Therapeutic and non-therapeutic uses of personal cleansing compositions and methods of treatment

Abstract

A personal cleansing composition for use in a method of inhibiting or killing the growth of bacteria on human skin wherein the bacteria are selected from the group consisting of: Escherichia coli having a pH of up to or equal to 4 in solution, dermatobacterium acnes, and Corynebacterium minutus; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain, or an isomer thereof, or a mixture thereof, wherein the alkenyl chain comprises 18 to 20 carbon atoms.

Description

TECHNICAL FIELD

[0001] The present application relates generally to therapeutic and non-therapeutic uses of personal cleansing compositions; and treatment methods associated therewith. The personal cleansing compositions comprise salts of alkenyl sulfate esters having an alkenyl chain comprising from 18 to 20 carbon atoms. BACKGROUND

[0002] Human health is affected by a number of microbial entities or microorganisms, such as germs, bacteria, fungi, yeasts, molds, viruses, and the like. For example, infection by microbial entities or microorganisms including various viruses and bacteria results in a variety of diseases and ailments. To reduce such infections, people typically wash their skin with personal cleansing compositions. Personal cleansing compositions have traditionally been marketed in a variety of forms, such as bars, creams, lotions, and gels.

[0003] Washing with a personal cleansing composition, such as an antimicrobial soap, can remove dirt and germs from the skin. Removal of viruses and bacteria is due to the surfactant properties of the soap and the mechanical action of the washing process. Antimicrobial soaps generally include soap in combination with one or more active materials, such as antimicrobial agents; they can be in the form of a bar. When the skin is washed with an antimicrobial soap, such as a bar soap, the surfactant of the soap generally removes most of the microbial entities or microorganisms from the skin, while the antimicrobial agent is at least partially deposited onto the skin to provide residual protection against subsequent invasion.

[0004] Bacteria found on the skin can be divided into two groups: resident bacteria and transient bacteria. Resident bacteria are gram-positive bacteria that establish themselves as permanent colonies on the surface and outermost layers of the skin and play a relevant, helpful role in preventing colonization by other, more harmful bacteria and fungi.

[0005] Transient bacteria are bacteria that are not part of the normal resident flora of the skin, but can be deposited when air-borne contaminated material falls on the skin or when contaminated material comes into physical contact with the skin. Transient bacteria are generally divided into two subtypes: gram-positive bacteria and gram-negative bacteria. Gram-positive bacteria include pathogens such as Staphylococcus aureus Staphylococcus aureus ). Gram-negative bacteria include pathogens such as Escherichia coli Escherichia coli Gram-negative bacteria are generally distinguished from gram-positive bacteria by the presence of an additional protective cell membrane, which generally renders gram-negative bacteria less susceptible to topical antibacterial actives.

[0006] Antimicrobial cleansing products have been marketed in various forms for some time. Forms include deodorant soaps, antibacterial soaps, and surgical scrubs. These traditional rinse-off antimicrobial cleansing compositions have been formulated to provide bacterial reduction during washing.

[0007] A personal cleansing composition has been developed which comprises a water-soluble metal surfactant, such as sodium oleyl sulfate with or without lanthanum, see for example EP 0 018 019 A1.

[0008] Corynebacterium minutissimum is part of the Corynebacterium genus, which is the main pathogen of axillary malodor, the main malodor substrate of which is believed to originate from apocrine glands

[0009] There remains a need to formulate a personal cleansing composition that can be used to reduce axillary malodor.

[0010] Cutibacterium acnes (formerly known as Propionibacterium) is known to be associated with the skin acne condition, see for example US 2011 / 054039 A1.

[0011] Therefore, there remains a need to provide a personal cleansing composition that has anti-acne benefits.

[0012] Some antimicrobial cleansing compositions, especially surgical disinfectants, utilize significant levels of alcohols and / or harsh surfactants, which have been shown to dry and irritate skin tissue. An ideal personal cleanser should gently cleanse the skin, cause little or no irritation, and not leave the skin overly dry after frequent use, and preferably should provide a moisturizing benefit to the skin.

[0013] In general, personal cleansing compositions should meet many criteria for consumer acceptability. These criteria include cleansing effectiveness, skin feel, mildness to the skin and ocular mucosae, and lather volume. An ideal personal cleanser should gently cleanse the skin, cause little or no irritation, and not leave the skin overly dry after frequent use.

[0014] Therefore, there also remains a need to formulate a personal cleansing composition that provides mildness to the skin and has acceptable cleansing, lathering, or foaming performance. SUMMARY

[0015] A personal cleansing composition is provided for use in a method of inhibiting or killing the growth of bacteria on human skin, wherein the bacteria is selected from the group consisting of Escherichia coli, Cutibacterium acnes, and Corynebacterium minutissimum at a pH up to or equal to 4 in solution; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain, or an isomer thereof, or a mixture thereof, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms.

[0016] A personal cleansing composition for use in a method of treating acne and eradicating C. acnes on human skin; preferably facial skin; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof.

[0017] A personal cleansing composition for use in a method of treating axillary malodor and killing C. granulosum growing on human skin; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof.

[0018] A non-therapeutic use of a personal cleansing composition for gently cleansing the skin; preferably compared to a control composition comprising 10% by weight of sodium lauryl sulfate, 0.05% by weight of kathon CG, sufficient citric acid to give a pH of 5.5 ± 0.2 in sufficient water; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof.

[0019] A non-therapeutic use of a personal cleansing composition for preventing skin dryness; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof. DETAILED DESCRIPTION

[0020] Definitions of terms

[0021] In this document, unless otherwise specifically indicated otherwise, the following definitions apply, including in all aspects of the application, in all embodiments thereof.

[0022] All percentages are by weight of the composition (w / w) unless otherwise specified. "% wt." means weight percent. References to "parts" (e.g., a mixture of 1 part X and 3 parts Y) are ratios by weight. Unless specifically stated otherwise, all ratios or percentages are weight ratios or weight percentages.

[0023] "Active composition" is a composition free of water, and "active ingredient" is an ingredient free of water.

[0024] "QS" or "QSP" means a sufficient quantity for 100% or for 100 g. + / - indicates standard deviation. All ranges are inclusive and combinable. The number of significant digits in any numerical range indicates neither an intended nor a permissive limitation of claimed subject matter. All percentages refer to weight / weight unless otherwise indicated.

[0025] Unless otherwise indicated, all measurements are understood to be made at 25 °C and at ambient conditions, where "ambient conditions" means at a pressure of 1 atmosphere (atm) and at 65% relative humidity. "Relative humidity" means the ratio (expressed as a percentage) of the moisture content of air compared to the saturated moisture content at the same temperature and pressure. Relative humidity can be measured using a hygrometer, specifically a probe hygrometer available from VWR ® International.

[0026] "min" refers to "one minute" or "several minutes." "mol" refers to "moles" herein. "g" refers to "grams" herein following a number. "Ex." refers to "Example." All amounts related to the amounts of the listed ingredients are based on the content of the active material and do not include carriers or by-products that can be included in commercially available materials.

[0027] "comprise," "comprising," and "comprises" are intended to be non-limiting, in that they can be read to indicate that the named steps or components are included, but not to the exclusion of other steps or components.

[0028] As used herein, when used in a claim, the articles "a," "an," and "the" are understood to mean one or more of the specified entity.

[0029] As used herein, the terms "including," "comprising," and "containing" are intended to be non-limiting.

[0030] Where a given content range is given, this should be understood to mean the total amount of the recited ingredient in the composition, or where more than one species falls within the definition of an ingredient, the total amount of all ingredients in the composition meets the recited definition.

[0031] For example, if a composition contains 1% to 5% of a fatty alcohol, a composition containing 2% stearyl alcohol and 1% cetyl alcohol and no other fatty alcohol would fall within this range.

[0032] The amount of each particular ingredient or mixture thereof described below can constitute up to 100% (or 100%) of the total amount of ingredients in the composition.

[0033] As used herein, the term "free of" means that the composition contains 0% by weight of the composition of the ingredient, and thus no detectable amount of the ingredient.

[0034] As used herein, the term "substantially free of means less than about 1%, less than about 0.8%, less than about 0.5%, less than about 0.3%, or less than an insignificant amount, by weight of the composition.

[0035] "Comp. Ex." or "C. Ex." herein means "Comparative Example"; and "Ex." means "Example".

[0036] As used herein, the term "molecular weight" or "M.Wt." means weight average molecular weight, unless otherwise specified. Weight average molecular weight can be measured by gel permeation chromatography ("GPC").

[0037] As used herein, the term "personal cleansing composition" means a composition intended for topical application to the skin for cleansing.

[0038] As used herein, the term "mixture" means to include a simple combination of substances, as well as any compounds that can result from their combination.

[0039] The term "room temperature" means a temperature of 25°C.

[0040] As used herein, the term "rinse-off" means that the intended product use includes application to the skin, followed by rinsing and / or wiping the product from the skin within seconds to minutes of the application step. The product is typically applied and rinsed in the same use event, such as a shower or hand washing.

[0041] As used herein, the term "derivative" means a structure that is not shown but which one skilled in the art understands to be a modification of the base compound.

[0042] The term "apply" or "applying" as used in reference to a composition means to apply or spread the composition of the present application onto the skin.

[0043] The term "biodegradability test" as used herein refers to the test as described herein in the Test Methods section, wherein the test material is suspended in a phosphate buffered media containing an active sludge inoculum and the formation of carbon dioxide is measured via closed circuit respirometry. The test material is the sole source of carbon and energy and under aerobic conditions, the microorganisms metabolize the organic material producing CO2 as the end product.

[0044] The term "dermatologically acceptable" means that the composition or ingredient is suitable for use in contact with human skin tissue without undue toxicity, incompatibility, instability, allergic response, and the like.

