CFU/ml), which may be mainly due to the difficulty in recovering the culture from the plate using the wiping technique. After a contact time of 5 minutes, the bacterial count of the control sample decreased significantly, mainly due to the drying out of the culture during the continuous spreading on the plate.
Coil coatings treated with the antimicrobial compositions were effective to significantly reduce MRSA bacterial levels at all concentrations tested when contacted for short periods in aqueous media.
These coatings can be very effective in participating in controlling MRSA bacterial contamination in hospitals and similar environments.
Example 7 microbiological testing of MRSA on food safe PVC94 laminated HMG boards treated with the antimicrobial composition of example 1
A panel from h.marcel Guest Ltd (HMG) coated with a food safe PVC94 layer article was treated with a paint and 2 vol% of an antimicrobial composition prepared according to example 1 in order to demonstrate whether it is resistant to Methicillin Resistant Staphylococcus Aureus (MRSA).
Sample(s)
S1 PVC94 laminate, 2 vol% antimicrobial composition, transparent.
S2 control, clear.
S3 PVC94 laminate, 2 vol% antimicrobial composition, white.
S4 control, white.
Method of producing a composite material
MRSA cultures were diluted to approximately 1.5X 10 with sterile deionized water4CFU/ml, 1ml was placed on a panel and an area of approximately 5cm by 5cm was coated continuously with a hand held applicator for a contact time of 1 minute. The cultures were immediately recovered from the plate with a swab and transferred to a general purpose bottle containing the neutralising agent (1ml) and maximum recovery diluent (9 ml). A10-fold serial dilution was prepared, and 0.1ml aliquots of the dilution were spread on nutrient agar and the experiment repeated. Plates were incubated at 37 ℃ for 24 hours and 48 hours, and read using conventional techniques. This procedure was then repeated with the culture but with a contact time of 5 minutes. All four samples were subjected to the same protocol.
TABLE 5 results
| Sample(s) | Contact time 1 minute (CFU/ml) | Contact time 5 minutes (CFU/ml) |
| S1 | 52 | 30 |
| S2 | 2.1×102 | 1.6×102 |
| S3 | 97 | 31 |
| S4 | 4.1×102 | 1.9×102 |
Discussion of the related Art
The test specimens (S1 and S3) caused a significant reduction in the number of bacteria (from 1.5 × 10) at 1 minute contact time3CFU/ml), the reduction was less after 5 minutes. Complete killing of the bacteria was not achieved with 5 minutes of contact.
The control samples (S2 and S4) caused a significant but small reduction in the number of bacteria (from 1.5X 10) at 1 minute and 5 minute contact times3CFU/ml). This may be due primarily to the difficulty in recovering the culture from the plate using a wiping technique and drying the culture during the continuous spreading on the plate.
Conclusion
PVC94 laminates treated with 2 vol% antimicrobial composition were effective in reducing MRSA bacterial levels when contacted for a short period in aqueous media.
These coatings may be very effective in controlling MRSA bacterial contamination in hospitals and similar environments.
Example 8 antimicrobial efficacy determination of coated test plaques containing the antimicrobial composition of example 1
The test microorganisms were:
bacillus subtilis NCTC44878 3.2×106CFU/ml
Pseudomonas aeruginosa NCTC 106623.6X 106CFU/ml
Method of producing a composite material
The test panels were coated with a paint/powder coating containing the antimicrobial composition of example 1. The coated test plates were challenged with broth cultures of the two organisms at the above concentrations for a contact time of 10 minutes.
The bacterial suspension was pipetted onto the coated test plate and wiped off with a swab after 10 minutes. Swabs were transferred to maximum recovery diluent and plated onto standard plate count agar, incubated at 30 ℃ for 24 hours, and the total number of colonies was counted.
