WO2004010985A1

WO2004010985A1 - Personal deodorant

Info

Publication number: WO2004010985A1
Application number: PCT/GB2003/003290
Authority: WO
Inventors: John Adrian Betts
Original assignee: John Adrian Betts
Priority date: 2002-07-29
Filing date: 2003-07-29
Publication date: 2004-02-05
Also published as: AU2003251357A1; GB0217447D0

Abstract

A deodorant active agent comprising a derivative of a mono- or poly- hydroxy aliphatic (acylic) mono- or poly-carboxylic acid in which the hydroxyl group or groups are wholly or partially esterified with a monocyclic or polycyclic aromatic (aroyl) acid in which the carboxyl groups are attached directly or indirectly to the aromatic nucleus and which may have some or all of the constituent hydrogen atoms substituted by other moieties.

Description

PERSONAL DEODORANT

FIELD OF THE INVENTION

This invention relates to derivatives of mono- or poly-hydroxy, mono- or poly- carboxylic acids with anti-microbial, enzyme inhibiting and/or sequestering properties in cosmetic, dermatological and other preparations with the prime purpose of suppressing body odours.

BACKGROUND OF THE INVENTION

The human body has a normal and large population of a number of types of microorganisms. These organisms are nourished by various skin secretions, by skin cell debris and breakdown products, by body secretions and by the organisms themselves. The skin secretions can be conveniently separated into three groups, these being:

(a) Eccrine sweat formed by sweat glands distributed over most of the body surface.

(b) Apocrine sweat produced by apocrine glands located at specific sites on the surface of the body; notably the axillae, the ano-genital area and around the nipples, the normally hirsute areas.

(c) Sebum produced by the sebaceous glands located over most of the body surface except the palms of the hands, the soles of the feet and mucous membranes.

Eccrine sweat is part of the excretory system of the body, working in conjunction with the kidneys to remove excess salts, water and waste products, for example nitrogenous materials such as urea. It also plays a very important role in body temperature regulation. In ideal conditions, eccrine secretions evaporate from the body surface at the same time reducing the body temperature. Eccrine secretion is normally watery, clear and colourless.

Apocrine sweat differs from eccrine sweat in a number of respects. The glands producing apocrine secretions, and thus the amounts of the secretions, are controlled by hormonal and emotional influences. The composition of apocrine secretion is very different from that of eccrine secretion. Normal apocrine secretion is cloudy, somewhat viscous and, at the time of secretion, odourless. It contains water; various lipid materials including glyceride esters of short/medium chain fatty acids; sterol and steroid esters; organic nitrogen compounds including proteins and amino acids; carbohydrates including sugars and various salts. The components provide a nutritious medium for micro-organisms and in the damp, warm conditions met in the axillae and to a lesser extent the ano-genital areas, this growth can take place rapidly. A number of the products resulting from the metabolic processes of these micro-organisms are odorous and can have very strong odours which are nowadays considered unpleasant and socially unacceptable. These odorous products consist of a number of substances including short/medium chain (example Ci- C₈) fatty acids, steroids (example α-androstenol), nitrogen compounds such as indole and organic sulphur compounds such as thiols (mercaptans) and sulphides. Collectively, these materials produce the odour characterised as "body odour".

The secretion from the sebaceous glands, sebum, consists mainly of fatty materials: wax esters; cholesterol, its esters and related compounds; squalene and skin debris. Its function is thought to be that of maintaining the skin and hair in good condition and it normally flows freely from the glands, spreading over the skin surface. Although not a primary cause of body odour, sebum is liberated in the locations of the apocrine glands, and makes a contribution to the skin secretion in that area and is thus subject to the same microorganism attack as the apocrine secretion.

Another body secretion that presents a problem with unpleasant odours is the menses. Menstrual fluid consists of a complex mixture of blood and mucous tissue and is composed of a number of substances including lipids; sterol and steroidal esters; proteins and amino acids and carbohydrates. The damp, warm conditions presented by the pudendum provide a very good reservoir of micro-organisms capable of acting on these secretions, especially the lipids and proteins resulting in the formation malodorous materials, in particular amines.