[0045] The term "cosmetically acceptable" as used herein means that the composition, formulation or ingredient is suitable for use in contact with human keratinous tissue without undue toxicity, incompatibility, instability, allergic response, and the like. All compositions described herein intended to be administered directly to keratinous tissue are limited to those that are cosmetically acceptable.

[0046] Unless specifically noted, the methods as disclosed herein are cosmetic methods or non-therapeutic methods.

[0047] It is an object of the present application to provide new uses of personal cleansing compositions, methods of use of products, structures and corresponding compositions as described in the summary or as described hereinafter, to achieve the technical effects or objects set forth herein. These objects and other advantages that can be obtained by the present application will be apparent to those skilled in the art from the disclosure herein, in the summary and detailed description of the application, and in the claims that follow.

[0048] Beneficial effects

[0049] Salts of alkenyl sulfates with alkenyl chains as defined herein, especially but not limited to sodium oleyl sulfate, show superior antibacterial performance against Gram-positive bacteria, including Corynebacterium minutissimum (odor related) and Cutibacterium acnes (acne related); also against Gram-negative bacteria Escherichia coli in solution at pH up to or equal to 4.

[0050] A personal cleansing composition is provided for use in a method of inhibiting or killing the growth of bacteria on human skin, wherein the bacteria is selected from the group consisting of Escherichia coli, Cutibacterium acnes and Corynebacterium minutissimum in solution at pH up to or equal to 4; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate with an alkenyl chain, or an isomer thereof, or a mixture thereof, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms.

[0051] It has been found that the MIC results of sodium oleyl sulfate against Gram-positive bacteria are in the range of effective biocides such as benzalkonium chloride.

[0052] Thus, salts of alkenyl sulfates having an alkenyl chain comprising 18 to 20 carbon atoms; preferably 18 carbon atoms; such as sodium oleyl sulfate or personal cleansing compositions as set forth herein, or isomers thereof, or mixtures thereof, can be provided in methods of treating acne and eradicating C. acnes on human skin; preferably facial skin; or in methods of treating axillary malodor and killing C. diversus growing on human skin.

[0053] Surprisingly, some bactericidal activity of alkenyl sulfates having an alkenyl chain as defined herein, especially but not limited to sodium oleyl sulfate, on E. coli in solution can be observed when the pH is set to 4.

[0054] Salts of alkenyl sulfates having an alkenyl chain as defined herein, especially but not limited to sodium oleyl sulfate, are also compatible with commonly used surfactants such as sodium lauryl sulfate or sodium laureth sulfate (n) (hereinafter referred to as SLEnS) (where n is the average number of moles of ethoxylation, between 1 and 3; preferably 1 or 3) and / or betaines such as cocamidopropyl betaine and show good formulation feasibility in terms of foaming performance.

[0055] It has been found that salts of alkenyl sulfates having an alkenyl chain as defined herein, especially but not limited to sodium oleyl sulfate, are milder to the skin than sodium lauryl sulfate due to their unsaturated chain length.

[0056] Salts of alkenyl sulfates having an alkenyl chain as defined herein, especially but not limited to sodium oleyl sulfate (SOS), are considered to be "biodegradable" according to the biodegradability test method based on the OECD 301 B CO2release. This test method screens chemicals with rapid biodegradability in aerobic aqueous media (see the Examples section).

[0057] Therapeutic and non-therapeutic uses

[0058] All limitations and aspects as disclosed herein for the salts of personal cleansing compositions or alkenyl sulfates can apply to the following.

[0059] It has been found that the salts of alkenyl sulfates as set forth herein and thus the personal cleansing compositions can inhibit or kill specific bacteria, thereby providing a persistent protection against transient pathogenic microorganisms for humans.

[0060] As shown in more detail below, the salts of alkenyl sulfates as described herein have been subjected to minimum inhibitory concentration (MIC) tests and kill rate tests.

[0061] Salts of alkenyl sulfates having alkenyl chains as defined herein, especially but not limited to sodium oleyl sulfate, show superior antibacterial performance against gram positive bacteria including corynebacterium minutissimum (odor associated) and corynebacterium acnes (acne associated); also against gram negative bacteria escherichia coli at pH up to or equal to 4 in solution.

[0062] A personal cleansing composition is provided for use in a method of inhibiting or killing the growth of bacteria on human skin, wherein the bacteria is selected from the group consisting of escherichia coli, corynebacterium acnes, and corynebacterium minutissimum at pH up to or equal to 4 in solution; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain or an isomer thereof or a mixture thereof, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms.

[0063] Minimum inhibitory concentration results indicate that the salts of alkenyl sulfates or personal cleansing compositions as set forth herein can inhibit the growth of escherichia coli and other gram positive bacteria such as corynebacterium minutissimum and corynebacterium acnes at pH up to or equal to 4 in solution. The minimum inhibitory concentration results of the salts of alkenyl sulfates or personal cleansing compositions as set forth herein are in the range of effective biocides such as benzalkonium chloride.

[0064] Accordingly, a personal cleansing composition as set forth herein is provided for use in delivering an antimicrobial benefit on a topical surface of a human body. The topical surface of a human body can be a keratinous tissue surface. Keratinous tissue refers to the keratin-containing layer that is the outermost protective covering of a mammal, including but not limited to skin, hair, nails, or epidermis.

[0065] The topical surface of a human body can preferably be a human skin surface or a scalp surface.

[0066] It has also been found that the salts of alkenyl sulfates as set forth herein can exhibit a relatively strong bacterial inhibition effect against corynebacterium minutissimum and corynebacterium acnes.

[0067] Corynebacterium minutissimum is part of the corynebacterium genus, which is the primary pathogen of axillary malodor, with its primary malodor substrate believed to originate from apocrine glands. Accordingly, the salts of alkenyl sulfates and personal cleansing compositions as set forth herein can deliver an anti-malodor benefit.

[0068] Further, the salts of alkenyl sulfates as set forth herein can be provided for use in a method of eradicating corynebacterium acnes on human skin; preferably facial skin.

[0069] A personal cleansing composition as set forth herein is provided for use in a method of eradicating corynebacterium acnes on human skin; preferably facial skin.

[0070] C. acnes (formerly known as P. acnes) is associated with the skin acne condition. Thus, the salts of alkenyl sulfate esters as set forth herein can deliver anti-acne benefits.

[0071] It has been found that the salts of alkenyl sulfate esters as set forth herein do not exhibit an acceptable MIC against gram-negative bacteria such as E. coli. The MIC testing has been conducted at a pH of about 7.2.

[0072] However, the salts of alkenyl sulfate esters as set forth herein can kill the gram-negative bacteria E. coli in solution and at some acidic pH up to 4.

[0073] Thus, the salts of alkenyl sulfate esters as set forth herein can be provided for use in a method of killing E. coli growth in solution at a pH of at most or equal to 4.

[0074] The personal cleansing compositions as set forth herein are provided for use in a method of killing E. coli growth in solution at a pH of at most or equal to 4.

[0075] Non-therapeutic or cosmetic uses have also been discovered. The personal cleansing compositions as set forth herein are provided for non-therapeutic use in cleansing the skin; preferably in a gentle manner. The use of the personal cleansing compositions as set forth herein for gently cleansing the skin is compared to a control composition. The control composition comprises or consists of 10 wt.% sodium lauryl sulfate, 0.05 wt.% kathon CG (a combination of methylchloroisothiazolinone and methylisothiazolinone), sufficient citric acid to bring the pH to 5.5 ± 0.2 in sufficient water.

[0076] Mini-occluded corneometer moisture determination results as shown below demonstrate that the personal cleansing compositions as set forth herein comprising sodium oleyl sulfate as a salt of an alkenyl sulfate ester having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, are significantly gentler than a control composition comprising sodium lauryl sulfate.

[0077] The non-therapeutic use of the personal cleansing compositions as set forth herein is in their gentleness to the skin; preferably for preventing skin dryness.

[0078] The non-therapeutic use of the salt of an alkenyl sulfate ester having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms; or an isomer thereof; or a mixture thereof; preferably the sodium oleyl sulfate in a personal cleansing composition to increase the gentleness of the composition to the skin. By increasing the gentleness of the composition to the skin, it is intended to mean preventing skin tautness, skin roughness, and / or skin irritation.

[0079] As described above, a salt of an alkenyl sulfate having an alkenyl chain as set forth herein, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms; preferably, sodium oleyl sulfate can inhibit the Staphylococcus parum that causes axillary malodor.

[0080] Thus, a salt of an alkenyl sulfate having an alkenyl chain as set forth herein, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms; preferably, sodium oleyl sulfate as a non-therapeutic use as a deodorant on a product selected from the group consisting of: a consumer product, a household product, a cosmetic and personal care product, a product for use on the human body, a product applied to human skin, and a fragrance consumer product.

[0081] A salt of an alkenyl sulfate having an alkenyl chain as set forth herein, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms; preferably, sodium oleyl sulfate can be used as a deodorant in a personal cleansing composition for the axillary (underarm) skin surface.

[0082] Alternatively, a salt of an alkenyl sulfate having an alkenyl chain as set forth herein, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms; preferably, sodium oleyl sulfate can be used as a preservative in a personal cleansing composition.

[0083] In a personal cleansing composition, a salt of an alkenyl sulfate as used herein; preferably, sodium oleyl sulfate can be present in an amount ranging from about 0.01% to 5% by weight of the composition; preferably, in an amount ranging from about 0.02% to 3% by weight of the composition; more preferably, in an amount ranging from about 0.05% to 1.5% by weight of the composition; even more preferably, in an amount ranging from about 0.1% to 1% by weight of the composition; most preferably, in an amount ranging from about 0.2% to 0.5% by weight of the composition.