Results
TABLE 6 paint coatings
| Plate number | Bacillus subtilis (CFU/ml) | Pseudomonas aeruginosa (CFU/ml) |
| 1 | 20 | 32 |
| 2 | 7 | 3 |
| 3 | TNC | TNC |
| 4 | 60 | 15 |
| 5 | 83 | 41 |
| 6 | TNC | TNC |
TABLE 7 epoxy gloss powder coatings
| Plate number | Bacillus subtilis (CFU/ml) | Pseudomonas aeruginosa (CFU/ml) |
| 1 | TNC | TNC |
| 2 | TNC | 286 |
| 3 | TNC | 132 |
| 4 | 30 | 9 |
| 5 | 150 | 24 |
| 6 | 42 | 30 |
TABLE 8 Gray epoxy polyester gloss powder coatings
| Plate number | Bacillus subtilis (CFU/ml) | Pseudomonas aeruginosa (CFU/ml) |
| 1 | 4 | 13 |
| 2 | 10 | 9 |
| 3 | 6 | 5 |
| 4 | TNC | TNC |
| 6 | TNC | TNC |
Too much TNC to count
Conclusion
The results show that bacteria are almost completely eradicated by the antimicrobial composition of example 1 in a variety of paint/powder coating formulations within a 10 minute contact time, even if the surface is dry.
Thus, a powder coating containing the antimicrobial composition of example 1 in concentrations that proved effective may be very effective in reducing the number of bacteria on a surface in a short period of time.
Example 9 efficacy of the antimicrobial composition "LCF" of example 2
The test samples were as follows:
1000 LCF: 1% by volume aqueous LCF solution
2000 LCF: 2% by volume aqueous LCF solution
3000 LCF: 3% by volume aqueous LCF solution
The microorganisms used were:
legionella pneumophila NCTC11192
Escherichia coli NCTC9001
Staphylococcus aureus NCIMB12702
Salmonella enteritidis NCTC5188
Listeria monocytogenes type 1 NCTC7973
Pseudomonas aeruginosa NCIMB12469
Method of producing a composite material
The European Suspension Test (Pr En 12761995, 11 months) was performed under the following experimental conditions:
test concentration: pure (C)
Test temperature: 10 deg.C (+/-1 deg.C)
The test conditions are as follows: clean (0.3g/100ml bovine albumin)
Dirty (3g/100ml bovine albumin)
Neutralizing agent: 3g/l lecithin, 8030 g/l polysorbate, 5g/l sodium thiosulfate, 1g/l L histidine, 30g/l saponin in diluent
Contact time: 5 minutes
The culture temperature is as follows: 37 deg.C (+/-1 deg.C)
Results
For the test results to be effective, the neutralizing agent used must prove to be non-toxic to the bacteria and sufficient to neutralize the tested product. The test conditions must also be effective.
To pass the test, it must be demonstrated that a product diluted with hard water results in a viable count reduction of at least 10 when tested under simulated clean or dirty conditions and under the required test conditions5。
Results for LCF of tables 9-1000
| Test organisms | Log reduction of cleaning conditions | Pass/fail | Dirty condition log reduction | Pass/fail |
| Legionella pneumophila | 4.12 | Failure of | 3.94 | Failure of |
| Escherichia coli | 4.26 | Failure of | 4.02 | Failure of |
| Staphylococcus aureus | 4.08 | Failure of | 4.10 | Failure of |
| Salmonella enteritidis | 4.44 | Failure of | 4.08 | Failure of |
| Listeria monocytogenes | 4.54 | Failure of | 4.20 | Failure of |
| Pseudomonas aeruginosa | 4.02 | Failure of | 3.90 | Failure of |
Results for LCF of tables 10-2000
| Test organisms | Log reduction of cleaning conditions | Pass/fail | Dirty condition log reduction | Pass/fail |
| Legionella pneumophila | 4.68 | Failure of | 4.62 | Failure of |
| Escherichia coli | 4.76 | Failure of | 4.34 | Failure of |
| Staphylococcus aureus | 4.68 | Failure of | 4.22 | Failure of |
| Salmonella enteritidis | 4.72 | Failure of | 4.28 | Failure of |
| Listeria monocytogenes | 4.86 | Failure of | 4.30 | Failure of |
| Pseudomonas aeruginosa | 4.64 | Failure of | 4.10 | Failure of |
Results for LCF of tables 11-3000
| Test organisms | Log reduction of cleaning conditions | Pass/fail | Dirty condition log reduction | Pass/fail |
| Legionella pneumophila | 4.84 | Failure of | 4.68 | Failure of |
| Escherichia coli | 4.72 | Failure of | 4.27 | Failure of |
| Staphylococcus aureus | 4.84 | Failure of | 4.44 | Failure of |
| Salmonella enteritidis | 4.92 | Failure of | 4.95 | Failure of |
| Listeria monocytogenes | 4.98 | Failure of | 4.54 | Failure of |
| Pseudomonas aeruginosa | 4.79 | Failure of | 4.62 | Failure of |
Conclusion
At 10 ℃, none of the three samples 1000LCF, 2000LCF and 3000LCF passed the European sustension Test for all microorganisms used. However, although the above samples failed this rigorous test, they did show significant antimicrobial activity against all microorganisms.
