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WO2011047420A1 - Compositions cosmétiques - Google Patents

Compositions cosmétiques Download PDF

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Publication number
WO2011047420A1
WO2011047420A1 PCT/AU2010/001386 AU2010001386W WO2011047420A1 WO 2011047420 A1 WO2011047420 A1 WO 2011047420A1 AU 2010001386 W AU2010001386 W AU 2010001386W WO 2011047420 A1 WO2011047420 A1 WO 2011047420A1
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WO
WIPO (PCT)
Prior art keywords
hexanediol
butanediol
pentanediol
propenal
octanediol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/AU2010/001386
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English (en)
Inventor
Robert William Dunlop
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chemeq Ltd
Original Assignee
Chemeq Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from AU2010100972A external-priority patent/AU2010100972A4/en
Application filed by Chemeq Ltd filed Critical Chemeq Ltd
Publication of WO2011047420A1 publication Critical patent/WO2011047420A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/765—Polymers containing oxygen
    • A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • 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.
  • 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).
  • traumatic lesions such as ulcer
  • 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.
  • MIC minimum inhibitory concentration
  • 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.
  • the present invention relates to a topical antimicrobial composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.
  • 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-octanedi
  • the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the C-3- ⁇ alkanediol includes at least one 1 ,2-C3-ioalkanediol.
  • 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.
  • 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.
  • 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.
  • 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.
  • the polymer of 2-propenal topical antimicrobial typically comprises polymer repeating unit comprising at least one unit type selected from
  • R is H or Ci -4 alkyl, and the hydrated, hemiacetal and acetal forms of the repeating unit.
  • R is hydrogen
  • 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.
  • the polymer of 2-propenal is poly(2- propenal, 2-propenoic acid).
  • 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.
  • 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- i 0 alkanediol. In some specific embodiments the compositions include from 1 to 20 wt% of the C3-ioalkanediol.
  • Topical antimicrobial compositions of the invention may further include a C2- i 0 alkanol.
  • the C 2- ioalkanol is selected from the group consisting of ethanol and isopropanol.
  • the ratio of the C3- ioalkanediol to the is between 1 :10 and 10:1 .
  • 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.
  • 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.
  • 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- ⁇ alkanediol.
  • a topical microbial composition including (i) a polymer of 2-propenal, and (ii) a C-3- ⁇ alkanediol.
  • 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,
  • the C-3- ⁇ alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • 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.
  • the 1 ,2-C 3- i 0 alkanediol is selected from the group consisting of 1 ,2- propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).
  • 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.
  • the C-3- ⁇ 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
  • the C 3- i 0 alkanediol is selected from the group consisting of 1 ,2- propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the polymer of 2-propenal used in the manufacture of the medicament is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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.
  • the present invention also relates to an anti-dandruff composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.
  • the C-3- ⁇ 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,
  • the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the C-3-10 alkanediol includes at least one 1 ,2-C 3- i 0 alkanediol.
  • 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.
  • the C-3- ⁇ alkanediol is a 1 ,2-C3- i 0 alkanediol selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2- hexanediol and 1 ,2-octanediol.
  • the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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- i 0 alkanediol. In some specific embodiments the compositions include from 1 to 20 wt% of the C 3- ioalkanediol.
  • Anti-dandruff compositions of the invention may further include a
  • the C 2 -ioalkanol is selected from the group consisting of ethanol and isopropanol.
  • the ratio of the C3-ioalkanediol to the C2-ioalkanol is between 1 :10 and 10:1 .
  • 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.
  • a dermatologically acceptable carrier e.g., a dermatologically acceptable carrier
  • a stabilizing agent e.g., a stabilizing agent
  • a thickening agent e.g., a preservative, a skin or hair cleansing agent, a skin softening agent, fragrance, a dye or a pigment.
  • 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.
  • 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,
  • the C 3- i 0 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • 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,
  • the 1 ,2-C 3- i 0 alkanediol may be selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).
  • 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.
  • the C 3- i 0 alkanediol used in the manufacture of the medicament includes at least one compound selected from the group consisting of 1 ,2-propanediol,
  • the C 3- i 0 alkanediol is selected from the group consisting of 1,2- propanediol, 1,3-butanediol, 1,2-hexanediol and 1,2-octanediol.
  • the polymer of 2-propenal used in the manufacture of the medicament for treating or preventing dandruff is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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.
  • the C-3- ⁇ 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-oc
  • 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.
  • the C-3-10 alkanediol includes at least one 1,2-C 3- i 0 alkanediol.
  • 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.
  • 1,2-C3-ioalkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2- octanediol.
  • the polymer is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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- i 0 alkanediol.
  • Anti-acne compositions of the invention may further include a C2-ioalkanol.