[0084] A personal cleansing composition as set forth herein for a non-therapeutic use for providing a cleansing benefit.

[0085] A personal cleansing composition as set forth herein for a non-therapeutic use for improving hand hygiene.

[0086] The personal cleansing composition, the salt of the alkenyl sulfate salt, and any form of the composition will be described in more detail hereinafter.

[0087] Personal cleansing compositions and forms

[0088] A personal cleansing composition is provided and comprises a salt of an alkenyl sulfate having an alkenyl chain or an isomer thereof or a mixture thereof, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms.

[0089] The salt of an alkenyl sulfate has the function of an antimicrobial active against specific bacteria as described herein. In addition, the salt of an alkenyl sulfate can have the function of an anionic surfactant.

[0090] The salt of an alkenyl sulfate as disclosed herein comprises a sulfate group (OSO3M) and has the following formula (I): (I) R is an alkenyl chain, and the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 atoms carbon. The alkenyl chain is directly connected to the oxygen of the sulfate group (OSO3M). Thus, the alkenyl chain R includes only carbon and hydrogen; and does not include any organic functional groups within the carbon backbone, such as hydroxyl groups, ether groups, esters, amides, or any amino groups.

[0091] The alkenyl chain R can comprise a straight alkenyl chain. The alkenyl chain R can have one or more double bonds.

[0092] Preferably, the alkenyl chain of the salt of an alkenyl sulfate can have 18 carbon atoms.

[0093] The salt of an alkenyl sulfate can be selected from the group consisting of alkali metals, ammonium, and alkanolamines. The alkali metal can be lithium, sodium, or potassium. The alkanolamine can be methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, or triethylamine.

[0094] Preferably, the salt of an alkenyl sulfate (M) can be selected from the group consisting of sodium, potassium, triethylamine, and ammonium.

[0095] More preferably, the salt of an alkenyl sulfate (M) can be selected from the group consisting of sodium and ammonium.

[0096] In particular, the salt of an alkenyl sulfate (M) is sodium.

[0097] The salt of an alkenyl sulfate having an alkenyl chain can be present in an amount ranging from about 0.01% to 50% by weight of the composition; preferably in an amount ranging from about 0.01% to 30% by weight of the composition; more preferably in an amount ranging from about 0.02% to 10% by weight of the composition; even more preferably in an amount ranging from about 0.05% to 5% by weight of the composition; most preferably in an amount ranging from about 0.1% to 1% by weight of the composition.

[0098] Alternatively, the salt of the alkenyl sulfate having an alkenyl chain may be present in an amount ranging from about 0.01% to 5% by weight of the composition; preferably in an amount ranging from about 0.02% to 3% by weight of the composition; more preferably in an amount ranging from about 0.05% to 1.5% by weight of the composition; even more preferably in an amount ranging from about 0.1% to 1% by weight of the composition; and most preferably in an amount ranging from about 0.2% to 0.5% by weight of the composition. This is, for example, when the composition is used as a hand sanitizer.

[0099] Salts of alkenyl sulfates having an alkenyl chain may be selected from the group consisting of: sodium oleyl sulfate, TEA-oleyl sulfate, ammonium oleyl sulfate, trans-oleyl sulfate, sodium phellandrene sulfate, sodium linoleyl sulfate, sodium linolenic acid sulfate, sodium cod alkenyl sulfate, or isomers thereof and mixtures thereof.

[0100] Salts of alkenyl sulfates can be prepared by sulfation of the corresponding unsaturated alcohols.

[0101] Typical examples of unsaturated alcohols whose sulfates can be used as antimicrobial active substances in personal care compositions include, in particular, oleyl alcohol (cis-9-octadecen-1-ol with an alkenyl chain of 18 carbon atoms), transoleyl alcohol (trans-9-octadecenol with an alkenyl chain of 18 carbon atoms), phellandrene alcohol (cis-6-octadecen-1-ol with an alkenyl chain of 18 carbon atoms), linoleyl alcohol (cis-,cis-9,12-octadecadien-1-ol with an alkenyl chain of 18 carbon atoms and two degrees of unsaturation), linolenic acid alcohol (cis-,cis-,cis-9,12,15-octadectrienol with an alkenyl chain of 18 carbon atoms and three degrees of unsaturation), or eicosenoenol (a type of alcohol with an alkenyl chain of 20 carbon atoms). Z )-Eicos-9-en-1-ol.

[0102] Preferably, the unsaturated alcohol whose sulfate can be used as an antimicrobial active substance in personal care compositions may particularly include oleyl alcohol (cis-9-octadecen-1-ol with an alkenyl chain of 18 carbon atoms) or eicosenoenol (an alkenyl chain of 20 carbon atoms) Z )-Eicos-9-en-1-ol.

[0103] More preferably, the unsaturated alcohols in which the sulfate can be used as antimicrobial active substances in personal care compositions may particularly include oleyl alcohol (cis-9-octadecen-1-ol with an alkenyl chain having 18 carbon atoms).

[0104] The unsaturated alcohol, whose sulfate salt can be used as an antimicrobial active, can comprise at least one double bond; preferably at the 9 position (between carbon 9 and carbon 10); more preferably comprise one single double bond at the 9 position. The unsaturated alcohol, whose sulfate salt can be used as an antimicrobial active, can include the cis isomer; preferably can include substantially the cis isomer.

[0105] Thus, it is preferred to use oleyl alcohol. The salt of an alkenyl sulfate can be selected from the group consisting of sodium oleyl sulfate, TEA-oleyl sulfate, ammonium oleyl sulfate, or isomers thereof, and mixtures thereof.

[0106] Preferably, the salt of an alkenyl sulfate can include sodium oleyl sulfate or ammonium oleyl sulfate. More preferably, the salt of an alkenyl sulfate can be sodium oleyl sulfate.

[0107] The sodium oleyl sulfate can be present in an amount ranging from about 0.01% to 50% by weight of the composition; preferably in an amount ranging from about 0.01% to 30% by weight of the composition; more preferably in an amount ranging from about 0.02% to 10% by weight of the composition; even more preferably in an amount ranging from about 0.05% to 5% by weight of the composition; most preferably in an amount ranging from about 0.1% to 1% by weight of the composition.

[0108] Alternatively, the sodium oleyl sulfate can be present in an amount ranging from about 0.01% to 5% by weight of the composition; preferably in an amount ranging from about 0.02% to 3% by weight of the composition; more preferably in an amount ranging from about 0.05% to 1.5% by weight of the composition; even more preferably in an amount ranging from about 0.1% to 1% by weight of the composition; most preferably in an amount ranging from about 0.2% to 0.5% by weight of the composition. This is the case, for example, when the composition is used as a hand sanitizer.

[0109] Typically, the salt of an alkenyl sulfate as described above can have a final active content of about 85% to about 99.9% by weight; preferably 85% to 90% by weight, as measured by the colorimetric two-phase (water / chloroform) mixed indicator (bromomethylphenylpyridinium / patent blue VF) titration method (ASTM International Standard Method D-3049-89 “Standard Test Method for Synthetic Anionic Ingredient by Cationic Titration”) using Hyamine 1622 as the cationic titrant.

[0110] The salt of an alkenyl sulfate as described above can comprise a mixture of cis and trans isomers.

[0111] Preferably, the salt of an alkenyl sulfate as described above can comprise the cis isomer; more preferably, wherein the salt of an alkenyl sulfate as described above comprises a mixture of the cis isomer and the trans isomer, wherein the weight ratio of the cis isomer to the trans isomer is about 8: 1 to about 99: 1 or about 8.5: 1 to about 95: 1 or about 8.5: 1 to about 9: 1. Most preferably, the salt of an alkenyl sulfate as described above can comprise substantially the cis isomer.

[0112] Preferably, the sodium oleyl sulfate can comprise the cis isomer; more preferably, wherein the sodium oleyl sulfate comprises a mixture of the cis isomer and the trans isomer, wherein the weight ratio of the cis isomer to the trans isomer is about 8: 1 to about 99: 1 or about 8.5: 1 to about 95: 1 or about 8.5: 1 to about 9: 1. Most preferably, the sodium oleyl sulfate can comprise substantially the cis isomer.

[0113] The salt of an alkenyl sulfate as described above can comprise at least one double bond; preferably at the 9 position (between carbon 9 and carbon 10); more preferably comprising one single double bond at the 9 position.

[0114] Preferably, the sodium oleyl sulfate can comprise one single double bond at the 9 position.

[0115] The personal cleansing composition can be in the form of a topical personal cleansing composition.

[0116] The topical personal cleansing composition can be selected from the group consisting of a shampoo, a cream, a lotion, a spray, a tonic, a gel, a paste, a mousse, a serum, an oil, a solid or liquid soap, a body wash, a hair conditioning composition, a hair moisturizing composition, a hair strengthening composition, a hair drying composition, a hair styling composition, a facial wash, a body wash, a skin moisturizing composition, a shaving preparation, a hand cleanser, a waterless hand sanitizer, a facial cleanser, a powder, a deodorant, an antidandruff hair care composition, and an antifungal hair care composition.

[0117] Another example of the personal cleansing composition can be a hand sanitizer. The hand sanitizer can generally be a leave-on product. The hand sanitizer can include, for example, an alcohol, an antibacterial active, a fragrance, a surfactant, a colorant, a bead, or any combination thereof. The alcohol for use herein can include, for example, ethanol, propanol, or a combination thereof. The alcohol can be present at a level of, for example, 30% to 80% by weight of the hand sanitizer composition.

[0118] The personal cleansing composition can be in the form of a solution, a dispersion, an emulsion, a foam, and other delivery mechanisms.