Example 10 efficacy of the antimicrobial composition of example 1, "D4L
The test samples were as follows:
500D 4L: 0.5 vol% D4L aqueous solution
1000D 4L: 1.0% by volume aqueous D4L solution
1500D 4L: 1.5 vol.% D4L aqueous solution
2000D 4L: 2.0% by volume aqueous D4L solution
The microorganisms used were:
legionella pneumophila NCTC11192
Escherichia coli NCTC9001
Staphylococcus aureus NCIMB12702
Salmonella enteritidis NCTC5188
Listeria monocytogenes type 1 NCTC7973
Pseudomonas aeruginosa NCIMB12469
Method of producing a composite material
The European Suspension Test was performed under the following experimental conditions:
test concentration: pure (C)
Test temperature: 10 deg.C (+/-1 deg.C)
The test conditions are as follows: clean (0.3g/100ml bovine albumin)
Dirty (3g/100ml bovine albumin)
Neutralizing agent: 3g/l lecithin, 8030 g/l polysorbate, 5g/l sodium thiosulfate, 1g/l L histidine, 30g/l saponin in diluent
Contact time: 5 minutes
The culture temperature is as follows: 37 deg.C (+/-1 deg.C)
Results
For the test results to be effective, the neutralizing agent used must prove to be non-toxic to the bacteria and sufficient to neutralize the tested product. The test conditions must also be effective.
To pass the test, it must be demonstrated that a product diluted with hard water results in a viable count reduction of at least 10 when tested under simulated clean or dirty conditions and under the required test conditions5。
Results of tables 12-500D4L
| Test organisms | Log reduction of cleaning conditions | Pass/fail | Dirty condition log reduction | Pass/fail |
| Legionella pneumophila | 4.64 | Failure of | 4.48 | Failure of |
| Escherichia coli | 4.76 | Failure of | 4.55 | Failure of |
| Staphylococcus aureus | 4.80 | Failure of | 4.70 | Failure of |
| Salmonella enteritidis | 4.82 | Failure of | 4.75 | Failure of |
| Listeria monocytogenes | 4.89 | Failure of | 4.72 | Failure of |
| Pseudomonas aeruginosa | 4.50 | Failure of | 4.36 | Failure of |
Results of tables 13-1000D4L
| Test organisms | Log reduction of cleaning conditions | Pass/fail | Dirty condition log reduction | Pass/fail |
| Legionella pneumophila | 6.10 | By passing | 5.64 | By passing |
| Escherichia coli | 6.42 | By passing | 5.85 | By passing |
| Staphylococcus aureus | 6.10 | By passing | 5.58 | By passing |
| Salmonella enteritidis | 5.98 | By passing | 5.92 | By passing |
| Listeria monocytogenes | 6.72 | By passing | 6.27 | By passing |
| Pseudomonas aeruginosa | 5.88 | By passing | 5.21 | By passing |
Results of tables 14-1500D4L
| Test organisms | Log reduction of cleaning conditions | Pass/fail | Dirty condition log reduction | Pass/fail |
| Legionella pneumophila | 6.88 | By passing | 6.14 | By passing |
| Escherichia coli | 7.14 | By passing | 7.02 | By passing |
| Staphylococcus aureus | 6.98 | By passing | 6.34 | By passing |
| Salmonella enteritidis | 6.52 | By passing | 6.40 | By passing |
| Listeria monocytogenes | 7.39 | By passing | 6.83 | By passing |
| Pseudomonas aeruginosa | 6.45 | By passing | 6.06 | By passing |
Results of tables 15-2000D4L
| Test organisms | Log reduction of cleaning conditions | Pass/fail | Dirty condition log reduction | Pass/fail |
| Legionella pneumophila | 7.22 | By passing | 6.48 | By passing |
| Escherichia coli | 7.20 | By passing | 7.12 | By passing |
| Staphylococcus aureus | 7.34 | By passing | 7.08 | By passing |
| Salmonella enteritidis | 7.12 | By passing | 6.62 | By passing |
| Listeria monocytogenes | 7.59 | By passing | 7.36 | By passing |
| Pseudomonas aeruginosa | 6.78 | By passing | 6.32 | By passing |
Conclusion
At 10 ℃, for all microorganisms used in the experiment, three samples 1000D4L, 1500D4L, and 2000D4L all passed the European sustension Test. Under the same conditions, 500D4L failed the test.