An odour forming bodily excretion, rather than secretion, is urine and in cases of urinary incontinence common in infants and the elderly, the microbial decomposition of urine deposited on napkins and on clothing can give rise to strong ammoniacal odours. In addition, the ammonia and other substances produced by this decomposition act as skin irritants which left μnchecked can give rise to skin rashes, eczematous skin eruptions and result in secondary infection.

^"From the foregoing, it can be understood that it is desirable to reduce the effects of the micro-organism growth described. Accordingly, astringent basic aluminium or zirconium salts and antimuscarinic (anticholinergic) drugs such as atropine and hyoscine (J. invest. Derm., 1964, 43, 363), likewise potent calcium channel blocking agent drugs such as verapamil derivatives (US 2002/0037264, Unilever Personal Care USA) have hitherto been employed in anhidrotic preparations or else powerful antimicrobial agents such as triclosan [5-chloro-2-(2,4-dichlorophenoxy)phenol] and triclocarban [N-(4-chlorophenyl)-N'-(3,4-di- chlorophenyl)-urea] have been used to suppress this micro-organism development. Concern has been expressed in respect of the safety of many of these materials and methods including the uncertainty of the long term effects of aluminium and zirconium salts on the human body, the acute and chronic toxicity of antimuscarinics and calcium channel blocking drugs, particularly in the presence of underlying disease, and the long term impact both on the human body and on the environment of powerful microbicidal halogenated phenolic compounds, several of these materials already having been banned for general consumer use. Other methods of reducing body odour such as odour masking perfumes and odour absorbing substances such as polymers have been suggested but have had limited success.

It is known that transition series elements, particularly iron and copper, are essential to the growth, nutrition and replication of all living cells and viruses. They form parts of vital co-enzyme systems necessary for a number of metabolic processes. Alterations in the bioavailability of these transition elements thus affect cell function, metabolic processes and other complex phenomena. A number of substances are capable of chelating or sequestering these metallic elements thereby rendering them incapable of exhibiting their normal properties, at least to the extent of acting in the co-enzyme systems and other functions necessary in a living organism. Sequestering or chelating agents have been claimed as components and active ingredients of deodorant preparations as disclosed in GB 1,420,946 (Beecham Group). In this, EDTA (ethylenediaminetetraacetic acid, N,N'-1,2- EthanediylbisfN-(carboxymethyl)-glycine] is said to enhance the efficiency of deodorant compositions containing triclosan as the prime active component. WO 01/52805 (Unilever NV) discloses a number of polyamino-carboxylic acids and particularly DTPA (diethylenetriaminepentaacetic acid, N,N-Bis[2-[bis(carboxymethyl)amino]ethyl]glycine) as an antimicrobial especially in conjunction with a cationic bactericide. WO 02/30383 (Unilever NV) also discloses a number of polyaminocarboxylic acids in conjunction with a phenolic or enolic compound. Exemplified is DTPA in combination with BHT (butylated hydroxytoluene, 2,6-Bis(l,l-dimethylethyl)-4-methylphenol). This combination is said to act as a transferrin dissociation promoter, in turn acting as an anti-microbial and deodorant. US 4,356,190 (Personal Products Company) claims DPTA (diethylenetriaminepentaacetic acid) as an inhibitor of the formation of fatty acids on the skin in the treatment of acne and, by inference in the description, body odour. The aforementioned examples each use amino- polycarboxylic acids as the sequestering agents. It is known that a number of other classes of material act as metal sequestrants, including polycarboxylic acids and these may be exemplified by malonic acid (propanedioic acid), succinic acid (butanedioic acid), glutaric acid (pentanedioic acid) and adipic acid (hexanedioic acid). The sequestering properties are enhanced by the introduction of hydroxyl (OH) groups into the molecule and these compounds are exemplified by tartronic acid (hydroxypropanedioic acid), malic acid (hyroxybutanedioic acid), tartaric acid (2,3-dihydroxybutanedioic acid) and citric acid (2- hydroxypropane-l,2,3-tricarboxylic acid). A number of these substances are well known and widely used in many industries as sequestering agents. WO 97/02010 (The Procter and Gamble Company) discloses the use of a chelant selected from the succinic acid, glutaric acid, phosphonic acid classes or any salts thereof and mixtures thereof as a bactericidal compound. One chelant salt is exemplified, trisodium ethylenediamine disuccinate. A number of compounds of relatively complex chemical structure are claimed as having chelation affinity for a variety of end uses, including personal care and deodorants, in US 6,387,891 (Concat Ltd.)