[0119] The personal cleansing composition herein can be a liquid personal cleansing composition. Preferably, the liquid personal cleansing composition can be selected from the group consisting of a liquid hand wash composition, a liquid body wash composition, a liquid hair wash composition, and combinations thereof. Preferably, the composition can be a liquid hand wash composition. One example of the composition herein can be a skin cleansing composition. The composition herein can be single phase or multi-phase.

[0120] The personal cleansing composition can be extruded or dispensed from a single chamber package. The personal cleansing composition can be in the form of a liquid, semi-liquid, cream, lotion, or gel or solid composition intended for topical application to the skin or hair.

[0121] Examples of the personal cleansing composition can include, but are not limited to, a shampoo, a conditioning shampoo, a hair conditioner, a body wash, a moisturizing body wash, a lathering body wash, a body wash gel, a body or bath cream, a skin cleanser, a cleansing milk, a hair and body cleanser, a body moisturizer, a gel, a lotion, an oil, a mousse, or a spray.

[0122] The product form contemplated for purposes of defining the personal cleansing composition and method is a rinse-off formulation, which means that the product is applied topically to the skin or hair and then subsequently (i.e., within a few minutes) washed off with water, or otherwise wiped off with a substrate or other suitable removal device.

[0123] A personal cleansing composition is provided and comprises a salt of an alkenyl sulfate as set forth herein and a dermatologically acceptable carrier for the personal cleansing composition.

[0124] The dermatologically acceptable carrier can be present at a level of from about 50% to about 99%, from about 60% to about 98%, from about 70% to about 98%, or alternatively from about 80% to about 95%, by weight of the composition.

[0125] The personal cleansing composition can comprise a dermatologically acceptable carrier. The dermatologically acceptable carrier is any carrier suitable for formulating the salt of an alkenyl sulfate into a personal cleansing composition suitable for application to the skin. The dermatologically acceptable carrier can be selected from an aqueous medium or an aqueous-alcohol medium. When the dermatologically acceptable carrier is an aqueous-alcohol carrier, the dermatologically acceptable carrier can comprise water and an alcohol. The alcohol can advantageously affect the viscosity of a relatively wide range of ingredients of the composition. The alcohol of the personal cleansing composition can be selected from the group consisting of ethanol, isopropyl alcohol, propanol, and mixtures thereof.

[0126] The inclusion of an appropriate amount of the dermatologically acceptable carrier can contribute to the formation of a personal cleansing composition having an appropriate liquid viscosity and rheology.

[0127] Alternatively, the dermatologically acceptable carrier can be water, or can be a miscible mixture of water and an organic solvent. Alternatively, the liquid carrier can be water having a minimal or no significant concentration of organic solvents, unless the organic solvent is otherwise incidentally incorporated into the composition as a trace ingredient in another essential or optional component. Suitable organic solvents can include aqueous solutions of lower alkyl alcohols and polyhydric alcohols. Useful lower alkyl alcohols include monohydric alcohols having from 1 to 6 carbon atoms, such as ethanol and isopropyl alcohol. Exemplary polyhydric alcohols include propylene glycol, hexylene glycol, glycerin, and propane diol.

[0128] Suitable organic solvents can include monohydric alcohols, dihydric alcohols, polyhydric alcohols, glycerin, glycols, polyalkylene glycols (such as polyethylene glycol), and mixtures thereof. Particularly suitable organic solvents can include lower aliphatic alcohols such as ethanol, propanol, butanol, isopropyl alcohol; glycols such as 1,2-propanediol, 1,3-propanediol, butylene glycol, pentylene glycol, hexylene glycol, heptylene glycol, octylene glycol, ethylhexylene glycol, decylene glycol; glycerin; water, and mixtures thereof. The composition can comprise, for example, water, a glycol, glycerin, or a combination thereof.

[0129] When the dermatologically acceptable carrier is an aqueous carrier, the aqueous carrier can consist essentially of water and can be substantially free of alcohol. The personal cleansing composition can comprise a safe and effective amount of a dermatologically acceptable carrier that is water. The personal cleansing composition can comprise from 0.1% to 99%, or from 1% to 98%, or from 10% to 97%, or from 30% to 95%, by total weight of the composition, of water.

[0130] The personal cleansing composition can be substantially free of alcohol, such as volatile alcohols (e.g., ethanol, isopropyl alcohol, propanol). When the personal cleansing composition is substantially free of alcohol, the personal cleansing composition can advantageously have reduced odor. Flammability issues can also be prevented.

[0131] The dermatologically acceptable carrier can be in a variety of forms. In some cases, the solubility or dispersibility of the salt of an alkenyl sulfonate or other components of the composition can dictate the form and characteristics of the carrier. Non-limiting examples include simple solutions (e.g., aqueous or anhydrous), dispersions, emulsions, and solid forms (e.g., gels, sticks, flowable solids, or amorphous materials).

[0132] In some cases, the dermatologically acceptable carrier can be in the form of an emulsion. The emulsion can have a continuous aqueous phase (e.g., oil-in-water or water-in-oil-in-water emulsion) or a continuous oil phase (e.g., water-in-oil or oil-in-water-in-oil emulsion). The oil phase can comprise silicone oil, non-silicone oil such as hydrocarbon oil, ester, ether, and mixtures thereof. The aqueous phase typically comprises water and water-soluble ingredients (e.g., humectants and / or other skin care actives). In some cases, the non-aqueous components of the composition include humectants, such as glycerin and / or other polyhydric alcohols.

[0133] In some cases, the compositions herein can be in the form of an oil-in-water ("O / W") emulsion, which provides a light and non-greasy sensory feel. Suitable O / W emulsions herein can include greater than 50% of a continuous aqueous phase by weight of the composition, and the remainder is a dispersed oil phase. The aqueous phase can include from 1% to 99% water, based on the weight of the aqueous phase, along with any water-soluble and / or water-miscible ingredients. In these cases, the dispersed oil phase will typically be present at less than 30% by weight of the composition (e.g., from 1% to 20%, from 2% to 15%, from 3% to 12%, from 4% to 10%, or even from 5% to 8%) to help avoid some of the undesirable sensory effects of an oily composition. The oil phase can include one or more volatile and / or non-volatile oils (e.g., plant oils, silicone oils, and / or hydrocarbon oils). Some non-limiting examples of oils that can be suitable for use in the compositions of the present application are disclosed in U.S. Patent No. 9,446,265 and U.S. Publication No. 2015 / 0196464.

[0134] The personal cleansing composition can further include sodium lauryl sulfate; preferably from about 0.5% to about 10% by weight of the composition of sodium lauryl sulfate; more preferably from about 1% to about 5% by weight of the composition of sodium lauryl sulfate; most preferably from about 2% to about 5% by weight of the composition of sodium lauryl sulfate. The addition of sodium lauryl sulfate to the composition helps to increase foam volume and foaming performance.

[0135] Optional ingredients

[0136] As can be appreciated, the cleansing compositions described herein can include a variety of optional components to adjust the properties and characteristics of the compositions. As can be appreciated, suitable optional components are well known and can generally include any component that is physically and chemically compatible with the essential components of the compositions described herein. The optional components should not otherwise unduly impair product stability, aesthetics, or performance. Further, the optional ingredients, when incorporated, should be suitable for use in contact with human skin tissue without undue toxicity, incompatibility, instability, allergic response, and the like.

[0137] The individual concentrations of the optional components can generally range from about 0.0001% to about 50%; from about 0.001% to about 20%; or even from about 0.01% to about 10% by weight of the composition. The optional components can be further limited to components that do not impair the transparency of the translucent composition.

[0138] Optional components can include, but are not limited to, conditioning agents (including hydrocarbon oils, fatty esters, silicones), cationic polymers, anti-dandruff actives and chelants. Additional suitable optional ingredients include, but are not limited to, encapsulated and unencapsulated perfumes or fragrances, colorants, particulates, foam boosters, anti-static agents, humectants, exfoliants, skin lightening agents, lubricants, propellants, self-foaming agents, pH adjusting agents and buffering agents, preservatives, pearlescent agents, opacifying agents, sensates, suspending agents, solvents, diluents, antioxidants, vitamins, minerals, peptides and peptide derivatives, sugar amines, sunscreens, oil control agents, and combinations thereof.

[0139] The CTFA Cosmetic Ingredient Handbook, Tenth Edition (published by the Cosmetic, Toiletry, and Fragrance Association, Inc. (Washington, D.C.) (2004) (hereinafter "CTFA") describes a wide variety of non-limiting materials that can be added to the compositions herein.

[0140] Method of use

[0141] A method of inhibiting the population of bacteria on an area in need of treatment is provided; preferably, wherein the bacteria are Corynebacterium parvum, Propionibacterium acnes, and / or Escherichia coli under certain conditions.

[0142] A method of inhibiting or killing the growth of bacteria on an area in need of treatment is provided; wherein the bacteria are Escherichia coli, Corynebacterium parvum, and / or Propionibacterium acnes at a pH up to or equal to 4, and comprising the step of topically applying an effective amount of a salt of an alkenyl sulfate as described herein to the area in need of treatment and optionally removing the composition after its application.

[0143] The salt of an alkenyl sulfate can have an alkenyl chain, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms, as described herein; preferably sodium oleyl sulfate, and optionally, removing the composition after its application.

[0144] A method of killing bacteria on the surface of skin; wherein the bacteria are Escherichia coli, Corynebacterium parvum, and / or Propionibacterium acnes at a pH up to or equal to 4, the method comprising the step of topically applying an effective amount of a personal cleansing composition as set forth herein to the area in need of treatment and optionally removing the composition after its application.

[0145] The area in need of treatment can be a keratinous tissue surface. Keratinous tissue refers to the keratin-containing layer that is the outermost protective covering of mammals, including but not limited to skin, hair, nails, or epidermis.

[0146] The area in need of treatment can preferably be a human skin surface or a scalp surface.