The test results of comparative examples 9 and 10 demonstrate that composition "D4L" is more effective than composition "LCF". Composition "D4L" contained an antimicrobial agent that was more polar than the antimicrobial agent in composition "LCF". The inclusion of a polar antimicrobial agent can enhance the effectiveness of the composition.
Example 12 dissociation of antimicrobial composition "D4L" of example 1 after immersion in water
This example is to evaluate the difference in biofilm growth on experimental and control surfaces after 48 hours of submersion in water. The experimental surface was coated with the antimicrobial composition, while the control surface was not coated.
Method of producing a composite material
Eight aluminum bottles were painted with four different paints. The paint types were the series 1 to 4 as described below. Four bottles were painted with a paint containing 2% by weight of the antimicrobial composition of example 1 and four bottles were painted with a standard paint and used as a control.
The paint types were as follows:
series 1: gloss of the K type (tough, durable enamels for high quality industrial finishes and decorative interior/exterior wood)
Series 2: matt white latex (for interior/exterior decoration, preservative for protecting cans against microbial spoilage)
Series 3: blue Hydracoat (water-soluble substitute for synthetic alkyd enamel for toy and model coatings)
Series 4: aquaguard (two-pack epoxy coating for walls and floors).
The bottles were placed into the inoculated solution, capped and incubated for 48 hours. The bottles were then removed and sprayed with 0.5% tween/phosphate buffer (100ml) to remove all biofilm that had formed. Ten-fold serial dilutions were prepared by plating the resulting solution onto plates, using Miles and Misra Total VibleCount Technique and incubated overnight at 37 ℃ in an inverted position. The number of Colony Forming Units (CFU) was then counted (considered as viable individuals) and the test and control plates were compared.
Results
Biofilm growth recovered after 24 hours-E.coli
Series 1: growth on the test plates was 50% greater than the control.
Series 2: there was no growth on the test plates and very little growth on the control.
Series 3: growth on the test plates was 25% greater than the control.
Series 4: growth on the test plates was 43% greater than the control.
Biofilm growth recovery after 24 hours-Pseudomonas aeruginosa
Series 1: growth on the test plates was 50% greater than the control.
Series 2: very little growth was observed on the test plates, and no growth was observed on the control.
Series 3: growth on the test plates was 25% greater than the control.
Series 4: growth on the test plates was 20% greater than the control.
The components of the antimicrobial composition dissociate and dissolve in the surrounding solution, providing a carbon source for the microbial population. The results show that the growth of microorganisms on the treated material increased after 24 hours of immersion in the microbial broth. This indicates that the paints containing the antimicrobial composition of the invention are more nutritious than the control and that the antimicrobial composition is biodegradable.
Example 13 Low leacheate toxicity
Method of producing a composite material
Four different surface coatings, paint series 1-4 described in example 12, were applied to an aluminum substrate. And then compared to a control without the antimicrobial composition.
The microorganisms used were Escherichia coli and Pseudomonas aeruginosa.
After 24 hours, the aluminum panels were rinsed with deionized water and the washes were tested with a Microtox test. This test uses the genus Fluorovibrio (a bioluminescent microorganism) which is very sensitive to the action of toxins. In Microtox Test, the sample is mixed with live bacteria that are sensitive to toxic compounds. The mixture was adjusted for a short period and the luminescence was read. In the presence of substances in concentrations that are highly toxic and harmful to humans, bacteria are damaged and stop emitting light. Thus the greater the luminescence loss of the sample, the higher the toxicity of the sample.
