WO2011047420A1 - Cosmetic compositions - Google Patents

Abstract

A topical antimicrobial composition including (i) a polymer of 2-propenal, and (ii) a C_3-10 alkanediol.

Description

Cosmetic Compositions

Field

[0001] The present invention relates to topical antimicrobial compositions. The present invention also relates to topical antibacterial, antiviral and antifungal compositions. Additionally, the present invention relates to methods for inhibiting the proliferation of microbes on the skin, including methods for inhibiting the proliferation of fungus on the skin, methods for inhibiting the proliferation of virus on the skin and methods for inhibiting the proliferation of bacteria on the skin. The present invention also relates to anti- dandruff compositions, anti-acne compositions and anti-dermatitis compositions, and methods for the treatment or prevention of dandruff, acne and dermatitis.

Background

[0002] Impeding the spread of infectious disease is vital from a moral, public health and economic standpoint. The widespread use of topical antimicrobial compositions such as hand cleansers is one effective means of impeding the spread of infectious diseases. As such, the development of new topical antimicrobial compositions is of significant importance.

[0003] Topical antimicrobial compositions are not only useful in prophylactic applications such as hand cleansers, but are also important in treating conditions of the skin which are caused by bacteria, virus or fungi. Skin infections can lead to considerable discomfort for the sufferer, be unsightly and can be difficult to contain in some circumstances. Common skin infections include, but are not limited to, acne, rosacea, impetigo, folliculitis, furunculosis, ecthyma, eczema, psoriasis, atopic dermatitis, seborrhoeic dermatititis, herpes, epidermolysis bullosa, pityriasis versicolor, tinea and icthyosis. Topical antimicrobial compositions are also useful for preventing or treating infection of traumatic lesions (such as ulcers, minor burns, cuts, abrasions, lacerations, wounds, biopsy sites, surgical incisions and insect bites).

[0004] Skin related disorders such as dermatitis, acne and dandruff can cause significant discomfort and displeasure to sufferers. In addition to the physical discomfort experienced, many sufferers also experience psychological or social difficulty which can be associated with the aesthetic impact of these conditions. As such, it is important to develop new treatments which are able to reduce or remove the effects of these conditions.

[0005] Alkanediols, particularly 1 ,2-alkanediols having 6 to 10 carbons have some antimicrobial properties and as such may be useful in the treatment of some skin related disorders. For example, the minimum inhibitory concentration (MIC) values for 1 ,2- hexanediol and 1 ,2-octanediol against E.coli have been reported to be 10,000 ppm and 6,300 ppm respectively (Pillai, R, Schmaus G, Pfeiffer A, Lange S and Trunet A, Cosmetics and Toiletries magazine (2008) 123(10): 53-64) and (Kinnunen T. and Koskela M. Acta Derm Venereol (Stockh) (1991 ) 71 (2): 148-150.

[0006] The applicants have discovered that co-formulations which incorporate C_3-ioalkanediols with certain types of polymer result in significantly improved effectiveness in inhibiting the proliferation of microbes. These formulations may also be useful in the treatment of a number of skin related disorders such as acne, dandruff and dermatitis.

[0007] The discussion of the background to the invention herein is included to explain the context of the invention. This is not to be taken as an admission that any of the material referred to was published, known or part of the common general knowledge as at the priority date of any of the claims.

Summary of the Invention

[0008] The present invention relates to a topical antimicrobial composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

[0009] In some embodiments of the topical antimicrobial compositions of the invention, the C3-io alkanediol in the composition includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4- butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4- pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7- heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9 nonanediol, 1 ,2-decanediol, 1 ,10- decanediol and neopentyl glycol. In some particular embodiments the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

[0010] In some particular embodiments of the invention the C-3-ιο alkanediol includes at least one 1 ,2-C3-ioalkanediol. In some embodiments, the 1 ,2-C3-ioalkanediol can be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2-nonanediol and 1 ,2-decanediol. In some cases the C3-10 alkanediol is a 1 ,2-C3-ioalkanediol selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

[0011] Polymers of 2-propenal may be formed by radical or anionic polymerization and generally speaking have different structures and physical properties. The polymer of 2-propenal is preferably one formed by anionic polymerization. Such polymers typically comprise monomeric units linked through oxygen-carbon polymerization as well as carbon-carbon polymerization. Thus, the anionic polymerization results in both polymerization through the vinyl group of acrolein as well as the aldehyde and hence both forms are present. The polymers of 2-propenal may be homopolymers or copolymers. Examples of copolymers include copolymers formed with alcohols such as C2 to C10 alkane diols, polyethylene glycol, hydroxy carboxylic acids, such as tartaric acid, ascorbic acid and mixtures thereof.

[0012] The polymer of 2-propenal topical antimicrobial typically comprises polymer repeating unit comprising at least one unit type selected from

wherein R is H or Ci_-4 alkyl, and the hydrated, hemiacetal and acetal forms of the repeating unit.

[0013] In some embodiments of the compositions of the invention, R is hydrogen.

[0014] The polymer of 2-propenal may be a homopolymer or copolymer and in a particularly preferred embodiment the polymer of 2-propenal is poly(2-propenal, 2- propenoic acid). Poly(2-propenal, 2-propenoic acid) is preferably formed by oxidation of a poly(2-propenal), preferably formed by anionic polymerization, so as to introduce carboxyl groups. The poly(2-propenal, 2-propenoic acid) may comprise, for example, from 0.1 to 5 moles of carboxyl groups per kilogram of polymer.

[0015] In some embodiments of the invention the polymer of 2-propenal is poly(2- propenal, 2-propenoic acid).

[0016] In some embodiments the topical antimicrobial composition includes from 0.01 to 10 wt% of the polymer of 2-propenal based on the total weight of the composition. In some specific cases the composition includes from 0.05 to 5 wt% of the polymer of 2- propenal.

[0017] The topical antimicrobial compositions of the invention typically include from 0.1 to 99.99 wt% of the C3-ioalkanediol based on the total weight of the composition. In some specific cases the compositions include from 1 to 80 wt% of the C3-ioalkanediol. In other cases the compositions include from 1 to 50 wt% of the C_3-i₀alkanediol. In some specific embodiments the compositions include from 1 to 20 wt% of the C3-ioalkanediol.

[0018] Topical antimicrobial compositions of the invention may further include a C2- i₀alkanol. In some specific embodiments, the C_2-ioalkanol is selected from the group consisting of ethanol and isopropanol. In some specific embodiments the ratio of the C3- ioalkanediol to the

is between 1 :10 and 10:1 . [0019] Topical antimicrobial compositions of the invention may further include one or more of a dermatologically acceptable carrier, a stabilizing agent, a thickening agent, a preservative, a skin or hair cleansing agent, a skin softening agent, fragrance, a dye or a pigment.

[0020] The invention also relates to methods for inhibiting the proliferation of microbes on the skin which include applying to the skin an inhibitory-effective amount of a topical microbial composition according to the invention.

[0021] The invention also relates to a method for inhibiting the proliferation of microbes on the skin including applying to the skin an inhibitory-effective amount of a topical microbial composition including (i) a polymer of 2-propenal, and (ii) a C-3-ιο alkanediol. In some embodiments of the method, the C3-10 alkanediol in the composition includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3- propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol. In some specific embodiments the C-3-ιο alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol. In some embodiments the C3-ioalkanediol is a 1 ,2-C-3-ioalkanediol. The 1 ,2-C3-ioalkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2- pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2-nonanediol and 1 ,2-decanediol. In some cases the 1 ,2-C_3-i₀alkanediol is selected from the group consisting of 1 ,2- propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

[0022] In some embodiments the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

[0023] The present invention also relates to the use of (i) a polymer of 2-propenal and (ii) a C3-ioalkanediol in the manufacture of a topical medicament for inhibiting the proliferation of microbes on skin. In some embodiments the C-3-ιο alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3- propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol. In some specific cases the C_3-i₀ alkanediol is selected from the group consisting of 1 ,2- propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol. In some embodiments the polymer of 2-propenal used in the manufacture of the medicament is poly(2-propenal, 2-propenoic acid).