[0147] A method of controlling or eradicating C. acnes from a user's skin is provided and includes the step of applying a personal cleansing composition as set forth herein onto a desired skin surface of a user in need thereof; preferably onto a facial skin surface.

[0148] A personal cleansing composition as set forth herein can deliver anti-acne benefits. A method of controlling or eradicating C. acnes from the skin can be provided to reduce or eliminate acne on the skin.

[0149] A method of controlling or eradicating C. acnes from an axillary skin surface is provided and includes the step of applying a personal cleansing composition as set forth herein onto a desired skin surface of a user in need thereof; preferably onto an axillary skin surface.

[0150] A personal cleansing composition as set forth herein can deliver anti- malodor benefits. A method of controlling or eradicating C. acnes from an axillary skin surface can be provided to minimize malodors or unpleasant odors caused by the interaction of sebum, sweat, and C. acnes on an axillary skin surface.

[0151] A non-therapeutic method for cleansing skin is provided and includes the step of topically applying a personal cleansing composition as set forth herein onto an area in need of treatment, and optionally removing the composition after its application; preferably wherein the skin is gently cleansed.

[0152] The area in need of treatment can be a keratinous tissue surface. Keratinous tissue refers to the keratin-containing layer that is the outermost protective covering of mammals, including but not limited to skin, hair, nails, or epidermis.

[0153] The area in need of treatment can preferably be a human skin surface or a scalp surface.

[0154] A method of cleansing skin by washing the skin with a personal cleansing composition as set forth herein while avoiding the irritating effects of anionic surfactants to the skin, the anionic surfactant comprising or consisting of sodium lauryl sulfate.

[0155] A method of preserving a personal cleansing composition is provided and includes the steps of providing a personal cleansing composition and adding a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, as described herein; preferably sodium oleyl sulfate, to the personal cleansing composition.

[0156] In this method, the salt of an alkenyl sulfate; preferably, sodium oleyl sulfate can be present in an amount ranging from about 0.01% to 5% by weight of the composition; preferably in an amount ranging from about 0.02% to 3% by weight of the composition; more preferably in an amount ranging from about 0.05% to 1.5% by weight of the composition; even more preferably in an amount ranging from about 0.1% to 1% by weight of the composition; most preferably in an amount ranging from about 0.2% to 0.5% by weight of the composition.

[0157] Test methods

[0158] It is understood that the test methods disclosed in the Test Methods section of the application apply for determining the respective parameter values of this application as described by the Applicant's invention and as claimed.

[0159] Minimum inhibitory concentration (MIC)

[0160] In vitro minimum inhibitory concentration (MIC) test

[0161] In vitro minimum inhibitory concentration (MIC) assays are techniques used to determine the lowest concentration of a particular compound required to prevent the growth of a microorganism. Different microorganisms were used to assess the bacterial inhibitory benefit of the sulfate surfactant (Table 1)

[0162] Table 1

[0163] Microorganisms were cultured and maintained in different media. Each respective microorganism stock solution was diluted to 10 5 to 10 6 CFU / mL in the respective growth medium. 180 ml of broth containing the respective target microorganism was dispensed into a 96-well plate.

[0164] For example, Micrococcus paucivorans ATCC 23348 was cultured on Tryptic Soy Agar (TSA) (Oxoid CM0131) for 24 hours. Single colonies were then transferred to 20 mL of Tryptic Soy Broth (Oxoid CM0129B - TSB) and incubated at 37°C at 200 rpm / min overnight. Bacterial cells in broth were diluted to 10 5 to 10 6 CFU / mL in TSB. 180 μL of this bacteria-MHB mixture was added to a 96-well flat bottom plate (Nunc ™ MicroWell ™ 96-well, Cat. No. 167008).

[0165] Oil-based sodium sulfates prepared from two different synthesis batches (Ex. 1A and Ex. 1B), octyl sodium sulfate, decyl sodium sulfate, lauryl sodium sulfate were mixed with deionized (DI) water, respectively. Stearyl sodium sulfate was mixed in dimethyl sulfoxide (DMSO).

[0166] Two-fold serial dilutions were performed for each respective active by mixing 100 ml of the active stock solution (starting from 1 wt%) with 100 ml of sterile DI water or DMSO and placed in 96-well plates (Nunc ™ MicroWell ™ 96-well, Cat. No. 167008). For each assay, a treatment solution was prepared from 0.001 wt% to 1 wt% for each individual active.

[0167] Using a micropipette, 20 ml of the active at different concentrations was transferred to each well with 180 ml of broth containing the respective target microorganism.

[0168] The 96-well plates with the test microorganism and the test active were incubated at 37°C.

[0169] a) E. coli was incubated overnight for 16 to 24 hours.

[0170] b) C. parvum was incubated for two days.

[0171] c) C. acnes was incubated for two days under anaerobic conditions.

[0172] After incubation, the microbial growth in the presence of the test active was determined by visual inspection or spectrophotometer by OD600 (absorbance at 600 nm using a Tecan M200 Infinite Pro microplate reader) reading compared to the positive control (broth with the individual microorganism) and the negative control (broth only). The MIC value is expressed as parts per million (ppm) of the different actives.

[0173] Kill rate testing in liquid test method

[0174] Suspension time-kill testing

[0175] Suspension time-kill test is a method to directly sterilize a liquid test article with a high concentration of test microorganism and then determine the percentage of kill (usually expressed as log CFU reduction) over time. The purpose is to measure the biocidal potential of a liquid antimicrobial active or formulation.

[0176] KRT test procedure : E. coli ATCC 25922 was streaked on Tryptic Soy Agar (TSA) plates and incubated overnight. One colony of E. coli ATCC 25922 was picked and the bacterial cells were subcultured in Tryptic Soy Broth (TSB) at 200 rpm / min at 37°C for 12 to 16 hours.

[0177] After incubation, 1 mL of bacterial cells from the broth was pipetted into a 2 mL tube. The sample was centrifuged at 13000 rpm / min for 2 min. The cell supernatant was discarded and the bacterial cells were resuspended in 1 mL of physiological saline at a concentration of 10 8 to 10 9 CFU / mL.

[0178] 1 mL of different concentrations of the liquid antimicrobial active to be tested was prepared: The pH of the test solution was maintained between 4.0 and 5.7 using 20 mM acetate buffer.

[0179] The pH of the test solution was maintained around 7.2 using 10 mM phosphate buffer.

[0180] The pH of the test solution was maintained between 8.0 and 9.0 using 20 mM Tris-HCl buffer.

[0181] 1 mL of physiological saline (NaCI 0.9% by weight) was used as a negative control in this study.

[0182] 50 ml of 10 8 to 10 9 CFU / mL of bacterial cells were added to each treatment and physiological saline control. The samples were mixed well by vertex mixing for 5 seconds.

[0183] After 30 minutes of incubation, 50 ml of liquid from each treatment sample and physiological saline control was pipetted out into a Total Viable Count vial (NEOGEN). All measurements were performed in duplicate.

[0184] The detection time (DT) of the Total Viable Count vials was measured by the Soleris ® Next Generation (NEOGEN) system. The DT values of each treatment and control were averaged for further calculations.

[0185] The DT time of each sample was converted to Log (number of viable cells) by using the algorithm generated for E. coli ATCC 25922: Log CFU of each sample = a DT + b (a, slope; b, intercept) The biocidal potential of different active substances at different concentrations and different pH in liquid solutions was measured by the following method: Log CFU reduction = Log CFU (saline control) - Log CFU (treatment) Graduated cylinder method Foam can be measured according to the graduated cylinder method. A graduated cylinder and a rotating mechanical device are used to measure the foam volume. A 1,000 mL graduated cylinder is used that is marked in 10 mL increments, has a height of 14.5 inches from the inside of its bottom to the 1,000 mL mark, and has a neck that fits an inset plastic lid (e.g., Pyrex No. 2982) at its top. A moderately hard water (about 7 gpg or about 120 ppm) is prepared by dissolving 1.14 grams of calcium chloride dihydrate and 1.73 grams of magnesium chloride hexahydrate in one US gallon of distilled water. The water is maintained at a temperature of between 40.5 °C to 43.3 °C (105 to 110 between about 20°C and about 25°C. The graduated cylinder is heated to about the same temperature by rinsing with an excess of tap water of the same temperature for about 15 seconds, then drying the outside and shaking up and down briefly to dry the inside. 100.0 grams of the desired temperature of moderately hard water is weighed directly into the graduated cylinder. The cylinder is clamped in a mechanical rotary device that clamps the cylinder vertically at a position where its rotational axis is transverse through the center of the graduated cylinder. Using a 3 or 4 place balance, invert the plastic cap for the graduated cylinder on the balance pan and hold the cap level using a clamp, weigh 0.500 grams of composition that comprises less than 19% surfactant (weigh 0.250 grams of composition that comprises greater than or equal to 19% surfactant) to an accuracy of within 4 milligrams. Insert the cap into the neck of the cylinder, being careful that all of the composition is now in the space inside the cylinder. For compositions that have very low viscosity that do not stay on the surface of the cap, 500 mg of composition can be added directly to the graduated cylinder. Rotate the cylinder for 25 complete rotations at a rate of about 10 rotations per 18 seconds to create a foam and stop at the vertical position in the horizontal state. When the cylinder is stopped in the vertical position, start a digital stopwatch. Observe the drainage at the bottom and when the water height measures 50 cc, then 60 cc, then 70 cc, etc. until at least 90 cc has drained, record the time to the second. Measure and record the total height of the foam inside the column, which is the foam volume. If the top surface of the foam is not flat, take the lowest height in the middle of the cross section of the graduated cylinder that can be seen as the foam volume (mL) if the foam is coarse such that a single or only a few foam units ("bubbles") span the entire cylinder, then take the height at which at least about 10 foam units fill the space as the foam volume, again in mL from the bottom up. When measuring the foam height, bubbles that are greater than about 25.4 mm (1 inch) across the top surface are considered free air and not foam. Repeat the measurement and average the results of at least three to obtain the foam volume. In a spreadsheet, calculate the foam density at each observation time point as the foam volume (total height minus water height) divided by the foam weight (100.5 grams minus the observed water weight, using a water density of 1.00 g / cc). Fit a second order polynomial equation to the 3 time points closest to (ideally, also including) 20 seconds. Solve the equation for the foam density at 20 seconds, which is the foam density of the composition. Multiply the foam volume by the foam density to obtain the foam mass in grams.