In addition to the above noted methods, there are a number of specifications claiming the use of certain esters of hydroxycarboxylic acids, for example triethyl citrate, as "non- microbicidal deodorants" which are described in Cosmetics and Toiletries, 1980, 95, 48 - 50 and disclosed in US 4,010,253 (Henkel & Cie GmbH). Developments of this original invention are disclosed in US 4,675,177 (American Cyanamid Company), US 5,968,488 (Henkel Kommanditgesellschaft auf Aktien), US 5,770,185 (Henkel Kommanditgesellschaft auf Aktien) and US 6,277,359 (Cognis Deutschland GmbH). The deodorant properties of these esters has been attributed to extra-cellular microbial enzymes (esterases, including proteases and Upases) acting to cleave the constituents of the ester into its component acid and alcohol. The released alcohol then acts as an anti-microbial and the released acid acts to alter the pH conditions of the immediate environment. Both of these inhibit further microorganism growth. After a period of time by reasons of evaporation of the released alcohol and neutralisation of the released acid by the natural buffering processes, the "micro- environment" reverts and the hydrolysis process may be repeated until the active ingredient is exhausted. In the example given with triethyl citrate, there is no immediate sequestering action as the sequestering property of this acid in its ionised state is lost in the removal of the free carboxyl group by the esterification. The esterase concept is developed in a system with improved activity and disclosed in PCT/GB90/01750 (Publication No. WO 91/07165) (Robertet SA). This describes the use of a benzyl or phenyl benzoyloxybenzoate ester which is hydrolysed by microbial extra-cellular esterases to produce three mononuclear benzene compounds, between them bearing at least two hydroxyl and two carboxyl substances which impart an antimicrobial action. It is stated that these compounds have a more prolonged deodorant action than the simple ester systems.

SUMMARY OF THE INVENTION It is the aim of the present invention to provide a means of reducing the growth and activity of the micro-organisms involved in the formation of body odour, with the specific objective of providing a personal deodorant which offers an efficient action over a substantial period of time.

According to the present invention there is provided a deodorant active agent comprising a derivative of a mono- or poly- hydroxy aliphatic (acylic) mono- or polycarboxylic acid in which the hydroxyl group or groups are wholly or partially esterified with a monocyclic or polycyclic aromatic (aroyl) acid in which the carboxyl groups are attached directly or indirectly to the aromatic nucleus and which may have some or all of the constituent hydrogen atoms substituted by other moieties.

Preferred embodiments of the present invention are recited in Claims 2 to 21 below.

In another aspect of the invention there is provided a method of reducing body odour involving the deodorant active agent as described in any of Claims 1 to 13 being topically applied to human skin.

In another aspect of the present invention there is provided a cosmetically acceptable deodorant product as claimed in any of Claims 14 to 21 below.