[0024] In some embodiments the C3-ioalkanediol used in the manufacture of the topical medicament is a 1 ,2-C3-ioalkanediol. The 1 ,2-C3-ioalkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2- pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2-nonanediol and 1 ,2-decanediol. In some particular cases the 1 ,2-C3-ioalkanediol used in the manufacture of the topical medicament may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

[0025] The present invention also relates to an anti-dandruff composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

[0026] In some embodiments of the anti-dandruff compositions of the invention the C-3-ιο alkanediol in the composition includes at least one compound selected from the group consisting of 1 ,2-ethanediol, 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3- butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4-pentanediol, 1 ,5- pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6-hexanediol, 2,5- hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9 nonanediol, 1 ,2- decanediol, 1 ,10-decanediol and neopentyl glycol. In some particular embodiments the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol. [0027] In some particular embodiments of the anti-dandruff compositions of the invention the C-3-10 alkanediol includes at least one 1 ,2-C_3-i₀alkanediol. In some embodiments, the 1 ,2-C3-ioalkanediol can be selected from the group consisting of 1 ,2-propanediol, 1 ,2- butanediol, 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2- nonanediol and 1 ,2-decanediol. In some cases the C-3-ιο alkanediol is a 1 ,2-C3- i₀alkanediol selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2- hexanediol and 1 ,2-octanediol.

[0028] In some embodiments of the anti-dandruff compositions of the invention, the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

[0029] In some embodiments the anti-dandruff composition includes from 0.01 to 10 wt% of the polymer of 2-propenal based on the total weight of the composition. In some specific cases the composition includes from 0.05 to 5 wt% of the polymer of 2-propenal.

[0030] The anti-dandruff compositions of the invention typically include from 0.1 to 99.99 wt% of the C3-ioalkanediol based on the total weight of the composition. In some specific cases the compositions include from 1 to 80 wt% of the C3-ioalkanediol. In other cases the compositions include from 1 to 50 wt% of the C_3-i₀alkanediol. In some specific embodiments the compositions include from 1 to 20 wt% of the C_3-ioalkanediol.

[0031] Anti-dandruff compositions of the invention may further include a

In some specific embodiments, the C₂-ioalkanol is selected from the group consisting of ethanol and isopropanol. In some specific embodiments the ratio of the C3-ioalkanediol to the C2-ioalkanol is between 1 :10 and 10:1 .

[0032] Anti-dandruff compositions of the invention may further include one or more of a dermatologically acceptable carrier, a stabilizing agent, a thickening agent, a preservative, a skin or hair cleansing agent, a skin softening agent, fragrance, a dye or a pigment. [0033] The invention also relates to methods for treating or preventing dandruff which include applying to the scalp a therapeutically or prophylactically effective amount of an anti-dandruff composition according to the invention.

[0034] The invention also relates to a method for treating or preventing dandruff including applying to the scalp a therapeutically or prophylactically effective amount of an anti- dandruff composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol. In some embodiments of the method, the C3-10 alkanediol in the composition includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3- propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol. In some specific embodiments the C_3-i₀ alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol. In some embodiments the C3-ioalkanediol is a 1 ,2-C-3-ioalkanediol. The 1 ,2-C3-ioalkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2- pentanediol,

1.2- hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2-nonanediol and 1 ,2-decanediol. In some particular cases the 1 ,2-C_3-i₀alkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

[0035] In some embodiments of the methods of treating or preventing dandruff, the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

[0036] The present invention also relates to use of (i) a polymer of 2-propenal and (ii) a C3-ioalkanediol in the manufacture of a medicament for treating or preventing dandruff. In some embodiments the C_3-i₀ alkanediol used in the manufacture of the medicament includes at least one compound selected from the group consisting of 1 ,2-propanediol,

1.3- propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1,6-hexanediol, 2,5-hexanediol, 1,7-heptanediol, 1 ,2-octanediol, 1,8- octanediol, 1,9 nonanediol, 1 ,2-decanediol, 1,10-decanediol, and neopentyl glycol. In some specific cases the C_3-i₀ alkanediol is selected from the group consisting of 1,2- propanediol, 1,3-butanediol, 1,2-hexanediol and 1,2-octanediol. In some embodiments the polymer of 2-propenal used in the manufacture of the medicament for treating or preventing dandruff is poly(2-propenal, 2-propenoic acid).

[0037] In some embodiments the C3-ioalkanediol used in the manufacture of the medicament for treating or preventing dandruff is a 1 ,2-C3-ioalkanediol. The 1,2-C3- ioalkanediol may be selected from the group consisting of 1,2-propanediol, 1,2- butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2- nonanediol and 1,2-decanediol. In some particular cases the 1 ,2-C3-ioalkanediol used in the manufacture of the medicament for treating or preventing dandruff may be selected from the group consisting of 1,2-propanediol, 1,2-butanediol, 1,2-hexanediol and 1,2- octanediol.

[0038] In some embodiments of the anti-acne compositions of the invention the C-3-ιο alkanediol in the composition includes at least one compound selected from the group consisting of 1 ,2-ethanediol, 1,2-propanediol, 1 ,3-propanediol, 1,2-butanediol, 1,3- butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentanediol, 1 ,4-pentanediol, 1,5- pentanediol, 2,4-pentanediol, 1,2-hexanediol, 1 ,5-hexanediol, 1,6-hexanediol, 2,5- hexanediol, 1,7-heptanediol, 1,2-octanediol, 1 ,8-octanediol, 1,9 nonanediol, 1,2- decanediol, 1,10-decanediol and neopentyl glycol. In some particular embodiments the C-3-10 alkanediol is selected from the group consisting of 1,2-propanediol, 1,3-butanediol, 1,2-hexanediol and 1,2-octanediol.

[0039] In some particular embodiments of the anti-acne compositions of the invention the C-3-10 alkanediol includes at least one 1,2-C_3-i₀alkanediol. In some embodiments, the 1,2- C3-ioalkanediol can be selected from the group consisting of 1,2-propanediol, 1,2- butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2- nonanediol and 1,2-decanediol. In some cases the 1,2-C3-ioalkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.

[0040] In some embodiments of the anti-acne compositions of the invention, the polymer is poly(2-propenal, 2-propenoic acid).

[0041] In some embodiments the anti-acne composition includes from 0.01 to 10 wt% of the polymer of 2-propenal based on the total weight of the composition. In some specific cases the composition includes from 0.05 to 5 wt% of the polymer of 2-propenal.

[0042] The anti-acne compositions of the invention typically include from 0.1 to 99.99 wt% of the C3-ioalkanediol based on the total weight of the composition. In some specific cases the compositions include from 1 to 80 wt% of the C3-ioalkanediol. In other cases the compositions include from 1 to 50 wt% of the C3-ioalkanediol. In some specific embodiments the compositions include from 1 to 20 wt% of the C_3-i₀alkanediol.

[0043] Anti-acne compositions of the invention may further include a C2-ioalkanol. In some specific embodiments, the C2-ioalkanol is selected from the group consisting of ethanol and isopropanol. In some specific embodiments the ratio of the C3-ioalkanediol to the C_2-ioalkanol is between 1 :10 and 10:1 .

[0044] Anti-acne compositions of the invention may further include one or more of a dermatologically acceptable carrier, a stabilizing agent, a thickening agent, a preservative, a skin or hair cleansing agent, a skin softening agent, fragrance, a dye or a pigment.

[0045] The invention also relates to methods for treating or preventing acne which include applying to the skin a therapeutically or prophylactically effective amount of an anti-acne composition according to the invention. [0046] The invention also relates to a method for treating or preventing acne including applying to the skin a therapeutically or prophylactically effective amount of an anti-acne composition including (i) a polymer of 2-propenal, and (ii) a C_3-io alkanediol. In some embodiments of the method, the C3-10 alkanediol in the composition includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9- nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol. In some specific embodiments the C3-10 alkanediol is selected from the group consisting of 1 ,2- propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol. In some embodiments the C3-ioalkanediol is a 1 ,2-C3-ioalkanediol. The 1 ,2-C_3-ioalkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2- pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2-nonanediol and 1 ,2-decanediol. In some particular cases the 1 ,2-C_3-i₀alkanediol may be selected from the group consisting of 1 ,2- propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

[0047] In some embodiments of the methods of treating and preventing acne of the invention the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

[0048] The present invention also relates to use of (i) a polymer of 2-propenal and (ii) a C3-ioalkanediol in the manufacture of a medicament for treating or preventing acne. In some cases the C3-io alkanediol used in the manufacture of the medicament includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3- propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol. In some specific cases the C-3-ιο alkanediol is selected from the group consisting of 1 ,2- propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol. In some embodiments the polymer of 2-propenal used in the manufacture of the medicament for treating acne is poly(2-propenal, 2-propenoic acid).