Results
FIGS. 1 and 2 show the recovered residual Pseudomonas aeruginosa and Escherichia coli biofilms on the test and control samples, respectively, after 24 hours. From FIGS. 1 and 2, it is apparent that the biofilm formation on the control samples is greater.
FIGS. 3 and 4 show the toxicity of the surface leacheate of Pseudomonas aeruginosa and Escherichia coli in the test sample and the control sample, respectively. The control samples had a less toxic leacheate than the test samples. However, the leachates of both the test and control samples showed low toxicity.
Effective concentration values (EC50) for 50% of the population suffering from an adverse effect were difficult to calculate, and lethal median values (LD50) could not be calculated.
The leacheate effect of some antimicrobial compositions was similar to other test paint controls. For example, paint series 1 containing the antimicrobial composition had similar experimental results as paint series 3 without the composition of the present invention. Different products of the same type (i.e. paint) thus gave different results in the Microtox test on leachates. This indicates that the antimicrobial composition of the invention has only a minor effect on the toxicity of the leacheate, which is within the normal range of antimicrobial-free products, and therefore the leacheate is low-toxic and safe.
The low toxicity of the leacheate of the composition of the invention is environmentally very desirable.
Example 14 antimicrobial testing of coated plaques
Steel panels were tested with a coating containing 0% by volume (as a control), 1.5%, 2.0% and 3.0% by volume of the antimicrobial composition of example 1.
The microorganisms used were:
methicillin resistant golden yellow NCTC 1940/2.1X 105CFU/ml
Staphylococcus (MRSA)
Pseudomonas aeruginosa NCIMB 12469/2.9X 105CFU/ml
Escherichia coli NCTC 9001/2.2X 105CFU/ml
Method of producing a composite material
Selected microorganisms (0.1ml) were transferred to each coated steel plate. Sterile plastic sheets 5cm x 5cm) were placed on the microorganisms, which were then carefully spread to fill the area covered by the plastic sheets.
Immediately after completion of the above steps-the first set of samples was processed at 0 minutes.
The plastic sheet is removed and placed on the tile to ensure that the surface that has contacted the contaminated steel plate is uppermost. The exposed surface was then swabbed to remove all micro-organisms and the swab was transferred to 10ml of Maximum Recovery Diluent (MRD). A second swab was used to wipe the contaminated area on the surface of the steel plate. The swab was also transferred to the same MRD bottle and the bottle was left for 10 minutes to ensure that the swab was sufficiently soaked. The vial was then thoroughly spin-mixed (whirlimix) for 10 seconds.
The resulting mixture (0.1ml) was then transferred to nutrient agar plates, which were incubated at 37 ℃ for 48 hours.
The above procedure was repeated for the other two groups of samples after 30 minutes and 16 hours of contact at 25 ℃.
Results
The results of the tests performed on the coated panels are detailed in tables 16, 17 and 18. The results in table 16 should be taken as a base to compare with the results obtained after 30 minutes and 16 hours. However, it is clear from the differences that the recovery of contaminating microorganisms is not very stable.
TABLE 16-0 min (counts per plate)
| Sample(s) | 1.5％ | 2.0％ | 3.0％ | Control |
| MRSA | 99116101 | 79100107 | 13111180 | 10290122 |
| Escherichia coli | 105100138 | 9811086 | 1188869 | 142108127 |
| Pseudomonas aeruginosa | 103152 | 10097 | 139110 | 115107 |
| 112 | 1 36 | 87 | 128 |
TABLE 17-30 min (counts per plate)
| Sample(s) | 1.5％ | 2.0％ | 3.0％ | Control |
| MRSA | 9162 | 100 | 000 | 796684 |
| Escherichia coli | 7412 | 012 | 130 | 918770 |
| Pseudomonas aeruginosa | 181116 | 41410 | 595 | 10397111 |
Tables 18-16 hours (counts on each plate)
| Sample(s) | 1.5％ | 2.0％ | 3.0％ | Control |
| MRSA | 210 | 000 | 000 | 654451 |
| Escherichia coli | 000 | 000 | 000 | 394122 |
| Pseudomonas aeruginosa | 000 | 000 | 000 | 795961 |
Conclusion
The results in table 17 show that the antimicrobial effect of the antimicrobial composition is evident even after 30 minutes of contact. The consistently higher counts obtained from the control plates provide evidence for this. Furthermore, the significant difference between the counts of the test panels containing 1.5% by volume antimicrobial composition and the test panels containing 2.0% by volume and 3.0% by volume antimicrobial composition again demonstrates the antimicrobial effect of the compositions of the present invention.