We have discovered that if some or all the hydroxyl groups of a mono- or polyhydroxy aliphatic (acylic) mono- or poly- carboxylic acid are esterified with an aromatic (aroyl) acid, a chemically defined compound is produced which has inherent anti-microbial, esterase inhibiting and sequestering properties. The acids of the present invention differ substantially from those of previous inventions, example US 5,770,185 (Henkel Kommanditgesellschaft auf Aktien), by containing within the molecule an anti-microbially active aromatic (aroyl) group esterified with the acyl acid hydroxyl groups. Additionally, the carboxyl groups of the acyl acid of the present invention can be free and available to lower the hydrogen ion concentration (pH) of the surrounding medium, to enable salt formation to give increased aqueous solubility, and to allow the metal sequestering properties to be utilised. The present invention is understood to include the esters of the described aroyl substituted acyl carboxylic acids

From the preamble, it will be appreciated that the properties described in the previous paragraph are each of relevance in a deodorant preparation and the compositions of the present invention perform unexpectedly well in terms of reducing and maintaining low body odour. Without being constrained by theory, it is hypothesised that after the reduction of microbial numbers by, for example, washing with a conventional soap or detergent product, one or several of a number of actions may occur. In no specific order of priority, these are:

(1) The sequestering properties inhibit the uptake of transition metal ions necessary for the development of the remaining micro-organisms thereby minimising their re-growth.

(2) The intrinsic anti-microbial properties inhibit development of micro-organisms.

(3) Esterases produced by micro-organisms hydrolyse the ester linkage of the subject material and thereby release an active anti-microbial compound.

(4) The acidic nature of the subject material and of the hydrolysed subject material as in (3) above creates unsuitable conditions for continued microbial growth.

DESCRIPTION OF THE INVENTION

Embodiments of the present invention will now be described by way of example.

The present invention relates to cosmetic and dermatological deodorant preparations containing derivatives of mono- or poly-hydroxy carboxylic (acylic) acids esterified with aromatic (aroyl) acids whereby the hydroxyl groups of the acylic acid are partially or wholly substituted by aroyl groups. The carboxyl group(s) of the acylic acid may be wholly or partially (if in plurality) esterified.

The acylic hydroxy acids within the meaning of the present invention are defined as compounds of one or more linear or branched carbon atoms to which are attached at least one carboxyl group (COOH) and at least one hydroxyl group (OH). The hydroxyl group may or may not be attached to the same carbon atom as the carboxyl group. The simplest parent acid fitting within this definition is glycolic acid (hydroxyethanoic acid, HOCH₂COOH). Other homologous acids, included as examples but not an exhaustive list, are lactic acid (2- hydroxy-propanoic acid, CH₃CHOHCOOH), β-hydroxybutyric acid (3-hydroxybutanoic acid, CH₃CHOHCH₂COOH). Several of these acids are found in nature, for example glycolic acid is found in beet {Beta vulgaris L., Chenopodiaceae) juice and sugar cane {Saccharum officinarum L., Gramineae) juice. Lactic acid is found in fermented milk. These acids are not noted for sequestering properties and this aspect is notably improved when there is contained within the parent acid molecule a plurality of either or both hydroxyl (-OH) groups and carboxyl (-COOH) groups. An illustrative but not comprehensive list of acids fitting this definition includes tartronic acid (hydroxypropanedioic acid), malic acid (hydroxybutanedioic acid), tartaric acid (2,3-dihydroxybutanedioic acid), citric acid (2- hydroxypropane-l,2,3-tricarboxylic acid), gluconic acid (1,2,3,4,5-pentahydroxyhexanoic acid). A number of the acids within this definition are widely distributed in nature with malic, tartaric and citric acids being colloquially known as "fruit acids" as significant quantities are to be found in apples, grapes and citrus fruits respectively. As well as being approved food ingredients, these acids have many industrial, medicinal and cosmetic uses.