[0186] The entire measurement process should take less than about 3 minutes in order to maintain the desired temperature.

[0187] Mini- immersion method protocol

[0188] This was a two-day, randomized, blinded (subject and instrument operator), forearm microdip panel study designed to evaluate the irritant potential of various cleanser solutions versus a water only control. All subjects (n=16) completed the informed consent, screening, and enrollment procedures and then the eligible subjects were scheduled for a treatment visit. During the treatment visit, subjects acclimated for 20 minutes in a temperature and humidity controlled environment (21 + / - 1 °C, 70 + / - 2 and 30% to 45% relative humidity). During acclimation, the treatment site was marked on the volar surface of one forearm of the subject. On the second day, the other forearm was used and marked accordingly. After acclimation was complete, a baseline corneometer measurement was obtained to record hydration of the stratum corneum via capacitance.

[0189] Once the baseline corneometer measurement was complete, the subjects had open glass microdip cups strapped to the forearms using an elastic band. Then, according to the study randomization, the prepared solutions (test product diluted 10% in DI water and heated to 44 °C) were pipetted into each respective cup. Once all products were assigned to the cups, a 15 minute timer was started. Once the 15 minute exposure time had elapsed, the solutions were pipetted from the cups into a waste container and the cups were removed from each arm. The forearms were briefly rinsed under a running faucet (temperature between 35 °C to 37.8 °C; 95 to 100 ) and gently patted dry. The subjects were allowed to rest for 10 minutes and then acclimated again for 30 minutes in the temperature and humidity controlled environment prior to a post-treatment corneometer measurement. Once the post-treatment measurement was complete, the entire procedure was repeated until three 15 minute exposures had elapsed, each followed by a 10 minute subject rest, 30 minute acclimation, and 40 minute post-treatment evaluation. During the 15 minute exposure period, the subjects were asked to sit quietly with the forearms facing upwards, comfortably resting on the arms of a chair or table surface to prevent leakage and / or splashing of the solutions within the cups.

[0190] NMR content method

[0191] NMR content method for determining the molar and weight percent based ratios of cis / trans isomers of oil-based sodium sulfates having different NMR signals.

[0192] In this method, proton NMR spectroscopy is used to analyze samples of soluble material in an organic solvent and the different 1 H-NMR domains are peak integrated and compared to an internal standard to determine the ratio of protons and carbons of the isomers.

[0193] A flowable solution of less than 10 wt% of the sample is dissolved in a stock solution of 5 wt% internal standard in organic solvent. The solution is transferred to a 5 mm NMR glass vial and placed in the sample holder (well) of the NMR instrument. Data is acquired using a Bruker NMR instrument with a 600 MHZ field strength, equipped with a cryo-Prodigy probe using a quantitative proton sequence. The appropriate parameters used are as follows: acquisition time (FID length) of 2.7 s, relaxation time of 60 s, 90 degree pulse width, spectral width of 20 ppm, 32k points in the FID and using 8 repeated scans. In the Fourier transform step, an exponential weighting with 0.3 Hz line broadening is used and the spectrum is phased to absorption. A baseline correction is used to ensure a flat baseline on either side of the peaks to be integrated.

[0194] The following peak regions are typically used for quantitation and are integrated with the internal standard: 1) Olefinic CH region for cis isomer at 5.37 ppm - 5.32 ppm 2) Olefinic CH region for trans isomer at 5.40 ppm - 5.38 ppm Molar ratio and weight percent calculations are as follows: Cis / trans molar ratio = (cis region integral) / (cis region integral) Component wt% = ( (mass of internal standard in sample) / (molecular weight of internal standard) ) ( (cis or trans region integral) / (internal standard region integral) ) (molecular weight of oleyl sulfate) (1 / (mass of oleyl sulfate material in sample) ) 100 Biodegradation test method Biodegradability of the salt of an olefinic sulfonate, preferably sodium oleyl sulfate, can be tested according to the following method. The biodegradability test method is based on the Organization for Economic Cooperation and Development (OECD) 301B CO2 Release Biodegradation Test Method, which screens chemicals for rapid biodegradability in an aerobic aqueous medium.

[0195] In this test, the test substance is suspended in a phosphate buffer nutrient salt medium containing an inoculum of activated sludge and the formation of carbon dioxide is measured via closed circuit respirometry. The test substance is the sole source of carbon and energy and under aerobic conditions, the microorganisms metabolize the organic material producing CO2 as the end product. A known amount of carbon is added to the test system and biodegradation is calculated as a percentage of theoretical CO2 formation. The test is typically run for 28 days.

[0196] Rapid biodegradability is the definition of regulatory agencies for classification of materials that meet the pass level described in the OECD 301 B guideline. Specifically, biodegradation to the following pass level of 60% theoretical carbon dioxide (ThCO2) obtained within 28 days can be considered as evidence of rapid biodegradability. The pass level must be reached within a 10-day window of the 28-day test period. The 10-day window starts when the degree of biodegradation reaches 10% ThCO2 and ends 10 days later or on the 28th day of the test, whichever comes first.

[0197] Examples

[0198] The following examples further describe and demonstrate embodiments within the scope of the present application. These examples are given to illustrate the application and cannot be considered as limiting the application as there can be numerous variations and modifications of the application which fall within the ambit of the application. The ingredients used herein are identified by chemical or INCI name, unless otherwise defined herein below.

[0199] Example 1 : Method of making sodium oleyl sulfate

[0200] Sodium oleyl sulfate was prepared from oleyl alcohol and sulfur trioxide pyridine complex according to the following method: To a 1 -liter 3 -necked round bottom reaction flask equipped with a magnetic stir bar was added 104.7 grams (0.3845 moles) of technical grade oleyl alcohol (Alfa Aesar product number A18018), 350 mL of dichloromethane (EMD Millipore product number DX0835), and 2 mL of pyridine (Sigma Aldrich product number 270970). A water cooled condenser was attached to one side neck of the reaction flask, and dry nitrogen feed was introduced from a gas bubbler at the top of the condenser. With mixing at room temperature (21 °C) under a nitrogen atmosphere, 65.6 grams (0.404 moles) of 98% sulfur trioxide pyridine complex (Sigma Aldrich product number S7556) was added. A stopper was then fitted to the center neck of the reaction flask, and a thermometer was fitted to the other side neck. With mixing under a nitrogen atmosphere, the reaction mixture was heated at gentle reflux overnight using a heating mantle (temperature reading of 39-40 °C). The reaction mixture was then allowed to cool to room temperature, followed by gravity filtration through Whatman 4 grade filter paper to remove any residual solids. The filtered reaction mixture was concentrated by evaporation of the dichloromethane using a rotary evaporator. To the concentrated reaction product was added 87.4 grams (0.398 moles) of 24.6 wt% sodium methoxide in methanol (Sigma Aldrich product number 156256) and 750 mL of methanol (EMD Millipore product number MX0475P), and mixed until all solids were dissolved. A small sample was taken and dissolved in DI water, and the pH was measured to be 10-11 using pH test strips. Additional sodium methoxide can be added if needed to reach a pH of 10-11. The mixture was concentrated by evaporation of the methanol and pyridine using a rotary evaporator. To the concentrated product was added 450 mL of deionized water (18.2 megohm-cm filtered water from a Millipore water filtration unit), 450 mL of absolute ethanol (EMD Millipore product number EX0276), and mixed until all solids were dissolved. The solution was transferred to a 2-liter separatory funnel along with 500 mL of hexanes (EMD Millipore product number HX0299). The contents of the separatory funnel were shaken thoroughly and allowed to separate overnight. The next day, the lower aqueous layer was drained and concentrated by placing in a vacuum oven under reduced pressure to evaporate the solvent. The product was occasionally removed from the vacuum oven and mixed, broken up, and eventually ground into smaller pieces before being placed back into the vacuum oven to facilitate solvent removal. Once the product was no longer losing significant mass, the vacuum oven drying was stopped, and the product was transferred to a jar and stored sealed.

[0201] The final active matter content of the oleyl sodium sulfate product was determined to be 86.6 wt% by using the accepted colorimetric two-phase (water / chloroform) mixed indicator (Xanthydrol (Sigma Aldrich product number 41785) / Patent Blue VF (Sigma Aldrich product number 76357)) titration method (ASTM International Standard Method D-3049-89 “Standard Test Method for Synthetic Anionic Ingredient by Cationic Titration”) with Hyamine 1622 (Sigma Aldrich product number 51126) as the cationic titrant.

[0202] From Example 1, two different synthesis batches (Ex. 1A, Ex. 1B) were prepared: Ex. 1A (white powder) contained a mixture of 51 wt% of the cis isomer and 6 wt% of the trans isomer. Thus, the oleyl sodium sulfate contained the cis isomer. The oleyl sodium sulfate contained a mixture of the cis isomer and the trans isomer, wherein the weight ratio of the cis isomer to the trans isomer was 8.5:1.

