Antibacterial composition

Abstract

The present invention relates to antimicrobial compositions, more particularly to personal care compositions such as soap bars, and more particularly to compositions comprising essential oil compounds and tetrahydroxyalkyleneamine compounds that interact synergistically to provide a desired result.

Description

[Technical field]

[0001] The present invention relates to antibacterial compositions.More particularly, the present invention relates to personal care compositions, such as personal care compositions for hair, body, hand or face care, which provide antibacterial benefits.More particularly, the present invention relates to cleansing compositions that contain actives that interact to provide synergistic antibacterial efficacy and provide protection against bacteria between two washes. [Background technology]

[0002] The present invention is useful for cleaning any part of the body, but is particularly directed to antimicrobial compositions suitable for hand hygiene or body or face washing.

[0003] Hand washing with antibacterial soap, especially after using the toilet and / or before eating food, has been identified as one of the most effective ways to improve human mortality, morbidity and general quality of life. Hygiene and disinfectant soap compositions containing chlorine-based antibacterial agents, such as triclosan, are known. If a user uses a soap with low or slow antibacterial activity, the user's skin is likely to be relatively inadequately de-bacterized, which may cause further contamination of animate and / or inanimate surfaces, leading to the spread of pathogens and resulting illness. Therefore, providing hand washing and body wash compositions with enhanced antibacterial activity is of paramount importance to provide consumers with improved health and quality of life.

[0004] Although the above problems are greatly alleviated by the use of compositions containing known antimicrobial actives, there is a need to ensure enhanced antimicrobial efficacy while at the same time ensuring that the skin is protected from bacteria between two washes.The inventors have found that this benefit can be obtained when certain essential oils are combined with selected tetrahydroxyalkyleneamine compounds.

[0005] International Publication No. WO06026170 (Bausch & Lomb) discloses compositions comprising an effective disinfecting amount of one or more antimicrobial agents and one or more (hydroxyalkyl)diamine buffers, (hydroxyalkoxy)diamine buffers, or combinations thereof.

[0006] To the applicant's knowledge, it has never been disclosed that the essential oil compounds claimed in this invention in combination with selected tetrahydroxyalkyleneamine compounds exhibit a highly efficient antibacterial action while also providing protection to the skin against bacteria that may attack the skin between two washing operations. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. WO06026170 Brochure Summary of the Invention [Problem to be solved by the invention]

[0008] It is therefore an object of the present invention to provide an antimicrobial composition that exhibits enhanced antimicrobial activity long after the skin has been washed with the composition.

[0009] Another object of the present invention is to provide an antimicrobial composition that is effective when used in personal cleansing compositions, especially those that contain soap.

[0010] It is yet another object of the present invention to provide an antimicrobial composition that is effective against bacterial infestation for an extended period of time after the skin has been washed with the composition. [Means for solving the problem]

[0011] According to a first aspect of the present invention there is provided an antimicrobial composition comprising: (i) A compound of the following general formula 1: [ka] [wherein R1 to R4 are each independently a straight or branched carbon chain having 2 to 5 carbon atoms; and R5 is a carbon chain having 1 to 4 carbon atoms]; and (ii) an essential oil compound of general formula 2 having the structure [ka] [In the formula, R1 is H, OH, or OR, where R is an alkyl chain having 1 to 5 carbon atoms; R2 is a C1 to C6 straight chain alkyl group; or a C3 to C6 branched alkyl group; or a C5 to C6 cyclic or heterocyclic alkyl group; or a C6 aromatic group.

[0012] A second aspect of the invention relates to a method of providing antimicrobial efficacy to skin comprising the steps of applying a composition of the first aspect to a desired skin surface and then wiping the composition off the surface or rinsing the surface with water to render it substantially free of the composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] These and other aspects, features and advantages will become apparent to those skilled in the art upon reading the following detailed description and the appended claims. For the avoidance of doubt, any feature of one aspect of the present invention can be utilized in any other aspect of the present invention. The term "comprising" is intended to mean "including" but not necessarily "consisting of" or "composed of"; in other words, the listed steps or options need not be exhaustive. It should be noted that the examples given in the following description are intended to clarify the invention, but are not intended to limit the invention to those examples themselves. Similarly, all percentages are weight / weight percentages unless otherwise indicated. Except in the examples and comparative examples, or unless otherwise expressly indicated, all numbers in the present specification and claims indicating quantities, physical properties of materials and / or use of materials or reaction conditions should be understood to be modified by the word "about". Numerical ranges expressed in the format "from x to y" are understood to include x and y. When multiple preferred ranges for a particular feature are expressed in the format "from x to y," it is understood that all ranges combining the different endpoints are also contemplated. In other words, in specifying any range of values, any particular upper limit value can be associated with any particular lower limit value.