The aromatic (aroyl) acids within the meaning of the present invention are comprised of compounds containing one or more carboxyl groups attached directly or indirectly to an aromatic (aryl or benzenoid) nucleus. This nucleus may be mono- or poly- cyclic with the aromatic rings fused or in chains. In addition, any or all of the hydrogen atoms of the aromatic ring may be substituted by a halogen (F, CI, Br, I) atom, by a C_\ _ alkyl or alkoxy group or by a hydroxyl (-OH) group or any combination of these. The simplest acid complying with this definition is benzoic acid (benzenecarboxylic acid). Other acids, by way of example but not exclusively, are toluic acid (methylbenzoic acid, -CH₃ substitution), anisic acid (methoxybenzoic acid, -OCH₃ substitution), salicylic acid (hydroxybenzoic acid, -OH substitution), cinnamic acid (phenylpropenoic acid), phenylacetic acid and mandelic acid (phenylhydroxyacetic acid). A number of these acids are widely distributed in nature and found in many foodstuffs, spices and oleoresins. They have anti-microbial properties which are utilised, in pharmaceutical preparations for example, as the active components in anti- fungal and anti-bacterial products and as anti-microbial preservatives; in foodstuffs as antimicrobial preservatives and flavouring agents and in cosmetics as antimicrobial preservatives.

The mono- or poly-hydroxy carboxylic (acylic) acids esterified with aromatic acids within the meaning of the present invention may by prepared by conventional methods known by those skilled in the art, which may be that of the Schotten-Baumann reaction (C. Schotten, Ber.17, 2544 (1884), E. Baumann, Ber. 19, 3218 (1886)) or modifications thereof. A number of compounds have been prepared that conform to the requirements of the present invention and certain ones stand out as being of easy synthesis and all those investigated have the newly discovered enhanced deodorant properties.

The aroyl derivatives of tartaric acid ((2,3-dihydroxybutanedioic acid) have been found to have exceptional deodorant properties and are relatively easy to manufacture. The simplest tartaric acid derivative conforming to the present invention is dibenzoyl tartaric acid. This has been discovered to have an exceptionally high deodorant activity both in terms of efficacy and persistence of effect. It is also relatively easy and economical to manufacture from readily available starting materials. A large number of tartaric acid derivatives conforming to the requirements of the present invention have been synthesised on an experimental basis and many, for example ditoluoyl tartaric acid and dianisoyl tartaric acid, show similar enhanced deodorant activities but, by having more costly starting materials, are considered to be less economical in manufacture and use.

Those skilled in the art will recognise that tartaric acid exists in various isomeric forms. It has been found that, as far as can be ascertained, there is no demonstrable difference in the enhanced deodorant activity between dibenzoyl-D-tartaric acid and dibenzoyl-L-tartaric acid. For the purposes of the present invention, it is to be understood that the term dibenzoyl tartaric acid, and the abbreviation DBTA, embrace the benzoyl derivatives of all tartaric acid isomers, although the L-derived form is the most desirable as it is from the "natural" isomer and is the most cost-effective.

Those skilled in the art will also recognise that the acids of the present invention have one or more free carboxyl groups which may be neutralised. By way of example, disodium dibenzoyl tartrate, sodium hydrogen dibenzoyl tartrate, dipotassium benzoyl tartrate, potassium hydrogen benzoyl tartrate and also the ammonium and amine salts formed by the neutralisation with ammonia or with cosmetically acceptable amines and alkanolamines can readily be formed. It will be appreciated that mixed salts are included in this category for example, sodium potassium dibenzoyl tartrate.

In addition, the free carboxyl groups of the acids that are the subject of the present invention are capable of being esterified. For the purposes of the present invention, these esters are understood as being derived from Ci - C₁₈ branched or linear fatty alcohols, aromatic alcohols or phenols. It should be understood that this esterification diminishes the sequestering properties of the invention but normally enhances the anti-microbial qualities.

The acids associated with the present invention with more than two carboxyl groups, for example citric acid (three carboxyl groups) may have one, two or three carboxyl groups neutralised or esterified with the same or different reactants.