[0049] In some embodiments the C3-ioalkanediol used in the manufacture of the medicament for treating or preventing acne is a 1 ,2-C3-ioalkanediol. The 1 ,2-C3- ioalkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2- butanediol, 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2- nonanediol and 1 ,2-decanediol. In some particular cases the 1 ,2-C3-ioalkanediol used in the manufacture of the medicament for treating or preventing acne may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.

[0050] The present invention also relates to an anti-dermatitis composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

[0051] In some embodiments of the anti-dermatitis compositions of the invention the C-3-ιο alkanediol in the composition includes at least one compound selected from the group consisting of 1 ,2-ethanediol, 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3- butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4-pentanediol, 1 ,5- pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6-hexanediol, 2,5- hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9-nonanediol, 1 ,2- decanediol, 1 ,10-decanediol and neopentyl glycol. In some particular embodiments the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

[0052] In some particular embodiments of the anti-dermatitis compositions of the invention the C-3-ιο alkanediol is a 1 ,2-C3-ioalkanediol. In some embodiments, the 1 ,2-C3- i₀alkanediol can be selected from the group consisting of 1 ,2-propanediol, 1 ,2- butanediol, 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2- nonanediol and 1 ,2-decanediol. In some cases the 1 ,2-C3-ioalkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.

[0053] In some embodiments of the anti-dermatitis compositions of the invention, the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

[0054] In some embodiments the anti-dermatitis composition includes from 0.01 to 10 wt% of the polymer of 2-propenal based on the total weight of the composition. In some specific cases the composition includes from 0.05 to 5 wt% of the polymer of 2-propenal.

[0055] The anti-dermatitis compositions of the invention typically include from 0.1 to 99.99 wt% of the C3-ioalkanediol based on the total weight of the composition. In some specific cases the compositions include from 1 to 80 wt% of the C3-ioalkanediol. In other cases the compositions include from 1 to 50 wt% of the C3-ioalkanediol. In some specific embodiments the compositions include from 1 to 20 wt% of the C_3-i₀alkanediol.

[0056] Anti-dermatitis compositions of the invention may further include a

In some specific embodiments, the C2-ioalkanol is selected from the group consisting of ethanol and isopropanol. In some specific embodiments the ratio of the C3-ioalkanediol to the C_2-ioalkanol is between 1 :10 and 10:1 .

[0057] Anti-dermatitis compositions of the invention may further include one or more of a dermatologically acceptable carrier, a stabilizing agent, a thickening agent, a preservative, a skin or hair cleansing agent, a skin softening agent, fragrance, a dye or a pigment.

[0058] The invention also relates to methods for treating or preventing dermatitis which include applying to the skin a therapeutically or prophylactically effective amount of an anti-dermatitis composition according to the invention. [0059] The invention also relates to a method for treating or preventing dermatitis including applying to the skin a therapeutically or prophylactically effective amount of an anti-dermatitis composition including (i) a polymer of 2-propenal, and (ii) a C_3-io alkanediol. In some embodiments of the method, the C-3-ιο alkanediol in the composition includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol. In some specific embodiments the C-3-ιο alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol. In some embodiments the C3-ioalkanediol is a a 1 ,2-C3-ioalkanediol. The 1 ,2-C3-ioalkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2- pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2-nonanediol and 1 ,2- decanediol.ln some specific embodiments the 1 ,2-C_3-i₀alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

[0060] In some embodiments of the methods of treating or preventing dermatitis of the invention the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

[0061] The present invention also relates to the use of (i) a polymer of 2-propenal and (ii) a C3-ioalkanediol in the manufacture of a medicament for treating or preventing dermatitis. In some embodiments the C3-10 alkanediol used in the manufacture of the medicament includes at least one compound selected from the group consisting of 1 ,2- propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3- butanediol, 1 ,2-pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2- hexanediol, 1 ,5-hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2- octanediol, 1 ,8-octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol. In some specific embodiments the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol. In some embodiments the polymer used in the manufacture of a medicament for treating dermatitis is 2-propenal is poly(2-propenal, 2-propenoic acid).

[0062] In some embodiments the C3-ioalkanediol used in the manufacture of the medicament for treating or preventing dermatitis is a 1 ,2-C3-ioalkanediol. The 1 ,2-C3- ioalkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2- butanediol, 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2- nonanediol and 1 ,2-decanediol. In some particular cases the 1 ,2-C3-ioalkanediol used in the manufacture of the medicament for treating or preventing dermatitis may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.

Detailed Description of the Invention

[0063] The term "dermatologically-acceptable," as used herein, means that the components so described are suitable for use in contact with human skin without undue toxicity, incompatibility, instability, allergic response, and the like.

[0064] Compositions of the invention contain a polymer of 2-propenal. Polymers of 2- propenal may have the repeating unit:

wherein R is H.

[0065] Polymers of 2-propenal may also have chemical moieties corresponding to the hydrated, hemiacetal or acetal form of the repeating unit. Other structural units may be formed during or after the polymerization. Polymers of 2-propenal suitable for use with the invention include polymers and copolymers having groups with one or more of the following structures:

wherein X are the remaining portions of the polymer.

[0066] It will, however, be appreciated that because of the option of oxygen-carbon or carbon-carbon polymerization the structure can vary significantly within the polymer. The molecular weight of the polymer is generally at least 1000 such as in the range of from 1000 to 10,000.

[0067] Polymers of 2-propenal suitable for use on the compositions of the invention can be prepared by radical or anionic polymerization of 2-propenal, with or without the addition of co-monomers. In some specific embodiments of the invention the polymer is formed by the anionic polymerization of 2-propenal. In other cases the copolymer suitable for use with the invention may be prepared by reacting a suitable precursor polymer. For instance, a polymer suitable for use with the invention may be synthesized by partial reduction of a precursor such as poly(2-propenoic acid) to form poly(2- propenal, 2-propenoic acid), or by partial oxidation of poly(2-propenal) to form poly(2- propenal, 2-propenoic acid). In some particular embodiments, the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid) formed by the oxidation of poly(2-propenal) to introduce carboxyl groups. In some particular embodiments the poly(2-propenal, 2- propenoic acid) includes from 0.1 to 5 moles of carboxyl groups per kilogram of polymer.

[0068] Compositions of the invention may employ any C3-10 alkanediol. The C3-10 alkanediol may be a linear chain C3-10 alkanediol or a branched chain C-3-ιο alkanediol. The C3-10 alkanediol may be substituted or unsubstituted. As noted above, the C_3-io alkanediol in the composition may be selected from the group consisting of 1 ,2- propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3- butanediol, 1 ,2-pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2- hexanediol, 1 ,5-hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2- octanediol, 1 ,8-octanediol, 1 ,9 nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol. In some cases, C3-10 alkanediol is a 1 ,2-C-3-ioalkanediol. The 1 ,2-C-3-io alkanediol may be a linear chain 1 ,2-C-3-io alkanediol or a branched chain 1 ,2-C3-io alkanediol. The 1 ,2-C3-io alkanediol may be substituted or unsubstituted. In some cases, the 1 ,2-C_3-ioalkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-pentanediol, 1 ,2-hexanediol, 1 ,2-heptanediol, 1 ,2-octanediol, 1 ,2- nonanediol and 1 ,2-decanediol. In some cases the C-3-ιο alkanediol is a 1 ,2-C-3- ioalkanediol selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2- hexanediol and 1 ,2-octanediol.

[0069] The compositions according to the invention can be made up in the customary manner and used for the treatment of one or more of the skin, hair, nails and scalp in the sense of a dermatological treatment or of a treatment in the sense of medicated cosmetics. However, they can also be employed in decorative cosmetics in make-up products. [0070] For use, the compositions according to the invention are applied to one or more of the skin, hair, nails and scalp in adequate amount in the manner customary for cosmetics and dermatological agents.

[0071] The compositions according to the invention can contain cosmetic auxiliaries such as are customarily used in such preparations, e.g. preservatives, bactericides, antioxidants, perfumes, agents for preventing foaming, colorants, pigments which have a colouring action, thickeners, surface-active substances, emulsifiers, emollient substances, moisturizing and/or moisture-retaining substances, fats, oils, waxes or other customary constituents of a cosmetic formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.

[0072] If the composition is a solution or lotion, the dermatologically-acceptable carriers used can be water or aqueous solutions; oils, such as triglycerides of capric or of caprylic acid, or castor oil; fats, waxes and other natural and synthetic fatty materials, preferably esters of fatty acids with alcohols of low C number, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids; alcohols of low C number, and also their ethers, preferably ethanol, isopropanol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products. In some cases, mixtures of the abovementioned solvents are used. In the case of alcoholic solvents, water can be a further constituent.