[0014] The disclosure of the invention found herein should be considered to cover all embodiments found in the claims as having multiple dependencies on each other, notwithstanding the fact that the claims may be found without multiple dependencies or overlaps.

[0015] Where features are disclosed with respect to a particular embodiment of the invention (e.g., a composition of the invention), such disclosure should be considered to apply mutatis mutandis to any other embodiment of the invention (e.g., a method of the invention).

[0016] As used herein, "antimicrobial composition" is meant to include compositions for topical application to the skin, hair and / or scalp of mammals, particularly humans. Such compositions are generally applied to the desired topical surface of the body for a period of time ranging from a few seconds to a few minutes. If the application time is short, e.g., on the order of a few seconds to a few minutes, and the composition is then rinsed or wiped off with water, such compositions are known as cleansing or wash-off compositions. If the composition is applied for a longer period, e.g., from a few minutes to up to 24 hours, and is washed off during the normal process of personal cleaning, such compositions are known as leave-on compositions. The composition according to the invention may be of the wash-off or leave-on type. Of these two, the wash-off type is preferred. It includes any product that is applied to the human body to improve appearance, cleansing, odor control or even general aesthetics. The composition of the present invention may be in the form of a liquid, lotion, cream, foam, scrub, gel, bar, shampoo, conditioner, hand wash, face wash or body wash product. It is more preferably used to disinfect hands or other parts of the human body.

[0017] The present invention more particularly relates to antimicrobial cleansing compositions.

[0018] The antibacterial compositions of the present invention comprise a compound of general formula 1: [ka] [In the formula, R1 to R4 are each independently a straight or branched carbon chain having 2 to 5 carbon atoms, and R5 is a carbon chain having 1 to 4 carbon atoms.]

[0019] R1 to R4 are preferably carbon chains having 3 or 4 carbon atoms, more preferably 3 carbon atoms. R5 is preferably a carbon chain having 2 or 3 carbon atoms, more preferably 2 carbon atoms. More preferably, R5 is a linear carbon chain.

[0020] The most preferred compound of formula 1 is tetrahydroxypropylethylenediamine (THPE), which has the formula: [ka]

[0021] The compound of formula 1 is preferably contained in an amount of 0.1 to 10% by weight, more preferably 0.1 to 5% by weight, and even more preferably 0.2 to 3% by weight of the composition.

[0022] The compositions of the present invention include an essential oil compound of general formula 2, having the following structure: [ka] [In the formula, R1 is H, OH, or OR, where R is an alkyl chain having 1 to 5 carbon atoms; R2 is a C1 to C6 straight chain alkyl group; or a C3 to C6 branched alkyl group; or a C5 to C6 cyclic or heterocyclic alkyl group; or a C6 aromatic group.

[0023] The most preferred essential oil compounds according to the compound of formula 2 for use in the compositions of the present invention are selected from thymol, carvacrol, (E)-2(prop-1-enyl)phenol, 2-propylphenol, 4-pentylphenol, 4-sec-butylphenol, 2-benzylphenol or eugenol, or combinations thereof.

[0024] The structures of these compounds are shown below:

[0025] The structure of thymol is shown below: Timor [ka]

[0026] Carvacrol [ka]

[0027] (E)-2(Prop-1-enyl)phenol [ka]

[0028] 2-Propylphenol [ka]

[0029] 4-Pentylphenol [ka]

[0030] 4-sec-Butylphenol [ka]

[0031] 2-Benzylphenol [ka]

[0032] Eugenol [ka]

[0033] Of the above essential oil compounds, thymol, carvacrol or eugenol are more preferred for use in the compositions of the present invention.

[0034] The essential oil compound is contained in an amount of 0.001 to 1% by weight, preferably 0.005 to 1% by weight, and more preferably 0.005 to 0.5% by weight of the composition.

[0035] It is further preferred that an additional essential oil compound of the terpene group is included in the composition of the present invention.The most preferred compound of the terpene group is terpineol.The terpineol is preferably selected from α-terpineol, β-terpineol, γ-terpineol or mixtures thereof.It is particularly preferred that the terpineol is α-terpineol.The terpineol can be added to the antimicrobial composition in a purified form.

[0036] The structure of the terpineol compound is shown below: [ka]

[0037] The antibacterial composition preferably contains 0.01 to 1% terpineol by weight of the composition, more preferably 0.05 to 0.5% terpineol.