[0203] Ex. 1B (tawny powder) contained a mixture of 72 wt% of the cis isomer and 8 wt% of the trans isomer. Thus, the oleyl sodium sulfate contained the cis isomer. The oleyl sodium sulfate contained a mixture of the cis isomer and the trans isomer, wherein the weight ratio of the cis isomer to the trans isomer was 9:1.

[0204] Biodegradability results

[0205] The oleyl sodium sulfate theoretical carbon dioxide % (ThCO2) was 83.46% over 28 days and met the 10-day window requirement, thus meeting both requirements for rapid biodegradability.

[0206] Minimum inhibitory concentration determination

[0207] Table 2 shows the minimum inhibitory concentrations of different anionic sulfate surfactants against known bacteria such as Staphylococcus aureus (for comparison), Escherichia coli, bacteria associated with body odor such as Corynebacterium parvum, bacteria associated with acne such as Cutibacterium acnes. Two different batches of oleyl sodium sulfate (Ex. 1A, Ex. 1B) have been tested.

[0208] Table 2. MIC data for sodium oleyl sulfate and other sulfate salts NA: not tested Staphylococcus aureus is a relevant comparative pathogen target for inhibition. The results in Table 2 demonstrate that oleyl sodium sulfate is a known effective antimicrobial agent for inhibiting Staphylococcus aureus. This is in contrast to octadecyl sodium sulfate which differs from oleyl sodium sulfate in that there is no unsaturation (double bonds within the carbon backbone). Octadecyl sodium sulfate is not effective against Staphylococcus aureus. No inhibition was observed for octyl sodium sulfate and decyl sodium sulfate. Lauryl sodium sulfate, which has only 12 carbon atoms, showed an MIC against Staphylococcus aureus, however lauryl sodium sulfate is not as effective as oleyl sodium sulfate.

[0209] The MIC results for oleyl sodium sulfate against Gram-positive bacteria such as Staphylococcus aureus are in the range of effective biocides such as benzalkonium chloride.

[0210] However, at the assay pH of 7.2, oleyl sodium sulfate is not effective against the Gram-negative bacterium Escherichia coli.

[0211] Now, oleyl sodium sulfate also exhibits strong bacterial inhibition against Corynebacterium parvum and C. acnes (two strains).

[0212] Corynebacterium is the primary pathogen of axillary odor, and its primary malodor substrate is believed to originate from the apocrine gland.

[0213] Thus, it is possible to provide a personal cleansing composition for use in a method of treating axillary malodor and killing Corynebacterium parvum growing on human skin; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof.

[0214] C. acnes SK137 and C. acnes 2044 NIA (P&G skin isolate) are from the IA-2 clade by whole genome sequencing and are reported to be associated with the skin acne condition. Moreover, the data of Table 2 suggest that oleyl sodium sulfate has the potential to deliver anti-malodor and anti-acne benefits.

[0215] Notably, no existing data has been found to show that oleyl sodium sulfate can be used in a method of inhibiting or killing C. acnes growth. In particular, Table 2 shows that oleyl sodium sulfate has a greater antibacterial efficacy than saturated octadecyl sodium sulfate for inhibiting or killing C. acnes growth. In fact, octadecyl sodium sulfate has no effect on inhibiting or killing C. acnes growth.

[0216] In other words, by selecting an unsaturated alkyl chain or alkenyl chain (wherein the alkenyl chain comprises 18 to 20 carbon atoms; preferably 18 carbon atoms), the resulting personal cleansing composition can treat acne is unexpected.

[0217] Thus, it can be provided a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms; preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof, such as sodium oleyl sulfate, or a personal cleansing composition as set forth herein, for use in a method of inhibiting or killing the growth of bacteria on human skin; wherein the bacteria is Micrococcus minimus or Cutibacterium acnes.

[0218] It can be provided a personal cleansing composition for use in a method of treating acne and eradicating Cutibacterium acnes on human skin; preferably facial skin; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof.

[0219] Kill rate testing in liquid

[0220] Previous MIC data for sodium oleyl sulfate was ineffective against gram-negative E. coli at a measured pH of 7.2. However, when the pH was set to be up to or equal to 4, some bactericidal activity of sodium oleyl sulfate against E. coli in solution could be observed (Table 3).

[0221] Table 3. Germicidal activity of sodium oleyl sulfate against Escherichia coli ATCC 25922

[0222] Thus, it appears that a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms; preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof, such as sodium oleyl sulfate, can however have bactericidal activity against gram-negative bacteria such as E. coli under conditions where the pH in solution is up to or equal to 4.

[0223] Thus, it can be provided a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms; preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof, such as sodium oleyl sulfate, or a personal cleansing composition as set forth herein, for use in a method of killing E. coli under conditions where the pH in solution is up to or equal to 4.

[0224] Personal cleansing compositions

[0225] The following examples were prepared: Composition (wt%)

[0226] Component definitions 1 Sodium oleyl sulfate; P&G 2 Sodium lauryl sulfate; Guangzhou Litze Chemical Co., Ltd. 3 Cocamidopropyl betaine; Guangzhou Tinci Materials Technology Co., Ltd. 4 Sodium chloride; Sigma 5 Kathon CG, Dupont 6 Citric acid powder; Yixing Union Biochemical q.s.: sufficient quantity Foam benefit Some personal cleansing compositions can perform poorly in terms of lathering and thus cleansing, which are features of interest to consumers. Personal cleansing compositions as set forth herein comprising salts of alkenyl sulfate esters having alkenyl chains comprising 18 to 20 carbon atoms, such as sodium oleyl sulfate, can also have consumer-acceptable lathering properties, as shown above.

[0227] Foam can be measured according to the cylinder method described herein. The composition can have a foam volume of about 450 mL or more; preferably about 480 mL or more; more preferably from about 480 mL to about 1050 mL. The composition can have a foam density of about 0.03 g / cc, about 0.04 g / cc, about 0.05 g / cc, 0.055 g / cc, 0.06 g / cc, 0.065 g / cc or more. The composition can have a foam mass of about 20 g, about 25 g, about 30 g, about 35 g, about 40 g, about 45 g or more.

[0228] Accordingly, Ex. B and Ex. C have acceptable lathering properties in terms of foam volume. Notably, Ex. B comprising a mixture of sodium oleyl sulfate and sodium lauryl sulfate shows increased foam volume.

[0229] Mini- immersion corneometer results

[0230] The following examples were prepared and evaluated in terms of mildness: Composition (wt%) Corneometer results at baseline before treatment Stratum corneum moisture meter results after one treatment (higher is better) Stratum corneum moisture meter results after two treatments (higher is better) Stratum corneum moisture meter results after three treatments (higher is better)

[0231] The results show that the personal cleansing compositions comprising sodium oleyl sulfate are significantly milder than the personal cleansing compositions comprising sodium lauryl sulfate based on the higher stratum corneum moisture meter results for Ex. E vs. C. Ex. D after one, two, and three treatments.

[0232] Thus, the personal cleansing compositions as set forth herein can be used to gently cleanse the skin; as compared to a control composition comprising 10% sodium lauryl sulfate by weight of the control composition, 0.05% kathon CG by weight of the control composition, a sufficient amount of citric acid to achieve a pH of 5.5 ± 0.2 in a sufficient amount of water.

[0233] Additional examples / combinations

[0234] A. A salt of an alkenyl sulfate having an alkenyl chain comprising from 18 to 20 carbon atoms; preferably wherein the salt of the alkenyl sulfate having the alkenyl chain comprises a sulfate group and has the following formula (I): (I) wherein R is an alkenyl chain, and the alkenyl chain comprises from 18 to 20 carbon atoms, and wherein the salt of the alkenyl sulfate (M) is selected from the group consisting of an alkali metal, ammonium, and an alkanolamine; more preferably sodium oleyl sulfate, for use in a method of inhibiting or killing the growth of bacteria on human skin, wherein the bacteria is selected from the group consisting of E. coli, S. epidermidis, and C. minimissimum at a pH up to or equal to 4 in solution.

[0235] B. A salt of an alkenyl sulfate having an alkenyl chain comprising from 18 to 20 carbon atoms; preferably sodium oleyl sulfate, for use in a method of eradicating S. epidermidis on human skin; more preferably on facial skin.

[0236] C. A salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms; preferably sodium oleyl sulfate, or an isomer thereof, or a mixture thereof, for use in a method of treating axillary malodor and killing bacteria growing on human skin; wherein the bacteria is Corynebacterium minutissimum.

[0237] D. A personal cleansing composition comprising a salt of an alkenyl sulfate as set forth herein, for use in a method of inhibiting or killing bacteria growing on human skin, wherein the bacteria is selected from the group consisting of Escherichia coli, Staphylococcus hominis, and Corynebacterium minutissimum at a pH up to or equal to 4 in solution.

[0238] E. A personal cleansing composition for use in a method of treating acne and eradicating Staphylococcus hominis on human skin; preferably facial skin; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof.

[0239] F. A personal cleansing composition for use in a method of treating axillary malodor and killing bacteria growing on human skin; wherein the bacteria is Corynebacterium minutissimum, wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof.

[0240] G. A salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms; preferably sodium oleyl sulfate, as set forth herein, for a non-therapeutic use as a deodorant on a product selected from the group consisting of a consumer product, a household product, a cosmetic and personal care product, a product for use on the human body, a product applied to human skin, and a fragrance consumer product.

[0241] H. The non-therapeutic use according to paragraph G, wherein the salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms; preferably sodium oleyl sulfate, as set forth herein, is used as a deodorant in a personal cleansing composition for axillary skin surfaces.

[0242] I. A personal cleansing composition as set forth herein for a non-therapeutic use to provide a cleansing benefit.

[0243] J. A personal cleansing composition as set forth herein for a non-therapeutic use to improve hand hygiene.