_. The materials of the present invention are intended to be used in cosmetic and dermatological preparations with the intention of reducing body odour. Examples of the types of products that may contain the invention include aerosols, squeeze and pump sprays; wax based, soap based, compressed powder based and dibenzylidine sorbitol based sticks; roll-on suspensions, solutions and emulsions; creams, gels and lotions; talc and dusting powders. The acids of the present invention, their salts and other derivatives may also be incorporated into soap bars, synthetic detergent based cleansing bars, and soap or detergent based liquid cleansing products such as shower gels, foam baths, hand and body washing products. Some cosmetic compositions containing the present invention will now be described by way of example:

As a personal deodorant for use in an aerosol spray or mechanical pump spray container, 0-1 to 10%, more preferably 0-1 to 2-0% most preferably 0-1 to 1-0% of DBTA is dissolved in 96% ethanol. Suitable perfumes, emollient materials and colours may be included as required. The resulting solution is then charged into suitable aerosol containers with an appropriate propellant or into mechanical pump spray containers, according to conventional techniques. In this example, the ethanol has a powerful but short lived deodorant effect by way of a direct microbicidal action. The DBTA provides a "reservoir" of active material for a long-lasting deodorant action. In this example, part of the alcohol may be replaced by water to the limits imposed by the solubility of the DBTA in alcohol water mixtures. Excess water should be avoided as the product may become cosmetically unacceptable because of prolonged drying times after application. As a personal deodorant in roll-on form, 0-1 to 10%, more preferably 0-1 to 2-0% most preferably 0-1 to 1-0% of DBTA may be dissolved in an alcoholic or aqueous/alcoholic solvent and thickened with an alcohol and/or water soluble cellulose ether derivative such as hydroxypropylcellulose or hydroxyethylcellulose.

As a deodorant for areas proximate to, and including, the pudendum, and for reducing the odour of the menstrual fluid, the materials of the present invention may be applied, for example, as an aqueous/alcoholic solution; as an aqueous/alcoholic solution in a spray or aerosol; in finely divided form in a talc or dusting powder; or pre-applied to catamenial devices such as tampons or sanitary napkins. Other materials may be present to form a cosmetically acceptable preparation.

Addressing the odours associated with urinary incontinence, the materials related to the present invention may be incorporated into a cosmetically and dermatologically acceptable cream, lotion, spray or dusting powder. The products may also be applied to napkins, pads and waterproof pant-liners to inhibit the growth of the micro-organisms responsible for the formation of urinary malodours.

For use in aqueous products where the concentration of DBTA exceeds its solubility, the free acid form of the DBTA may be wholly or partially neutralised to form the salt or the half salt, this last meaning the neutralisation of one carboxyl group of the DBTA. Neutralisation to the salt form maintains the chelating function.

. DBTA and the other acids of the present invention so far investigated are compatible with the other cosmetic raw materials used in deodorant preparations including emollient fatty esters; fatty alcohols; fatty acids; sorbitan ethers and ethoxylates; ethoxylated fatty acids and alcohols; propoxylated fatty acids and alcohols; mineral oil and mineral spirits; aerosol propellants including propane, butane and pentane and their isomers, dimethyl ether, hydrofluorocarbons and the gaseous propellants such as nitrogen, nitrous oxide and carbon dioxide; most anionic, cationic and non-ionic synthetic detergents; glycerine, other glycols and glycol ethers; mineral based rheology control agents; cellulose ethers; steric hindered phenols for example BHT, used as antioxidants; other antioxidants such as gallate esters, tocopherols, esters of ascorbic acid and many others.

The acids of the present invention are compatible with, and may be admixed with, other materials used as deodorants, for example: phenolic and cationic bactericides; biguanides; phenolic ethers (example phenoxyethanol and phenoxypropanol); farnesol (3,7,11-trimethyl 2,6,10-dodectrien-l-ol); glyceryl monolaurate and similar fatty triglyceride deodorants; esterase inhibiting esters such as triethyl citrate; perfume raw materials and compounds; astringent aluminium and zirconium salts used as antiperspirant active materials, and with zinc and other salts used as inorganic deodorants. Some sequestering activity may be lost by prior reaction with the aluminium, zirconium or zinc in these inorganic preparations but there remain the enzyme inhibiting and anti-microbial features.