[0038] According to a particularly preferred embodiment of the invention, the composition comprises a mixture of thymol and terpineol.

[0039] Without wishing to be bound by theory, the inventors believe that antimicrobial efficacy is achieved long after the washing step is completed as a result of deposition of active molecules on the skin. These molecules then interact with antimicrobial peptides already present on the skin between two washes to provide the desired benefit.

[0040] In the present invention, antibacterial alcohols (low molecular weight alcohols having 1 to 7 carbon atoms) are substantially absent. By substantially absent, it is meant that the concentration of alcohol is less than the amount required for antibacterial therapeutic activity. Preferably, antibacterial alcohols are present at less than 1%, more preferably less than 0.1%, and optimally, they are absent in the present invention.

[0041] The composition of the present invention preferably comprises a cosmetically acceptable base. According to one embodiment, the cosmetically acceptable base comprises water. According to another preferred embodiment, the base comprises a surfactant. Thus, the cosmetically acceptable base comprises water, a surfactant or a combination thereof. The cosmetically acceptable base may comprise an oil. A particularly preferred embodiment of the present invention comprises a cosmetically acceptable base that is an emulsion. In an emulsion, the oil and water are emulsified in the presence of an emulsifier, preferably a surfactant. The composition is preferably formulated as a cream, a lotion, a gel, a powder, an ointment, a body wash, a hand wash or a face wash product, a shampoo, a hair conditioner or a soap composition, preferably a soap bar. The product may be a body wash, a hand wash or a face wash product, most preferably a hand wash product.

[0042] The composition of the present invention can be used for skin cleansing, for example as a hand wash product. The antibacterial composition may further comprise a surfactant. When a surfactant is used, a particularly preferred surfactant is soap. Soap is a suitable surfactant for personal cleaning applications of the antibacterial composition of the present invention. The soap is preferably C8-C 24 Soap, more preferably C 10 -C 20 Soap, most preferably C 12 -C 18 It is a soap. The cation of the soap can be an alkali metal, an alkaline earth metal or ammonium. Preferably, the cation of the soap is selected from sodium, potassium or ammonium. More preferably, the cation of the soap is sodium or potassium.

[0043] A typical fatty acid blend will consist of 5-30% coconut fatty acids and 70-95% fatty acids by weight of the soap. Fatty acids derived from other suitable oils / fats such as peanut, soybean, tallow, palm, palm kernel, etc. may also be used in other desired proportions.

[0044] If present, the soap is preferably present in an amount of from 1 to 90%, preferably from 10 to 85%, more preferably from 25 to 75% by weight of the composition.

[0045] Other preferred surfactants are C8-C 22 and preferably, when the product is in liquid form, a C8-C 16 The surfactant is preferably selected from primary alkyl sulfates, secondary alkyl sulfonates, alkyl benzene sulfonates or ethoxylated alkyl sulfates. The composition may further comprise an anionic surfactant, such as an alkyl ether sulfate, preferably of natural or synthetic origin, having 1 to 3 ethylene oxide groups and / or sulfonic acid. Particularly preferred is sodium lauryl ether sulfate. Alkyl polyglucosides, preferably C6 to C8 16 Carbon chain lengths up to may also be present in the composition.

[0046] Preferred compositions may include other known ingredients such as fragrances, pigments, preservatives, emollients, sunscreens, emulsifiers, gelling agents, thickeners, etc. The selection of these ingredients will depend primarily on the type of composition.

[0047] Water is a preferred carrier. When water is present, it is preferably present at least 1% by weight of the composition, more preferably at least 2% by weight, even more preferably at least 5% by weight. When water is the carrier, a preferred liquid composition contains 10-99.8% by weight of water. The liquid antibacterial composition is useful as a skin disinfectant, for skin cleansing, especially for hand wash or face wash. When water is the carrier, a preferred solid composition contains 5-30% by weight of water.

[0048] The solid antimicrobial composition is preferably in the form of a molded solid, more preferably a bar. The solid antimicrobial composition is particularly useful for skin cleansing, especially for hand washes or face washes.

[0049] According to another embodiment, inorganic particulate materials are also suitable carriers. When inorganic particulate materials are carriers, the antimicrobial composition is in solid form. Preferably, the inorganic particulate material is talc. When the inorganic particulate material is talc, the solid antimicrobial composition is particularly useful as talc powder for application to face or body.

[0050] In another aspect of the invention, the compositions of the present invention are suitable for use in personal hygiene wipes.

[0051] The present invention also relates to a method of providing antimicrobial benefit to the skin, which method is preferably non-therapeutic or cosmetic in nature, comprising the step of applying a composition of the present invention to the desired skin surface.