The counts after 16 hours of contact detailed in table 18 also support the antimicrobial effect of the antimicrobial composition, although consistently lower control numbers suggest that there may have been a drying effect during the incubation period.
The results demonstrate that the antimicrobial composition of the present invention provides antimicrobial action to the board coating, producing the most effective kill when containing 2.0 vol% or more of the antimicrobial composition.
Claims (28)
1. An antimicrobial composition consisting essentially of:
(i) at least one first antimicrobial agent having a surface tension of 20-35mN/m at 20 ℃ and selected from (a) quaternary ammonium compounds having the general formula R1R2R3R4N+X-Wherein one or two R groups are alkyl substituted by aryl or interrupted by aryl or oxygen, the other R groups are identical or different and are C1-C4Alkyl, (b) a dialkyldimethylammonium compound wherein the two non-methyl alkyl groups are selected from C8-C12Alkyl, and (c) halobenzalkonium or aromatic ring-substituted halobenzalkonium;
(ii) at least one compound having a surface tension of 8-14mN/m at 20 ℃ and being a siloxane;
(iii) at least one polar solvent; and
(iv) at least one additional antimicrobial agent;
wherein the antimicrobial composition is used to reduce or control the formation of microbial colonies on a surface to which the composition is applied.
2. An antimicrobial composition according to claim 1, wherein the surface tension of the at least one compound (ii) is 10 mN/m.
3. An antimicrobial composition according to claim 1, wherein said at least one compound (ii) is at least one polysiloxane.
4. An antimicrobial composition according to claim 3, wherein the polysiloxane is selected from the group consisting of polydimethylsiloxane and polydimethylhydroxysiloxane.
5. An antimicrobial composition according to claim 4 wherein the polysiloxane is selected from the group consisting of having C12-C20Polydimethylsiloxane of chain length and having C12-C20Chain length polydimethyl hydroxy siloxane.
6. An antimicrobial composition according to claim 1, wherein the at least one first antimicrobial agent and/or the at least one additional antimicrobial agent is polar.
7. An antimicrobial composition according to claim 1, comprising at least one antimicrobial agent selected from the group consisting of bactericides, fungicides, algicides, bactericides and moldicides.
8. An antimicrobial composition according to claim 1, wherein said first antimicrobial agent is selected from the group consisting of N-dodecyl-N, N-dimethyl benzalkonium chloride and benzyl-C12-C16-alkyldimethyl-ammonium chloride.
9. An antimicrobial composition according to claim 1, wherein the at least one additional antimicrobial agent is selected from the group consisting of amphoteric compounds, iodine-carrying compounds, phenolic compounds, quaternary ammonium compounds, hypochlorites and nitrogen-based heterocyclic compounds.
10. The antimicrobial composition of claim 9, wherein the phenolic compound is selected from the group consisting of methyl, ethyl, butyl, halogen, and aryl substituted phenols
11. The antimicrobial composition of claim 9, wherein the phenolic compound is selected from the group consisting of 2-phenylphenol, 2-benzyl-4-chlorophenol, 2-cyclopentanol-4-chlorophenol, 4-tert-amylphenol, 4-tert-butylphenol, 4-chloro-2-pentylphenol, 6-chloro-2-pentylphenol, p-chloro-m-xylenol, 2, 4, 4-trichloro-2-hydroxydiphenol, thymol, 2-isopropyl-3-methylphenol, chlorothymol, 3-methyl-4-chlorophenol, 2, 6-dichloro-4-n-alkylphenol, 2, 4-dichloro-m-xylenol, 2-chloro-4-methylphenol, 2-methyl-2-ethylphenol, and mixtures thereof, 2, 4, 6-trichlorophenol and 2-benzyl-4-chlorophenol.