The free acids of the present invention, for example DBTA, are not compatible per se with alkalis, amines and other bases. The neutralised or half neutralised salts formed by reaction with bases present in a preparation will most likely be compatible.

TESTING FOR DEODORANT EFFECT

Twenty volunteer testers (10 male, 10 female) who normally used a deodorant product or "body spray" rather than an anti-perspirant or antiperspirant/deodorant were supplied with unperfumed soap (Simple Soap™ [Accantia Health & Beauty Products Ltd.]) for washing the axillae during the week prior to assessment. They were also supplied with a pump spray containing 96% denatured ethanol (Ethanol B, [US: SD Alcohol 40]) for use as a control deodorant which they were permitted to use ad libitum as deemed necessary. They were also instructed to avoid any perfumed products as far as possible. The ethanol only "deodorant" was used to avoid any residual (non volatile) deodorant active material remaining on the skin immediately prior to the tests whilst maintaining social acceptability for the testers. At the start of the tests, the testers were provided with two pump sprays identified as "A" and "B". One spray consisted of DBTA at 0-5% in 96% denatured ethanol the other spray contained 96% denatured alcohol only. The testers were not made aware of which spray contained the active ingredient (blind test). The testers were instructed to use their normal washing routine using the unperfumed soap and apply the test spray in the same way, as far as possible, as their normal deodorant product. They were also instructed to note which coded spray was used on which axilla and to maintain that throughout the period of the testing. The sprays were permitted to be used once only per twenty-four-hour period. The effectiveness of the sprays was carried out by self assessment at 0 hours (after allowing the alcohol to evaporate), 12 hours and 24 hours and records made. The testing was carried out over a period of seven days. For the purposes of these tests with female testers, times of ovulation and menstruation were avoided as far as possible.

At the end of the test the volunteers were requested to complete a questionnaire: How long was it before you knew which the "active" spray was?

12 hours or less

12 - 24 hours

Longer than that

Don't know

How good do you think this product is as a deodorant?

Excellent

Good

Fairly good

Useless

How do you rate this product against your usual deodorant?

Better

As good

About the same

Not as good

Do you think you would you buy a product containing this active ingredient if it were available?

Definitely Probably Possibly

No

Any other comments? Questions posed during the period of the test showed that after a 12 hour period, fourteen testers (70%) stated the active product was noticeably better. After a period of 24 hours, all testers (100%) agreed the active product containing 0-5% DBTA was radically better than the alcohol control alone.

The replies to the questionnaire were scored on a scale of 1 - 4 with 1 representing negative attributes, 4 the most positive. Question 1 achieved a mean of 3-6, question 2 gave 3-2, question 3 gave 3-0 and question 4 gave 3-2. None of the questions elicited a "1" score from any of the testers. The overall score was 3-25.

Further to the tests described above, two volunteers tested the longevity of a single application of a spray product containing DBTA at 0-5%. This testing was performed immediately after the tests as above and was again based on self-assessment. Tester 1 assessed the product from one application on to both freshly washed axillae as being effective for thirty six hours; tester 2 for a longer time period.

The above embodiment is described by way of example only. Many variations are possible without departing from the invention as defined by the following claims.

Claims

1. A deodorant active agent comprising a derivative of a mono- or. poly- hydroxy aliphatic (acylic) mono- or poly-carboxylic acid in which the hydroxyl group or groups are wholly or partially esterified with a monocyclic or polycyclic aromatic (aroyl) acid in which the carboxyl groups are attached directly or indirectly to the aromatic nucleus and which may have some or all of the constituent hydrogen atoms substituted by other moieties.