[0052] This is followed by substantial removal of the composition from the surface after a specific time. Typically, people spend about 10 seconds to 2 minutes washing a body part, and it is expected that the desired antimicrobial activity should have occurred within this time frame. The washing time is preferably 10 seconds to 1 minute, more preferably 10 seconds to 30 seconds. Removal of the composition from the surface can be achieved by wiping the composition from the surface using a suitable wipe. Alternatively, it may be achieved by rinsing the surface with water so that it is substantially free of the composition. The composition is typically applied to the desired skin surface after diluting the composition with water. The composition can be diluted with water to a concentration of 1 to 50% by weight of the diluted solution, preferably 2 to 20% by weight.

[0053] The invention will now be described with reference to the following non-limiting examples. EXAMPLES

[0054] Example AC, 1: In vitro efficacy of THPE and thymol The following samples were tested for in vitro antimicrobial efficacy using the protocol described below: Example-A: Culture control Example B: 1% Tetrahydroxypropylethylenediamine (THPE) Example-C: 0.01% Thymol Example 1: 1% THPE + 0.01% Thymol

[0055] Protocol Solvents used: 10 mM sodium phosphate buffer for culture preparations at pH 7.4

[0056] Biology: Escherichia coli ATCC 10536

[0057] procedure: Test organisms were subcultured from glycerol stocks (stored at -70°C) onto TSA agar slants and incubated at 37°C for 18-24 hours. The slants were stored in the refrigerator for up to 2 weeks, after which new slants were prepared. The test organisms were streaked from the TSA slant onto a Petri dish plate containing TSA and incubated at 37°C for 21-22 hours before use. 10 in 10 mM sodium phosphate buffer 6 Bacterial inocula corresponding to the cells were prepared from the above plates. The OD of the culture was adjusted to 0.8 for E. coli and 10 8 cells / ml. Once, 10 8 When a bacterial inoculum corresponding to the cells is prepared in sodium phosphate buffer, it is 6 Serial dilutions were made onto the cells (1:10 dilution in 10 mM sodium phosphate buffer). For all treatments, 135 μl of bacterial inoculum (10 6 CFU / ml) was added to 300 μl reaction vessels (in microtiter plates / 96-well plates). For all controls and treatment groups, 15 μl of 100 mM buffer was added to give a final concentration equivalent to ~5 mM in all reactions. Each compound / active to be tested is added and brought to a volume of 300 μl with autoclaved distilled water. Note: Each treatment is tested in duplicate. The microtiter plates were incubated at 37°C for 4 hours (contact time) and then plated on TSA after the required serial dilutions in neutralizer D / E to test for bacterial killing. The plates were incubated overnight for E. coli testing. Colonies were counted to estimate the remaining bacteria and therefore the log kill.

[0058] The data on the mean bacterial survival (log cfu / ml) are summarized in Table 1: [Table 1]

[0059] The data in Table 1 above demonstrate that the combination of thymol and THPE provides a synergistic antibacterial effect compared to the individual compounds.

[0060] Examples D and 2: In vivo antibacterial efficacy of the compositions of the present invention in a soap base compared to a soap composition not containing any antibacterial active. The following two soap bars were prepared as shown in Table-2 below. [Table 2]

[0061] The above compositions were tested for in vivo antibacterial activity using the following protocol: 1. Each volunteer was given a soap bar that did not contain antibacterial active substances to use for bathing, washing hands, washing forearms, etc., and then washed off for 7 days before the start of the study. 2. Volunteers were instructed to refrain from using any leave-on products (sunscreens, hand sanitizers, skin moisturizers, lotions, creams, oils and antibacterial products) until the end of the study. 3. Volunteers were asked to come to the study site on the 8th day without washing their forearms in the morning (preferably without bathing). 4. On the eighth day, the researcher washed one forearm of the volunteer with the soap bar of Example D and the other forearm with the soap bar of Example 2. 5. The washing protocol was as follows: - Tap water temperature was 24℃±2℃. · Wet / soak in soapy water for 10 seconds. Moisten each forearm with tap water (100 ml ± 10 ml). · Apply soap back and forth 10 times along the length of your forearm. · Put 2-3ml of water into the palm of your gloved hand and lather your forearm with your hand for 30 seconds. Hold the foam on your forearm for 20 seconds. Wash your forearms under running tap water for 1 minute to remove all soap. Remove excess water by pat drying with sterile tissue paper. 30 minutes after washing your forearms, 8 Ten microliters of E. coli (10536) from the stock was applied to a defined circular area (7 cm) on the forearm skin. 2 (circle) for 10 minutes. 8 Culture stocks were prepared in 10 mM sodium phosphate buffer using 18-20 hour cultures. The OD was adjusted to 0.8 at 620 nm and the OD was adjusted to 0.8 at 10 8 The count was achieved. 6. After a 10-minute contact time of E. coli on the forearm skin, it was harvested by the cup scrub method (ASTM method, E2752-10) using 1.5 ml of extraction buffer. 7. Each sample was then serially diluted in 9 ml of D / E (Dey Engley Neutralizing Broth) and each dilution was plated onto MacConkey agar. 8. The plates were incubated at 37°C for 24 hours to allow E. coli growth, then colonies were counted and log cfu / ml was calculated using standard microbiological methods.