[0073] Some specific examples of dermatologically-acceptable carriers suitable for application with the invention include water, olive oil, peanut oil, sesame oil, sunflower oil, safflower oil, arachis oil, coconut oil, liquid paraffin, polyethyleneglycol, ethanol, propanol, isopropanol, glycerol, fatty alcohols, triglycerides, polyvinyl alcohol, partially hydrolysed polyvinyl acetate). Other suitable carriers would be appreciated by one having ordinary skill in the art. [0074] Various embodiments of the compositions of the invention may include a stabilizing agent. The stabilizing agent may be an antioxidant selected from the group consisting of amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D,L- carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. a-carotene, β-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (e.g. dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulphoximine compounds (e.g. buthionine sulphoximines, homocysteine sulphoximine, buthionine sulphones, penta-, hexa- or heptathioninesulphoxime) in very low tolerable doses (e.g. pmol to μηηοΙ/kg), further (metal) chelators (e.g. a-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), a- hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g. γ-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (e.g. ascorbyl palmitate, Mg-ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate from benzoin, rutic acid and its derivatives, ferulic acid and its derivatives, butylhydroxytoluene, butylhydroxyanisole, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (e.g. ZnO, ZnS0 ), selenium and its derivatives (e.g. selenomethionine), stilbenes and their derivatives (e.g. stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these said active compounds. The stabilizing agent may be present at a concentration of from 0.01 -3.0%. [0075] The compositions of the present invention can also include a thickening agent. Suitable thickening agents include cellulose and derivatives thereof such as carboxymethylcellulose, hydroxyethylcellulose, cellulose acetate propionate carboxylate, hydroxyethylcellulose, hydroxyethyl ethylcellulose, hydroxypropylcellulose, hydroxypropyl methylcellulose, methyl hydroxyethylcellulose, microcrystalline cellulose, sodium cellulose sulfate, and mixtures thereof. Further suitable thickening agents include alkyl substituted celluloses. In these polymers the a proportion of the hydroxy groups of the cellulose polymer are hydroxyalkylated (preferably hydroxyethylated or hydroxypropylated) to form a hydroxyalkylated cellulose which is then further modified with a C10-C30 straight chain or branched chain alkyl group through an ether linkage. Typically these polymers are ethers of Cio-C₃₀ straight or branched chain alcohols with hydroxyalkylcelluloses. Examples of alkyl groups useful for modifying the hydroxyalkyl cellulose include those selected from the group consisting of stearyl, isostearyl, lauryl, myristyl, cetyl, isocetyl, cocoyl (i.e. alkyl groups derived from the alcohols of coconut oil), palmityl, oleyl, linoleyl, linolenyl, ricinoleyl, behenyl, and mixtures thereof.

[0076] Other thickening agents suitable for use with the compositions of the invention include acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar hydroxypropyltrimonium chloride, hectorite, hyaluronic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboxymethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.

[0077] Compositions according to the invention may further include preservatives. Suitable preservatives include, but are not limited to, Ci-C₄ alkyl parabens and phenoxyethanol, calcium propionate, sodium nitrate, sodium nitrite, sulfites (sulfur dioxide, sodium bisulfite, potassium hydrogen sulfite, etc.) and disodium EDTA. Preservatives are typically present in an amount ranging from about 0.01 % to about 2.0% by weight percent, based on the total composition. [0078] The compositions of the invention optionally include a skin or hair cleansing agent. The skin or hair cleansing agent may take the form of a soap or surfactant. Examples of anionic surfactants potentially useful in the compositions of the invention include, but are not limited to, soaps, sulfates, sulfonates and carboxylates such as alkyl carboxylate salts. More specifically, useful anionic surfactants include alkyl sulfates and sulfonates, alkyl ether sulfates and sulfonates, alkyl aryl sulfates and sulfonates, aryl sulfates and sulfonates, sulfated fatty acid esters, sulfonated fatty acids, sulfated monoglycerides, sulfonated olefins, primary or secondary alkane sulfonates, alkyl sulfosuccinates, acyl taurates, methyl acyl taurates, acyl isothionates, alkyl glyceryl ether sulfonates, sulfonated methyl esters, alkyl phosphates, acyl glutamates, acyl sarcosinates, alkyl sulfoacetates, acylated peptides, alkyl ether carboxylates, acyl lactylates, anionic fluorosurfactants, ethoxylated alkyl sulfates, alkyl glyceryl ether sulfonates, fatty acyl glycinates, a-sulfonated fatty acids, their salts and/or their esters, alkyl ethoxy carboxylates, and mixtures thereof.

[0079] Any counter cation can be used in the anionic surfactant. In some specific cases the counter cation is selected from the group consisting of sodium, potassium, and counter cations derived from diethanolamine, or triethanolamine. In some particular embodiments the counter cation is sodium or potassium.

[0080] One group of anionic surfactants which may be used in the compositions of the invention is the group consisting of disodiumdecyl(sulfoxy)benzene sulphonate, sodium lauryl sulfate and disodium oxybis(decylsulfophenoxy)benzene sulfonate.

[0081] When the composition is in the form of a skin cleaner the composition may include a soap. A soap is a surfactant having neutral to alkaline pH typically derived by neutralization of fatty acids with alkaline compounds such as alkali metal hydroxide or alkanolamines. [0082] Examples of non-ionic surfactants potentially suitable for use with the compositions of the invention include, but are not limited to, alkyl polyglycosides, alcohol ethoxylates such as fatty alcohol ethoxylates and/or propoxylates, alkyl phenolethoxylates, glycol ester surfactants, PEG(20) sorbitan monooleate, polyethylene glycol cocoate, propylene oxide/ethylene oxide block polymers, alkanolamines, and mixtures thereof.

[0083] Some specific non-ionic surfactants suitable for use in the compositions of the invention include polyoxyalkylene glycol based surfactants. These polyoxyalkylene based surfactants include hexitan esters such as polysorbates, polyethoxylated alkylphenols, poloxamers, polyethoxylated fatty alcohols, polyoxyethylene glycol monoethers, alkyl polyglucosides and ethoxylated polysiloxanes.

[0084] Examples of amphoteric surfactants useful in compositions of the invention include but are not limited to betaines, amine oxides, sultaines, and mixtures thereof. More specifically, examples of useful amphoteric surfactants include alkyl betaines (oleyl betaine and lauryl betaine), cocamidopropyldimethyl betaine, cocamido betaine, alkyl sultaines, alkyl amphoacetates (cocamphoacetate), alkyl amphodiacetates (cocamphodiacetate), alkyl amphopropionates, alkyl amphodipropionates (cocamphocarboxypropionate), cocamphocarboxy propionic acid, cocamidopropylhydroxysultaine, alkyldimethyl amine oxides, coconut monoethanolamine, cetyldimethylamine oxide, stearamine oxide, oleamine oxide, cocamidopropylamine dimethyl oxide, and mixtures thereof.

[0085] Other skin or hair cleansing agents appropriate for use in the compositions of the invention would be readily known by one of ordinary skill in the art.

[0086] The compositions of the invention may also include a skin softening agent. The skin softening agents suitable for use with the compositions of the invention are, when incorporated into the composition and applied to the skin, essentially clear, colorless, and non-malodorous. They are dermatologically safe and are compatible with the active agents of the compositions as well as any other composition ingredients. The skin softening agents can be used singly or in combination in a concentration ranging from approximately 0.01 to 10.0% w/v. In some embodiments they are included in the range of from approximately 0.05 to 5.0%. Skin softening agents suitable for use in the present invention include, but are not limited to, glycerin, caprylic/capric triglyceride, pantothenol and its derivatives and related moieties, and hyaluronic acid and related moieties. Other appropriate skin softening agents suitable for use in the compositions of the invention would be readily known to one having ordinary skill in the art.