2. The deodorant active agent according to claim 1 wherein the mono- or poly- hydroxy aliphatic (acylic) mono- or poly carboxylic acid is selected from any one of hydroxyethanoic acid (glycolic acid), hydroxypropanoic acid (lactic acid), β-hydroxybutyric acid, γ- hydroxybutyric acid, hydroxypropanedioic acid (tartronic acid), hydroxybutanedioic acid (malic acid), 2,3,-dihydroxybutanedioic acid (tartaric acid), 2-hydroxypropane-l,2,3-tricarboxylic acid (citric acid), or 1,2,3,4,5-pentahydroxyhexanoic acid (gluconic acid).

3. The deodorant active agent according to Claim 1 or 2 wherein the aromatic (aroyl) acid is selected from any one of benzenecarboxylic acid (benzoic acid), 1, 2 or 3-methylbenzoic acid {o, m or /?-toluic acid), 1, 2 or 3-methoxybenzoic acid {o, m or -anisic acid), 1- hydroxybenzoic acid (salicylic acid), 3-hydroxybenzoic acid, phenylpropenoic acid (cinnamic acid), phenylacetic acid, phenylhydroxyacetic acid (mandelic acid) or 1 or 2-naphthalene carboxylic acid ( or β-naphthoic acid).

4. The deodorant active agent according to any of Claims 1 to 3 wherein any or all of the hydrogen atoms of the aromatic acid are substituted by a halogen (F, CI, Br, I) atom, by a C^ alkyl or alkoxy group or by a hydroxyl group or any combination of these.

5. A deodorant active agent according to any of Claims 1 to 3 comprising 2,3-dibenzoyl tartaric acid.

6. A deodorant active agent according to any of Claims 1 to 3 comprising 2,3-ditoluoyl tartaric acid.

7. A deodorant active agent according to any of Claims 1 to 3 comprising 2,3-dianisoyl tartaric acid.

8. A deodorant active agent according to any of Claims 1 to 3 comprising 2,3- dinaphthoyl tartaric acid.

9. A deodorant active agent according to any of Claims 1 to 3 comprising 2-benzoyl citric acid.

10. A deodorant active agent according to any of Claims 1 to 3 comprising 2-toluoyl citric acid.

11. A deodorant active agent according to any of Claims 1 to 3 comprising 2-anisoyl citric acid.

12. The deodorant active agent according to any preceding claim wherein one or more of the carboxyl groups are esterified with Cι_s alcohol.

13. The deodorant active agent according to any preceding claim wherein the one or more of the carboxyl groups are neutralised by a metal, ammonia, an amine or an alkanolamine.

14. A cosmetically acceptable deodorant product containing the deodorant active agent according to any preceding claim at a concentration of 0-1 to 10%

15. A cosmetically acceptable deodorant product containing the deodorant active agent according to any one of claims 1 to 13 at a concentration of 0-1 to 2%

16. A cosmetically acceptable deodorant product containing the deodorant active agent according to any one of claims 1 to 13 at a concentration of 0-1 to 1%

17. A cosmetic product according to any of Claims 14 to 16 comprising a C₂ _ ₄ alcohol solution of the deodorant active agent.

18. A cosmetic product according to any of Claims 14 to 17 comprising the deodorant active agent in any other suitable vehicle for application to the human skin or proximate to the human skin.

19. A cosmetic product according to any of Claims 14 to 18 comprising the deodorant active agent in combination with one or more phenolic and cationic bactericide; biguanide; phenolic ether; farnesol (3,7,11-trimethyl 2,6,10-dodectrienol-l-ol); glyceryl monolaurate and other fatty glyceride deodorants; esterase inhibiting compounds; perfume raw materials and compounds.

20. A cosmetic product according to any of Claims 14 to 19 comprising the deodorant active agent in combination with one or more aluminium, zirconium or zinc compound used as antiperspirant active materials.,

21. A cosmetic product according to any of Claims 14 to 20 further comprising one or more of the following: water, perfumes, emollients, skin conditioning agents.

22. A method of reducing body odour involving the deodorant active agent of any of Claims 1 to 13 being topically applied to human skin.