[0244] K. A non-therapeutic use of a personal cleansing composition as set forth herein is its mildness to the skin; preferably for preventing skin dryness.

[0245] L. A salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms; preferably sodium oleyl sulfate; or an isomer thereof; or a mixture thereof; for use in a personal cleansing or personal cleansing composition to increase the mildness of the composition to the skin; more preferably for non-therapeutic use by preventing skin tautness, skin roughness and / or skin irritation.

[0246] M. A personal cleansing composition for use in gently cleansing the skin; preferably compared to a control composition comprising 10% sodium lauryl sulfate, 0.05% kathon CG, sufficient citric acid to give a pH of 5.5 ± 0.2 in an adequate amount of water; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms; or an isomer thereof; or a mixture thereof.

[0247] N. A personal cleansing composition for use in preventing skin dryness; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms; or an isomer thereof; or a mixture thereof.

[0248] O. A method of inhibiting or killing the growth of bacteria on an area in need of treatment; wherein the bacteria are E. coli, M. gryphicium and / or S. hominis at a pH up to or equal to 4, the method comprising the steps of topically applying an effective amount of a salt of an alkenyl sulfate as described herein to the area in need of treatment and optionally removing the composition after its application.

[0249] P. A method of killing bacteria on the surface of the skin; wherein the bacteria are E. coli, M. gryphicium and / or S. hominis at a pH up to or equal to 4, the method comprising the steps of topically applying an effective amount of a personal cleansing composition as set forth herein to the area in need of treatment and optionally removing the composition after its application.

[0250] Q. A method of controlling or eradicating S. hominis from the skin of a user, the method comprising the step of applying an effective amount of a personal cleansing composition as set forth herein to the desired skin surface of a user in need thereof; preferably to the facial skin surface.

[0251] R. The method according to paragraph Q for use in reducing or eliminating acne on the skin.

[0252] S. A method of controlling or eradicating M. gryphicium from the axillary skin surface, the method comprising the step of applying an effective amount of a personal cleansing composition as set forth herein to the desired axillary skin surface of a user in need thereof; preferably to the axillary skin surface.

[0253] T. The method according to paragraph S for minimizing malodour or unpleasant odour caused by the interaction of sebum, sweat and Micrococcus minimus on the surface of axillary skin.

[0254] U. A non-therapeutic method for cleansing the skin, wherein the method comprises the step of topically applying a personal cleansing composition as set forth herein onto an area in need of treatment, and optionally removing the composition after its application; preferably wherein the skin is gently cleansed.

[0255] V. A method of cleansing the skin by washing the skin with a personal cleansing composition as set forth herein while avoiding the irritating effect of anionic surfactants consisting of sodium lauryl sulfate on the skin.

[0256] W. Use of a personal cleansing composition comprising a salt of an alkenyl sulfate as set forth herein for the manufacture of a medicament for inhibiting or killing the growth of bacteria on human skin, wherein the bacteria is selected from the group consisting of Escherichia coli, Cutibacterium acnes and Micrococcus minimus at pH up to or equal to 4 in solution.

[0257] X. Use of a personal cleansing composition for the manufacture of a medicament for treating acne and eradicating Cutibacterium acnes on human skin; preferably facial skin; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof or a mixture thereof.

[0258] Y. Use of a personal cleansing composition for the manufacture of a medicament for treating axillary malodour and killing the growth of bacteria on human skin; wherein the bacteria is Micrococcus minimus, wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain comprising 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof or a mixture thereof.

[0259] The dimensions and values disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise specified, each such dimension is intended to mean both the exact value and a functional equivalent range surrounding that value. For example, a dimension disclosed as "40 mm" is intended to mean "about 40 mm."

[0260] Every document cited herein, including any cross referenced or related patent or application, is hereby incorporated by reference in its entirety unless expressly excluded or otherwise limited. The citation of any document is not an admission that it is prior art with respect to any application disclosed or claimed herein or that it alone, or along with any other document or matter, teaches, suggests or discloses any such application. Further, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to that term in this document shall govern.

[0261] While particular embodiments of the present application have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the application. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this application.

Claims

1. A personal cleansing composition for use in a method of inhibiting or killing the growth of bacteria on human skin, wherein the bacteria is selected from the group consisting of E. coli, S. hominis and C. minutissimum at pH up to or equal to 4 in solution; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate ester having an alkenyl chain, or an isomer thereof, or a mixture thereof, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms.

2. A personal cleansing composition for use in a method of treating acne and eradicating S. hominis on human skin; preferably facial skin; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate ester having an alkenyl chain, or an isomer thereof, or a mixture thereof, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms.

3. A personal cleansing composition for use in a method of treating axillary malodour and killing the growth of bacteria on human skin; wherein the bacteria is C. minutissimum, wherein the personal cleansing composition comprises a salt of an alkenyl sulfate ester having an alkenyl chain, or an isomer thereof, or a mixture thereof, wherein the alkenyl chain comprises 18 to 20 carbon atoms, preferably 18 carbon atoms.

4. The personal cleansing composition according to any one of claims 1 to 3, wherein the salt of the alkenyl sulfate ester having the alkenyl chain, an isomer thereof, a mixture thereof, comprises a sulfate ester group and has the following formula (I): wherein R is an alkenyl chain, and the alkenyl chain comprises 18 to 20 carbon atoms; preferably 18 carbon atoms. (I) 5. The personal cleansing composition according to claim 4, wherein the salt of the alkenyl sulfate ester is selected from the group consisting of alkali metals, ammonium and alkanolamines; preferably wherein the salt of the alkenyl sulfate ester is selected from the group consisting of sodium, potassium, triethylamine and ammonium; more preferably wherein the salt of the alkenyl sulfate ester is selected from the group consisting of sodium and ammonium; most preferably wherein the salt of the alkenyl sulfate ester is sodium.

6. The personal cleansing composition according to any preceding claim, wherein the salt of the alkenyl sulfate ester having the alkenyl chain is present in an amount ranging from 0.01% w / w to 50% w / w; preferably in an amount ranging from 0.01% w / w to 30% w / w; more preferably in an amount ranging from 0.02% w / w to 10% w / w; even more preferably in an amount ranging from 0.05% w / w to 5% w / w; most preferably in an amount ranging from 0.1% w / w to 1% w / w; alternatively wherein the salt of the alkenyl sulfate ester is present in an amount ranging from 0.01% w / w to 5% w / w; preferably in an amount ranging from 0.02% w / w to 3% w / w; more preferably in an amount ranging from 0.05% w / w to 1.5% w / w; even more preferably in an amount ranging from 0.1% w / w to 1% w / w; most preferably in an amount ranging from 0.2% w / w to 0.5% w / w. ​ 7. A personal cleansing composition according to any preceding claim, wherein the salt of the alkenyl sulfate having the alkenyl chain is selected from the group consisting of sodium oleyl sulfate, TEA-oleyl sulfate, ammonium oleyl sulfate, sodium elaidyl sulfate, sodium petroselinyl sulfate, sodium linoleyl sulfate, sodium linolenyl sulfate, sodium gadoleyl sulfate, and mixtures thereof.

8. A personal cleansing composition according to claim 7, wherein the salt of the alkenyl sulfate is selected from the group consisting of sodium oleyl sulfate, TEA-oleyl sulfate, ammonium oleyl sulfate, and mixtures thereof.

9. A personal cleansing composition according to claim 8, wherein the salt of the alkenyl sulfate comprises sodium oleyl sulfate or ammonium oleyl sulfate; preferably wherein the salt of the alkenyl sulfate is sodium oleyl sulfate.

10. A personal cleansing composition according to claim 9, wherein sodium oleyl sulfate is present in an amount ranging from 0.01% w / w to 50% w / w; preferably in an amount ranging from 0.01% w / w to 30% w / w; more preferably in an amount ranging from 0.02% w / w to 10% w / w; even more preferably in an amount ranging from 0.05% w / w to 5% w / w; most preferably in an amount ranging from 0.1% w / w to 1% w / w; alternatively wherein sodium oleyl sulfate is present in an amount ranging from 0.01% w / w to 5% w / w; preferably in an amount ranging from 0.02% w / w to 3% w / w; more preferably in an amount ranging from 0.05% w / w to 1.5% w / w; even more preferably in an amount ranging from 0.1% w / w to 1% w / w; most preferably in an amount ranging from 0.2% w / w to 0.5% w / w.

11. A personal cleansing composition according to any one of claims 7 to 10, wherein sodium oleyl sulfate comprises the cis isomer.

12. A personal cleansing composition according to claim 11, wherein sodium oleyl sulfate comprises a mixture of the cis isomer and the trans isomer, wherein the weight ratio of the cis isomer to the trans isomer is from 8:1 to 99:1 or from 8.5:1 to about 95:1 or from about 8.5:1 to about 9:

1.

13. A personal cleansing composition according to any preceding claim, wherein the composition is in the form of a topical personal cleansing composition, wherein the composition further comprises a dermatologically acceptable carrier for the personal cleansing composition.

14. Non-therapeutic use of a personal cleansing composition for gently cleansing the skin; preferably compared to a control composition comprising 10% sodium lauryl sulfate, 0.05% kathon CG, sufficient citric acid to have a pH of 5.5 ± 0.2 in sufficient water; wherein the personal cleansing composition comprises a salt of an alkenyl sulfate having an alkenyl chain or an isomer thereof or a mixture thereof, wherein the alkenyl chain comprises from 18 to 20 carbon atoms, preferably 18 carbon atoms.

15. Non-therapeutic use of a personal cleansing composition for preventing dryness of the skin; wherein the personal cleansing composition comprises a salt of an alkenyl sulphate having an alkenyl chain comprising from 18 to 20 carbon atoms, preferably 18 carbon atoms, or an isomer thereof, or a mixture thereof.

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