[0087] The compositions according to the invention may also include a fragrance. The fragrance may be present at between about 0.0001 % (v/v) and about 2.0%) (v/v) of the final composition. In some cases the fragrance is present between about 0.001 % (v/v) and 1 .0% (v/v). In still other cases the fragrance is present between 0.01 % (v/v) and 5% (v/v) of the final composition. For the purpose of the present application the term "fragrance" is meant to encompass any component reacting with the human olfactory sites and imparting a pleasurable odor, essence or scent. Fragrances that may be used in accordance with the present invention include any synthetic as well as natural fragrance and mixtures thereof. Typically a multiplicity of fragrances are used to achieve the desired effect. Those of skill in the art further recognize the terms "top note" (i.e. fragrances having a high vapor pressure), "middle note" (i.e. fragrance having a medium vapor pressure) and "base note" (i.e. fragrances having a low vapor pressure). Recognizing that categorization within these classes may depend to some extent on the fragrance formulator, the compositions of the present invention may include any top note, middle note and base note fragrance. A further way of classifying fragrances is in accordance with generally recognized scents they produce. Descriptors used by those skilled in the art of fragrances are, inter alia, "rose", "floral", "green", "citrus", "spicy", "honey", "musk", "herbal, "jasmine", "lilac", lily of the valley", "orange", "peach", "oriental", "watermelon" "chypre" and "lemon", "woody", "fruity" all of which fragrances thus classified may be formulated with the compositions of the present invention. [0088] Fragrances that may be used in accordance with the present invention include linear and cyclic alkenes (i.e. terpenes); primary, secondary and tertiary alcohols; ethers; esters; ketones; nitrites; and saturated and unsaturated aldehydes; or mixtures thereof.

[0089] Examples of synthetic fragrances that may be used in the compositions of the present invention include acetanisole, acetophenone, acetyl cedrene, methyl nonyl acetaldehyde, musk anbrette, heliotropin, citronellol, sandella, methoxycitranellal, hydroxycitranella), phenyl ethyl acetate, phenyletlhylisobutarate, gamma methyl ionone, geraniol, anetlhole, benzaldehyde, benzyl acetate, benzyl salicate, linalool, ciitiamic alcohol, phenyl acetaldehyde, amyl cinnamic aldehyde, caphore, p-tertiary butyl cyclohexyl acetate, citral, cinnamyl acetate, citral diethyl acetal, coumarin, ethylene brasslate, eugenol, 1 -menthol, vanillin, and mixtures thereof. It will of course be appreciated that other dermatologically acceptable synthetic fragrances suitable for use in the compositions of the invention would be readily known to one having ordinary skill in the art.

[0090] Examples of natural fragrances that may be used in the compositions of the present invention include without limitation lavandin, heliotropin, sandlewood oil, oak moss, pathouly, ambergris tincture, ambrette seed absolute, angelic root oil, bergamont oil, benzoin Siam resin, buchu leaf oil, cassia oil, cedarwood oil, cassia oil, castorcum, civet absolute, chamomile oil, geranium oil, lemon oil, lavender oil, Ylang Ylang oil, and mixtures thereof. It will of course be appreciated that other dermatologically acceptable natural fragrances suitable for use in the compositions of the invention would be readily known to one having ordinary skill in the art.

[0091] Compositions of the invention may also include a dye. Dyes suitable for use with the compositions of the invention include fat-soluble dyes and water-soluble dyes. The dye, if present, may be present in an amount generally ranging from 0.001 % to 2.0% by weight relative to the total weight of the composition. In some cases the dye is present in an amount from 0.005% to 1.0%. In other cases the dye is present in an amount from 0.01 % to 0.5%. As will be appreciated by one having skill in the art, dyes suitable for use with the compositions of the invention will be dermatologically acceptable dyes.

[0092] Examples of fat-soluble dyes include Soudan red, D & C Red 17, D & C Green 6, β-carotene, soybean oil, Soudan brown, D & C Yellow 1 1 , D & C Violet 2, D & C Orange 5, and quinoline yellow. Examples of water-soluble dyes include beet juice and methylene blue.

[0093] Compositions of the invention may also include a pigment. The pigment can be white or colored, inorganic and/or organic, coated or uncoated. Suitable such inorganic pigments include titanium dioxide, optionally treated on its surface, or zirconium oxide or cerium oxide, as well as iron oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue. Suitable organic pigments include carbon black, and lakes based on cochineal carmine or on barium, strontium, calcium or aluminum.

[0094] In some cases the pigments may be pearlescent. The pearlescent pigments can be selected from white pearlescent pigments such as mica covered with titanium oxide or with bismuth oxychloride, colored pearlescent pigments such as titanium oxide-coated mica coated with iron oxides, titanium oxide-coated mica coated with, in particular, ferric blue or chromium oxide, or titanium oxide-coated mica coated with an organic pigment of the above-mentioned type, as well as pearlescent pigments based on bismuth oxychloride.

[0095] Compositions of the invention may be formulated as any type of formulation appropriate for application to the skin or hair. In some cases the compositions of the invention may be formulated as a lotion, a hand lotion, a sunscreen, a cream, a face cream, a hand cream, a moisturizer, a barrier cream, a hand sanitizer, a soap, a hair lotion, a hair gel, a hair mousse, a shaving cream, a shaving gel, a deodorant, a night emollient cream, a hair treatment course, a hair rinse, a hair spray, a shampoo, a conditioner, a lipstick, a formulation for blow-drying, a formulation for hair setting, a formulation for colouring or bleaching, a styling or treatment lotion, a hair lacquer, or a permanent wave composition.

[0096] For the methods of the invention, the compositions according to the invention are applied to the skin and/or the hair in adequate amounts in the manner customary for cosmetics and dermatological agents. The precise amount applied will be dependent on the precise formulation adopted and on the severity of the complaint for which the composition is being applied.

[0097] The compositions may be applied to skin or hair while wet or while dry. In some cases, the compositions will be rinsed from the skin or hair immediately after applying, as in a process of washing the hair or skin. In other cases the compositions may be applied and left in contact with the skin for a variable period of time, after which the composition is removed. In still other cases, the compositions may be rubbed onto or into the skin or hair and left, as in application a hand cream or certain leave-in hair conditioners.

[0098] In some instances the methods of the invention will be applied in association with other treatments or methods. For instance, when the methods of the invention involve the application of a composition formulated as a shampoo, this might be applied in association with an appropriate conditioner. In other cases, the methods of the invention might involve the application of compositions of the invention as a conditioner in association with an appropriate shampoo. In some cases the compositions of the invention may be applied as formulations used while rinsing the hair before or after shampooing, before or after permanent wave treatment, or before or after colouring or bleaching the hair.

[0099] In addition to the conditions included above, compositions according to the invention may also be useful in the treatment of rosacea, dermaphytoses, impetigo, folliculitis, furunculosis, ecthyma, eczema, psoriasis, herpes, epidermolysis bullosa and icthyosis. Compositions according to the invention may also be useful for preventing or treating infection of traumatic lesions (such as ulcers, minor burns, cuts, abrasions, lacerations, wounds, biopsy sites, surgical incisions and insect bites).

[0100] Examples of materials and methods for use with the compositions and methods of the present invention will now be provided. In providing these examples, it is to be understood that the specific nature of the following description is not to limit the generality of the above description.

EXAMPLES

[0101] Poly(2-propenal, 2-propenoic acid) was used in powdered form obtained by the following method. Water (720 mL at ambient temperature, about 20°C) and 2-propenal (60g; freshly distilled) were placed in an open beaker, within a fume cupboard and vigorously stirred. Then, 0.2M aqueous sodium hydroxide (21 .4 mL) was added to bring the pH to 10.5 - 1 1 .0. Within a minute, the clear solution became milky and then precipitation of a white flocculant polymer began, and appeared complete within 30 minutes. The precipitate was filtered and washed with water (250 mL), dried at room temperature (2 days) to yield 25g of white polypropenal. The polymer was spread on trays and heated in a temperature controlled oven at 40°C/8 hours. This heating was continued at the schedules : 50°c/15 hours; 65°C/4 hours/75°C/18 hours; 84°C/24 hours.

[0102] Poly(2-propenal, 2-propenoic acid) was also prepared by preparing polypropenal as above, but alternatively dissolving the polymer (10g) as a 10% solution in ethanol, adding 30% w/w hydrogen peroxide (4.5 mL). The solution was heated at 75°C for 2 hours. The ethanol was evaporated and the product dried to give a white semi- crystalline product.

[0103] Poly(2-propenal, 2-propenoic acid) produced by either oxidation method have identical physicochemical and antimicrobial properties.