[0062] extraction buffer 0.4 g KH2PO4, 10.1 g Na2HPO4, 1.0 g Triton X100, 100.0 g Tween 80, and 11.67 g lecithin were dissolved in 1 liter of purified hot water. The final pH was adjusted to 7.8 ± 0.1. The buffer was vortexed immediately after autoclaving.

[0063] The data regarding bacteria remaining after the above treatments is summarized in Table 3 below: [Table 3]

[0064] The data in Table 3 above demonstrates that the soap bar composition of the present invention (Example 2) can provide much better antimicrobial efficacy compared to a conventional soap bar (Example D) long after the skin surface has been washed with the composition.

[0065] Examples EH and 3, 4: In vitro potency of THPE and carvacrol Similar experiments were performed with carvacrol + THPE as those performed with thymol + THPE. Antibacterial efficacy was measured in vitro as detailed above for Examples 1 and A-C. The antibacterial efficacy is summarized in Table-4 below:

[0066] [Table 4]

[0067] The data in Table-4 above show that similar synergistic activity is obtained for the combination of carvacrol and THPE compared to thymol+THPE.

[0068] Examples IK and 5: In vitro potency of eugenol and THPE Similar experiments to those performed with thymol+THPE were performed with eugenol+THPE. Antibacterial efficacy was measured in vitro as detailed above for Examples 1 and A-C. The antibacterial efficacy is summarized in Table-5 below: [Table 5]

[0069] The data in Table 5 above show synergistic activity for the combination of eugenol and THPE, although this effect is not as pronounced as for thymol+THPE.

Claims

1. 1. An antimicrobial composition comprising: (i) 0.1 to 10% by weight of a compound represented by the following general formula 1: 【Chemistry 1】 [In the formula, R １ ~R ４ are each independently a linear or branched carbon chain having 2 to 5 carbon atoms; R ５ is a carbon chain having 1 to 4 carbon atoms; and (ii) 0.005 to 0.5% by weight of an essential oil compound of general formula 2 having the following structure: 【Chemistry 2】 [In the formula, R １ is H, OH, or OR, where R is an alkyl chain having 1 to 5 carbon atoms; R ２ is C １ ~C ６ A straight chain alkyl group; or C ３ ~C ６ A branched alkyl group; or C ５ ~C ６ Cyclic or heterocyclic alkyl groups; or C ６ is an aromatic group; Contains provided that the essential oil compound is selected from thymol, carvacrol, 2-propylphenol, 4-pentylphenol, 4-sec-butylphenol, 2-benzylphenol, or eugenol, or a combination thereof; The compound of general formula 1 is tetrahydroxypropylethylenediamine (THPE) having the following formula: 【Chemistry 3】 and comprising a cosmetically acceptable base comprising water and a surfactant.

2. 2. The composition of claim 1, wherein the essential oil compound is thymol, carvacrol or eugenol.

3. The composition of claim 1 or 2, wherein the composition further comprises terpineol.

4. 4. The composition of claim 3, comprising a mixture of terpineol and thymol as essential oil compounds.

5. A composition according to any one of claims 1 to 4, wherein the surfactant is an anionic surfactant, preferably a soap.

6. The composition of any one of claims 1 to 5 in the form of a molded solid bar.

7. 7. A method of providing antimicrobial efficacy to skin comprising the steps of applying a composition according to any one of claims 1 to 6 to a desired skin surface, followed by wiping the composition off the surface or rinsing the surface with water to render it substantially free of the composition.

8. 8. The method of claim 7, wherein the composition is diluted with water before applying the composition to the desired skin surface.

9. The method of claim 8, wherein the composition is diluted with water to a concentration of 1 to 50%, preferably 2 to 20% by weight of the diluted solution.

10. The method of any one of claims 7 to 9, wherein the wiping or rinsing step is carried out 10 seconds to 2 minutes after applying the composition.

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