12. The antimicrobial composition of claim 9, wherein the amphoteric compound is selected from the group consisting of dodecyl beta-alanine, dodecyl beta-aminobutyric acid, dodecylamino-bis (aminoethylamino) glycine, and N- (3-dodecylamino) propylglycine.
13. The antimicrobial composition of claim 9, wherein the iodine-carrying compound is selected from the group consisting of complexes of iodine or triiodine with polyvinylpyrrolidone, polyether glycol, polyvinyl alcohol, polyacrylates, polyamides, polyalkylenes, and polysaccharides.
14. The antimicrobial composition of claim 9, wherein the hypochlorite is selected from alkali metal and alkaline earth metal hypochlorites.
15. The antimicrobial composition of claim 14, wherein the hypochlorite is selected from the group consisting of lithium, sodium, potassium, and calcium hypochlorites.
16. The antimicrobial composition of claim 1 comprising trisodium chlorophosphate and hydrates thereof, chlorine dioxide or its precursors, derivatives of N, N-dichloro-4-carboxybenzenesulfonamide, 1, 3-dichloro-5, 5-dimethylhydantoin or chloroisocyanuric acid.
17. The antimicrobial composition of claim 9, wherein the nitrogen-based heterocyclic compound is selected from the group consisting of pyridine derivatives, triazoles, thiazoles, and imidazoles.
18. The antimicrobial composition of claim 17, wherein the nitrogen-based heterocyclic compound is selected from the group consisting of 4-pyridinecarboxylic acid hydrazide, sodium 2-pyridinethiol, and bis (2-pyridinethio) zinc-1, 1-dioxide.
19. An antimicrobial composition according to claim 1, containing 1-4 vol.% of the at least one compound (ii).
20. The antimicrobial composition of any one of claims 1-19, wherein the at least one polar solvent is selected from the group consisting of water, isopropanol, diethylene glycol, and dipropylene glycol.
21. The antimicrobial composition of claim 1, containing 1-70 vol% of the polar solvent.
22. A formulation comprising the antimicrobial composition of any one of claims 1 to 21 and a material selected from the group consisting of plastics, fibers, coatings, films, laminates, adhesives, sealants, clays, porcelains, china clay, concrete, sand, paints, varnishes, lacquers, cleaners and fixable or curable compositions.
23. A formulation according to claim 22, wherein the formulation contains from 0.1 to 5.0% by weight of the antimicrobial composition.
24. A formulation according to claim 23, wherein the formulation contains from 0.5 to 2.0% by weight of the antimicrobial composition.
25. A method for reducing or controlling the formation of microbial colonies on a surface, the method comprising applying the antimicrobial composition of any one of claims 1 to 21 or the formulation of any one of claims 22 to 24 to the surface.
26. Use of the antimicrobial composition of any one of claims 1 to 21 or the formulation of any one of claims 22 to 24 to reduce or control the formation of microbial colonies on a surface to which the composition or formulation is applied.
27. A method of making an antimicrobial composition according to any one of claims 1 to 21, the method comprising the steps of: (i) mixing together the antimicrobial agents, (ii) adding the at least one compound (ii) to the mixture of step (i), (iii) adding the polar solvent to the mixture of step (ii), and (iv) stirring the resulting mixture until a clear solution is formed.
28. A method of making a formulation according to any one of claims 22 to 24, comprising the step of adding the antimicrobial composition of any one of claims 1 to 21 to the materials listed in claim 22.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0100155.1 | 2001-01-04 | ||
| GB0100155A GB2374011C (en) | 2001-01-04 | 2001-01-04 | Anti-microbial composition |
| US09/756,457 US20020137631A1 (en) | 2001-01-04 | 2001-01-08 | Anti-microbial composition |
| US09/756,457 | 2001-01-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HK1101109A1 HK1101109A1 (en) | 2007-10-12 |
| HK1101109B true HK1101109B (en) | 2012-03-16 |
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