[0104] The compositions of Examples 1 to 32 and 37 to 50 may be prepared by mixing the poly(2-propenal, 2-propenoic acid) with the alcohol portions with mild heating to no more than 70°C if necessary to dissolve the polymer. Once dissolved, the remaining components are mixed with the solution to provide a homogenous composition. Example 1 - Hair Lotion Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- propanediol

Example 2 - Hair Lotion Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol

Example 3 - Hair Lotion Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- pentanediol

Example 4 - Hair Lotion Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- hexanediol

Example 5 - Hair Lotion Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- heptanediol

Example 6 - Hair Lotion Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- octanediol

Example 7 - Hair Lotion Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- nonanediol

Example 8 - Hair Lotion Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- decanediol

Example 9 - Hair Treatment Course Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2-propanediol

Example 10 - Hair Treatment Course Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,3-butanediol

Example 11 - Hair Treatment Course Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2-pentanediol

Example 12 - Hair Treatment Course Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2-hexanediol

Example 13 - Hair Treatment Course Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2-heptanediol

Example 14 - Hair Treatment Course Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2-octanediol

Example 15 - Hair Treatment Course Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2-nonanediol

Example 16 - Hair Treatment Course Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2-decanediol

Example 17 - Hair Rinse Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- propanediol

Example 18 - Hair Rinse Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- butanediol

Example 19 - Hair Rinse Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- pentanediol

Example 20 - Hair Rinse Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- hexanediol

Example 21 - Hair Rinse Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- heptanediol

Example 22 - Hair Rinse Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- octanediol

Example 23 - Hair Rinse Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- nonanediol

Example 24 - Hair Rinse Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- decanediol

Example 25 - Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- propanediol

Example 26 - Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- butanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Total 100 100 100 100

Example 27 - Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- pentanediol

Example 28 - Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- hexanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Pearlescent agent 4.0 4.0 4.0 4.0

Preservatives,

fragrance, dye, 1 .0 1 .0 1 .0 1.0 thickeners

Water 76.25 74.3 75.45 73.5

Total 100 100 100 100

Example 29 - Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- heptanediol

Example 30 - Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- octanediol

Example 31 - Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- nonanediol

Component % (w/w) % (w/w) % (w/w) % (w/w)

Total 100 100 100 100

Example 32 - Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- decanediol

Example 33 - Antimicrobial Activity of Compositions of the Invention

[0105] Samples were prepared by adding selected C_3-ioalkanediols to a final concentration of either 2000 or 10000 ppm in an ethanolic solution of poly(2-propenal, 2- propenoic acid) (2000 ppm). Compositions studied are tabulated in Table 1 . Table 1 : Composition of C_3-ioalkanediol / poly(2-propenal, 2-propenoic acid) [PPPA] Antimicrobial Compositions (Concentrations are ppm in ethanol)

[0106] The minimum inhibitory concentration (MIC) of poly(2-propenal, 2-propenoic acid) was thereafter determined against Escherichia coli (ATCC 8739 strain) after evaporation of the ethanol. The MIC values determined are tabulated in Table 2.

Table 2: Minimum Inhibitory Concentration Results for Examples 1-9

[0107] It is evident that the minimum inhibitory concentration determined in the presence of a C3-ioalkanediol is substantially lower than that determined with the poly(2-propenal, 2-propenoic acid). Moreover there is a substantial improvement relative to the minimum inhibitory concentration of 1 ,2-hexanediol and 1 ,2-octanediol against E.coli (These have previously been reported to be 10,000 ppm and 6,300 ppm, respectively.) The improved MIC is also observed throughout the series of C3-ioalkanediols, rather than being more evident with C_6-ioalkanediols. These results indicate the synergistic antimicrobial activity of compositions according to the invention.

EXAMPLES 34 - 36

Placebo controlled Study

Trial with active at 500 ppm, 1000 ppm and 2000 ppm

[0108] The purpose of this placebo controlled study is to evaluate the efficacy of an anti- dandruff treatment when tested over a 16 days period. Efficacy was evaluated for each subject through analysis of debris collection via D-Squame surface sampling discs. In addition the efficacy and tolerance were evaluated using panelist self-assessment via questionnaire responses.

Sample Description

[0109] A control placebo was prepared by combining the following components in the amounts by weight specified.

Component Weight %

Propylene glycol 10%

Ethanol 40%

Water to 100%

[0110] Corresponding compositions of Examples 34 to 36 which were used in the three arms of the study, were prepared by dissolving poly(2-propenal, 2-propenoic acid) ("PPPA") in powdered form in the alcohol component and mixing the alcohol solution with water to provide a homogenous solution.

Example No. Concentration of PPPA

Control 0 ppm

Example 34 500 ppm

Example 35 1000 ppm

Example 36 2000 ppm

Test Material Evaluation Prerequisite

[0111] Prior to induction of a human test panel, toxicology, microbiology or in-vitro performance spectra may be required to assess the feasibility of commencement as dictated by an Institutional Review Board (IRB) described in Section 4.4.

Test Material Handling

[0112] Upon arrival at the testing laboratory, the test materials were assigned unique laboratory code numbers and entered into a daily log identifying the lot number, sample description, sponsor, date received and tests requested.

Population Demographics

Number of subjected enrolled in each arm of the study 6

Number of subjects completing study 6

Age Range 32 - 71

Sex Male 4

Female 2

Race Caucasian 6

[0113] Subjects with a history of any form of skin cancer, melanoma, lupus, connective tissue disease, diabetes or any disease that would increase risk associated with study participation. [0114] Individuals diagnosed with chronic skin allergies or with history of hypersensitivity to cosmetics in general.

Methodology

[0115] Six healthy subjects (males and females) between the ages of 32 and 71 were inducted into this study. The subjects were pre-qualified for participation based on restrictions described in the inclusion/exclusion criteria in Section 4.1 and 4.2. In order to pre-condition the test sites and keep all treatments consistent during the study, the panelists were required to use only a baby shampoo product for a period of 7 days prior to study commencement and to use only the assigned test material throughout the study period.

Study Design:

Day 1 : Scalp debris collection (Baseline)

Day 1-7: 7 day use with Placebo

Day 8: Scalp debris collection post Placebo

Day 8-15: 7 day use with active

Day 16: Scalp debris collection post active

[0116] All participants were instructed to apply test materials according to the following sponsor supplied directions:

Shampoo your hair using normal (not anti-dandruff) shampoo. Towel dry and then apply sufficient amount of the test product (about 5-7ml) to the scalp and massage in well. Use as a leave-on product once a day.

[0117] Participants were provided with a daily log and instructed to record the time of each application together with any subjective comments regarding product usage. Scalp debris collection via D-Squame surface sampling (described below) at fixed anatomical locations was employed prior to the initial application, after 8 days of the first application of control Placebo and again after 8 days of the first application of Example composition. [0118] In addition, participants were asked to fill out a self-assessment questionnaire prior to the initial application of Placebo + Active and again after 7 days of treatment.

D-SQUAME Skin Sampling Discs

[0119] Adhesive discs take the trial and error out of sampling the cells of the superficial stratum corneum (top layer of skin). These crystal clear discs provide the required rigidity and adhesion to uniformly sample a fixed area of skin surface. The clear polymer discs provide optimum visibility of adhering skin cells and allow staining by many histological preparations.

[0120] D-Squame disc is applied to clean, dry skin surface. It is pressed firmly for a few seconds using thumb or fingertips, and then transferred to a black square on the storage card where is compared with reference patterns. Heavy amount of scaling represents pattern 5. Normal skin producing a few areas of small clumps of cells or a fine even single layer of cells represents pattern 1 .

Statistical Source Data

[0121] The source data are collected Questionnaire responses and D-Squame Skin Sampling Discs employed prior to application (Baseline) and again after 8 (Post Treatment - Placebo) and 16 days following the applications of the Example materials. The data used in the statistical analysis reflect changes from Baseline and Post Treatment - Placebo evaluation.

[0122] D-SQUAME Skin Sampling Discs method describes pattern representing 100% improvement in the condition (no scaliness) as 1 , therefore the following formula was used to calculate the reduction in scal flakiness:

where: x = Baseline (Day 1 ) - D-Squame Skin Sampling Discs test mean results y = Post Treatment - Placebo (Day 8) D-Squame Skin Sampling Discs test mean results z = 1 - minimum D-Squame Skin Sampling Discs value (100% reduction)

or

x = Post Treatment - Placebo (Day 8) D-Squame Skin Sampling Discs test mean results y = Post Treatment - Active (Day 16) D-Squame Skin Sampling Discs test mean results z = 1 - minimum D-Squame Skin Sampling Discs value (100% reduction)

Results

[0123] The results are shown in the following tables and the attached drawings:

Example 34 Table 3 & 4 Fig. 1

Example 35 Table 5 & 6 Fig. 2

Example 36 Table 7 & 8 Fig. 3

In the drawings:

Figure 1 is a column chart comparing the flake reduction via D-Squame score for the 500ppm composition of Example 34 sixteen days post treatment with a placebo.

Figure 2 is a column chart comparing the flake reduction via D-Squame score for l OOOppm composition of Example 35 sixteen days post treatment with a placebo.

Figure 3 is a column chart comparing the flake reduction via D-Squame score for the 2000ppm composition of Example 36 sixteen days post treatment with a placebo.

Observations

[0124] No adverse effects or unexpected reactions of any kind were observed on any of the subjects. Conclusions:

[0125] Within the limits imposed by the conduct and population size of the study described herein, the anti-dandruff test treatment with poly(2-propenal, 2-propenoic acid) demonstrated dramatic reduction in mean flakiness of scalp after 7 days use (Day 16). Observed differences in surface scaling of the site of the head treated with the test regimen are considered statistically significant with a maximum reduction observed on Day 16 of the study.

[0126] Subjective questionnaire responses corroborated the skin surface sampling data. Throughout the test period, the majority of test panelists perceived the test product to be an effective anti-dandruff product and that it reduced the conditions associated with dandruff.

Table 3

^*Statistically Significant

The flake reduction via D-Squame score (mean score) of the Example 34 composition - (500ppm) compared with the placebo, is shown as a column chart in Figure 1. Product Questionnaire Summary

[0127] Intensity of perceived dandruff related condition was ranked in the following scale:

0 None

1 Barely

2 - 3 Slightly

4 - 5 Definitely

6 - 7 Moderately

8 - 9 Dramatically

10 The Most Intense Imaginable

Table 4

Visual Dandruff Grading Summary via D-Squame Score

Table 5

*Statistically Significant

The flake reduction via D-Squame score (mean score) of the Example 35 composition - (l OOOppm) compared with the placebo, is shown as a column chart in Figure 2.

Product Questionnaire Summary

[0128] Intensity of perceived dandruff related condition was assessed in the following scale:

0 None

1 Barely

2 - 3 Slightly

4 - 5 Definitely

6 - 7 Moderately

8 - 9 Dramatically

10 The Most Intense Imaginable Table 6

Visual Dandruff Grading Summary via D-Squame Score

Table 7

^*Statistically Significant

The flake reduction via D-Squame score (mean score) of the Example 36 composition -

(2000ppm) compared with the placebo, is shown as a column chart in Figure 3. Product Questionnaire Summary

[0129] Intensity of perceived dandruff related condition was assessed in the following scale:

0 None

1 Barely

2 - 3 Slightly

4 - 5 Definitely

6 - 7 Moderately

8 - 9 Dramatically

10 The Most Intense Imaginable

Table 8

FURTHER FORUMLATIONS

Example 37 - Hair Rinse Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol

Example 38 - Shampoo Formulation: Poly(2-propenal, 2-propenoic acid) and 1 ,3- butanediol

Example 39 - Skin Cleansing Formulations

Example 40: Hair Care Cleansing Formulations

Water + Silicone Quaternium-18 +

5 3 Trideceth-6 + Trideceth-12

Dimethicone + Cocamidopropyl Betaine +

C12-15 Pareth-3 + Guar 1 1 Hydroxypropyltrimonium Chloride

Example 42: Hair Conditioner Formulations

Example 43: Water in Oil Emulsion Formulations

Example 44: Hydrodispersion Formulations

Example 45: Silicon in Water Emulsion Formulations

Component % (w/w) % (w/w)

Bis-PEG/PPG-16/16 PEG/PPG16/16

2 8 Dimethicone, Caprylic/Caprictriglycerid

Cyclomethicone 15 25

Dimethicone 15 5

Silicon Elastomer Gel 10

Octyldodecanol 0.75

Glycerol 7.5 15

Panthenol 1 0.75

Perfume 0.4 0.3 Poly(2-propenal, 2-propenoic acid) 0.25 0.1

N-Lauryl-L-Arginine Thyl Ester

Monochloride

Benzethoniumchloride 0.6

Methylpropanediol 3.00

Phenoxyethanol

Trisodium EDTA (aq) 0.20 0.20

Ethylhexylglycerol 0.5

Modified starch 2.5

Water ad 100 ad 100

Example 46: Oil in Water Formulations

Propylenglycol 10

Water ad 100 ad 100

Example 47: Styling Gel Formulations

Example 48: Hairspray Aerosol Formulations

Example 49: Oil in Water SPF 15 Formulations

Benzethoniumchloride 0.5

1 ,2-Pentadiol 0.5

Glyceryl Stearate 1.2 1

Stearic Acid 2.5 3

Polyglyceryl-3

Methylglucose 2 2.5

Di stearate

Glyceryl Stearate

2 1.75 2.5 2.5 Citrate

Sodium Stearoyl

0.2

Glutamate

Sucrose Polystearate

+ Hydrogenated 1

Polyisobutene

ad ad ad ad ad ad ad ad ad

Water

100 100 100 100 100 100 100 100 100

Cera Microcristallina

+ Paraffinum 2 1.5

Liquidum

Glycerol 4 8 4 10 10 8 6 2 12

Cetyl Alcohol 1.25 1 1 1 3 2 4 4

Dimethicone 2 1 4

Cyclomethicone 6 4

Hydrogenated Coco-

1 1 3 4 2 2 Glycerides

Simmondsia

1.5 4

Chinensis Oil

C12-15 Alkyl

1 3

Benzoate

Dicaprylyl Carbonate 3 2 5 6

Caprylic/Capric

2 2.7 2.5 3 3 Triglyceride

Cyclomethicone +

5

Dimethiconol

Dicaprylyl Ether 1

Ethylhexyl Cocoate 5 4 6 6 Tridecyl Stearate +

Tridecyl Trimellitate +

Dipentaerythrityl 2 2 1.5 1 .5 Hexacaprylate/Hexac

aprate

Butyrospermum Parkii

2 2.5 2.5 Butter

Lanolin Alcohol

0.1 0.2 0.1 0.1 (Eucerit®)

Stearyl Alcohol 1 .25 1 3 4 3.5 3.5

Carbomer 0.1 0.075 0.1 0.15 0.2 0.4 0.35 0.45 0.45

Acrylates/C 10-30

Alkyl Acrylate 0.2

Crosspolymer

Chondrus Crispus 0.7

Sodium Hydroxide aq

q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. q.s. 45%

Ethylhexylglycerol 0.5 0.25 0.5 0.25 1 1

Talc 3 4

Ammonium

Acryloyldimethyltaurat 1.5

e/VP Copolymer

EDTA 0.2 0.2 0.1 0.2 0.2

Macadamia Ternifolia 1 0.75 1.3 1 .3

Sodium Polystyrene

0.3 0.4

Sulfonate

Ethylhexyl

Methoxycinnamate + 3 4 9 9

BHT

Ethylhexyl Salicylate 2 4 3

Butyl

Methoxydibenzoylmet 2 2 1 1.5 5

hane

2-(4'-Diethylamino-2'- hydoxy benzoyl )-

1 5

benzoesaurehexylest

er

Titanium Dioxide +

Alumina + 0.45 4

Simethicone Titanium Dioxide 2

Ethylhexyl Triazin 3 1

Bis-

Ethylhexyloxyphenol 0.5 Methoxyphenyltriazin

Octocrylene 5 5

Example 50: SPF>15 Formulations

Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine 1 .50 1 .50

Butyl Methoxydibenzoylmethane 4.50 4.50

Diethylhexyl Butamido Triazone 1 .00 1.00

Titanium Dioxide + Trimethoxycaprylylsilane 3.00 5.00

Claims

CLAIMS:

1 . A topical antimicrobial composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

2. A topical antimicrobial according to claim 1 , wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3- propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol.

3. A topical antimicrobial composition according to any one of claims 1 to 3, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3- butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

4. A topical antimicrobial composition according to any one of claims 1 to 3 wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

5. A topical antimicrobial composition according to any one of claims 1 to 4, wherein the composition includes from 0.01 to 10 wt%, preferably from 0.05 to 5 wt%, of the polymer of 2-propenal based on the total weight of the composition.

6. A topical antimicrobial composition according to any one of claims 1 to 6, wherein the composition includes from 0.1 to 99.99 wt%, preferably from 1 to 80 wt%, more preferably 1 to 50 wt% and even more preferably from 1 to 20 wt%, of the C₃-ioalkanediol based on the total weight of the composition.

7. A topical antimicrobial composition according to any one of claims 1 to 7, further including a C₂-ioalkanol, preferably selected from the group consisting of ethanol and isopropanol.

8. A topical antimicrobial composition according to claim 7, wherein the ratio of the C₃-ioalkanediol to the C₂-ioalkanol is between 1 :10 and 10:1 .

9. A topical antimicrobial composition according to any one of claims 1 to 8, further including one or more of a dermatologically acceptable carrier, a stabilizing agent, a thickening agent, a preservative, a skin or hair cleansing agent, a skin softening agent, a fragrance, a dye or a pigment.

10. A method for inhibiting the proliferation of microbes on the skin including applying to the skin an inhibitory-effective amount of a topical microbial composition according to any one of claims 1 to 9.

1 1 . A method for inhibiting the proliferation of microbes on the skin including applying to the skin an inhibitory-effective amount of a topical antimicrobial composition including (i) a polymer of 2-propenal, and (ii) a C₃-io alkanediol.

12. A method according to claim 1 1 , wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9- nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol.

13. A method according to claim 1 1 or claim 12, wherein the C_3-i₀ alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

14. A method according to any one of claims 1 1 to 13, wherein the polymer of 2- propenal is poly(2-propenal, 2-propenoic acid).

15. Use of (i) a polymer of 2-propenal and (ii) a C₃-ioalkanediol in the manufacture of a topical medicament for inhibiting the proliferation of microbes on skin.

16. Use according to claim 17, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9- nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol.

17. Use according to claim 16 or claim 17, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.

18. Use according to any one of claims 15 to 17, wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

19. An anti-dandruff composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

20. An anti-dandruff composition according to claim 19, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol.

21 . An anti-dandruff composition according to claim 19 or claim 20, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2- hexanediol and 1 ,2-octanediol.

22. An anti-dandruff composition according to any one of claims 19 to 21 wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

23. An anti-dandruff composition according to any one of claims 19 to 22, wherein the composition includes from 0.01 to 10 wt%, preferably from 0.05 to 5 wt%, of the polymer of 2-propenal based on the total weight of the composition.

24. An anti-dandruff composition according to any one of claims 19 to 23, wherein the composition includes from 0.1 to 99.99 wt%, preferably from 1 to 80 wt%, more preferably 1 to 50 wt% and even more preferably from 1 to 20 wt%, of the C₃--ioalkanediol based on the total weight of the composition.

25. An anti-dandruff composition according to any one of claims 19 to 24, further including a C₂--ioalkanol, preferably selected from the group consisting of ethanol and isopropanol.

26. An anti-dandruff composition according to claim 25, wherein the ratio of the C₃. -_loalkanediol to the C₂--ioalkanol is between 1 :10 and 10:1 .

27. An anti-dandruff composition according to any one of claims 17 to 26, further including one or more of a dermatologically acceptable carrier, a stabilizing agent, a thickening agent, a preservative, a skin or hair cleansing agent, a skin softening agent, a fragrance, a dye or a pigment.

28. A method for treating or preventing dandruff including applying to the scalp a therapeutically or prophylactically effective amount of an anti-dandruff composition according to any one of claims 17 to 27.

29. A method for treating or preventing dandruff including applying to the scalp a therapeutically or prophylactically effective amount of an anti-dandruff composition including including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

30. A method according to claim 29, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9 nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol.

31 . A method according to claim 29 or claim 30, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

32. A method according to any one of claims 29 to 31 , wherein the polymer of 2- propenal is poly(2-propenal, 2-propenoic acid).

33. Use of (i) a polymer of 2-propenal and (ii) a C₃-ioalkanediol in the manufacture of a medicament for treating or preventing dandruff.

34. Use according to claim 33, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9 nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol.

35. Use according to claim 33 or claim 34, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.

36. Use according to any one of claims 33 to 35, wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

37. An anti-acne composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

38. An anti-acne composition according to claim 37, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol.

39. An anti-acne composition according to claim 37 or claim 38, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2- hexanediol and 1 ,2-octanediol.

40. An anti-acne composition according to any one of claims 37 to 39, wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

41 . An anti-acne composition according to any one of claims 37 to 40, wherein the composition includes from 0.01 to 10 wt%, preferably from 0.05 to 5 wt%, of the polymer of 2-propenal based on the total weight of the composition.

42. An anti-acne composition according to any one of claims 37 to 41 , wherein the composition includes from 0.1 to 99.99 wt%, preferably from 1 to 80 wt%, more preferably 1 to 50 wt% and even more preferably from 1 to 20 wt%, of the C₃--ioalkanediol based on the total weight of the composition.

43. An anti-acne composition according to any one of claims 37 to 42, further including a C₂--ioalkanol, preferably selected from the group consisting of ethanol and isopropanol.

44. An anti-acne composition according to claim 43, wherein the ratio of the C₃- -_loalkanediol to the C₂-ioalkanol is between 1 :10 and 10:1 .

45. An anti-acne composition according to any one of claims 37 to 44, further including one or more of a dermatologically acceptable carrier, a stabilizing agent, a thickening agent, a preservative, a skin or hair cleansing agent, a skin softening agent, a fragrance, a dye or a pigment.

46. A method for treating or preventing acne including applying to the skin a therapeutically or prophylactically effective amount of an anti-acne composition according to any one of claims 37 to 45.

47. A method for treating or preventing acne including applying to the skin a therapeutically or prophylactically effective amount of an anti-acne composition including (i) a polymer of 2-propenal, and (ii) a C₃-io alkanediol.

48. A method according to claim 47, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9- nonanediol, 1 ,2-decanediol, 1 ,10-decanediol and neopentyl glycol.

49. A method according to claim 47 or claim 48, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

50. A method according to any one of claims 47 to claim 49, wherein the polymer of 2- propenal is poly(2-propenal, 2-propenoic acid).

51 . Use of (i) a polymer of 2-propenal and (ii) a C₃-ioalkanediol in the manufacture of a medicament for treating or preventing acne.

52. Use according to claim 51 , wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9- nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol.

53. Use according to claim 51 or claim 52, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.

54. Use according to any one of claims 51 to 53, wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

55. An anti-dermatitis composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

56. An anti-dermatitis composition according to claim 55, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5- hexanediol, 1 ,6-hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8- octanediol, 1 ,9-nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, neopentyl glycol.

57. An anti-dermatitis composition according to claim 55 or claim 56, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2- hexanediol and 1 ,2-octanediol.

58. An anti-dermatitis composition according to any one of claims 55 to 57, wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

59. An anti-dermatitis composition according to any one of claims 55 to 58, wherein the composition includes from 0.01 to 10 wt%, preferably from 0.05 to 5 wt%, of the polymer of 2-propenal based on the total weight of the composition.

60. An anti-dermatitis composition according to any one of claims 55 to 59, wherein the composition includes from 0.1 to 99.99 wt%, preferably from 1 to 80 wt%, more preferably 1 to 50 wt% and even more preferably from 1 to 20 wt%, of the C₃--ioalkanediol based on the total weight of the composition.

61 . An anti-dermatitis composition according to any one of claims 55 to 60, further including a C₂--ioalkanol, preferably selected from the group consisting of ethanol and isopropanol.

62. An anti-dermatitis composition according to claim 61 , wherein the ratio of the C₃. -_loalkanediol to the C₂--ioalkanol is between 1 :10 and 10:1 .

63. An anti-dermatitis composition according to any one of claims 55 to 62, further including one or more of a dermatologically acceptable carrier, a stabilizing agent, a thickening agent, a preservative, a skin or hair cleansing agent, a skin softening agent, a fragrance, a dye or a pigment.

64. A method for treating or preventing dermatitis including applying to the skin a therapeutically or prophylactically effective amount of an anti-dermatitis composition according to any one of claims 55 to 63.

65. A method for treating or preventing dermatitis including applying to the skin a therapeutically or prophylactically effective amount of an anti-dermatitis composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.

66. A method according to claim 65, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9- nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, neopentyl glycol.

67. A method according to claim 65 or claim 66, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.

68. A method according to claim 62 or claim 63, wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).

69. Use of (i) a polymer of 2-propenal and (ii) a C₃-ioalkanediol in the manufacture of a medicament for treating or preventing dermatitis.

70. Use according to claim 69, wherein the C3-10 alkanediol includes at least one compound selected from the group consisting of 1 ,2-propanediol, 1 ,3-propanediol, 1 ,2- butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 2,3-butanediol, 1 ,2-pentanediol, 1 ,4- pentanediol, 1 ,5-pentanediol, 2,4-pentanediol, 1 ,2-hexanediol, 1 ,5-hexanediol, 1 ,6- hexanediol, 2,5-hexanediol, 1 ,7-heptanediol, 1 ,2-octanediol, 1 ,8-octanediol, 1 ,9- nonanediol, 1 ,2-decanediol, 1 ,10-decanediol, and neopentyl glycol.

71 . Use according to claim 69 or claim 70, wherein the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.

72. Use according to any one of claims 69 to 71 , wherein the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).