  • the C2-ioalkanol is selected from the group consisting of ethanol and isopropanol.
  • the ratio of the C3-ioalkanediol to the C 2- ioalkanol is between 1 :10 and 10:1 .
  • 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.
  • 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.
  • 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.
  • 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-octanedii
  • the C3-10 alkanediol is selected from the group consisting of 1 ,2- propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • 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.
  • the 1 ,2-C 3- i 0 alkanediol may be selected from the group consisting of 1 ,2- propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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-hexane
  • the C-3- ⁇ alkanediol is selected from the group consisting of 1 ,2- propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the polymer of 2-propenal used in the manufacture of the medicament for treating acne is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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.
  • the present invention also relates to an anti-dermatitis composition including (i) a polymer of 2-propenal, and (ii) a C3-10 alkanediol.
  • the C-3- ⁇ 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
  • the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the C-3- ⁇ alkanediol is a 1 ,2-C3-ioalkanediol.
  • the 1 ,2-C3- i 0 alkanediol 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.
  • 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.
  • the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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- i 0 alkanediol.
  • Anti-dermatitis compositions of the invention may further include a
  • the C2-ioalkanol is selected from the group consisting of ethanol and isopropanol.
  • the ratio of the C3-ioalkanediol to the C 2- ioalkanol is between 1 :10 and 10:1 .
  • 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.
  • 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.
  • 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.
  • the C-3- ⁇ 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- octane
  • the C-3- ⁇ alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • 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- i 0 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,2-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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-he
  • the C3-10 alkanediol is selected from the group consisting of 1 ,2-propanediol, 1 ,3-butanediol, 1 ,2-hexanediol and 1 ,2-octanediol.
  • the polymer used in the manufacture of a medicament for treating dermatitis is 2-propenal is poly(2-propenal, 2-propenoic acid).
  • 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.
  • 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.
  • 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.
  • compositions of the invention contain a polymer of 2-propenal.
  • Polymers of 2- propenal may have the repeating unit:
  • R is H
  • 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:
  • the molecular weight of the polymer is generally at least 1000 such as in the range of from 1000 to 10,000.
  • 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.
  • the polymer is formed by the anionic polymerization of 2-propenal.
  • the copolymer suitable for use with the invention may be prepared by reacting a suitable precursor polymer.
  • 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).
  • the polymer of 2-propenal is poly(2-propenal, 2-propenoic acid) formed by the oxidation of poly(2-propenal) to introduce carboxyl groups.
  • the poly(2-propenal, 2- propenoic acid) includes from 0.1 to 5 moles of carboxyl groups per kilogram of polymer.
  • 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- ⁇ alkanediol.
  • the C3-10 alkanediol may be substituted or unsubstituted.
  • 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 ,
  • 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.
  • 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.
  • the C-3- ⁇ 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.
  • 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.
  • 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.
  • 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 constituent
  • 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.
  • mixtures of the abovementioned solvents are used.
  • water can be a further constituent.
  • 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
  • imidazoles e.g. urocanic acid
  • peptides such as D,L- carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. a-carotene, ⁇ -carotene, lycopene) and their derivatives
  • lipoic acid and its derivatives e.g. dihydrolipoic acid
  • aurothioglucose propylthiouracil and other thiols
  • thioredoxin glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -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 e.g. a-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), a- hydroxy acids (e.g.
  • citric acid 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. ⁇ -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
  • 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.
  • 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.
  • 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.
  • these polymers are ethers of Cio-C 30 straight or branched chain alcohols with hydroxyalkylcelluloses.
  • 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.
  • 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.
  • acacia agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrage
  • compositions according to the invention may further include preservatives. Suitable preservatives include, but are not limited to, Ci-C 4 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.
  • 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
  • any counter cation can be used in the anionic surfactant.
  • the counter cation is selected from the group consisting of sodium, potassium, and counter cations derived from diethanolamine, or triethanolamine.
  • the counter cation is sodium or potassium.
  • 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.
  • composition 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.
  • 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.
  • alcohol ethoxylates such as fatty alcohol ethoxylates and/or propoxylates
  • alkyl phenolethoxylates alkyl phenolethoxylates
  • glycol ester surfactants PEG(20) sorbitan monooleate
  • polyethylene glycol cocoate propylene oxide/ethylene oxide block polymers
  • alkanolamines and mixtures thereof.
  • 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.
  • 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.
  • alkyl betaines oleyl
  • 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.
  • 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.
  • 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.
  • top note i.e. fragrances having a high vapor pressure
  • middle note i.e. fragrance having a medium vapor pressure
  • base note i.e. fragrances having a low vapor pressure
  • 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.
  • 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.
  • 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 die
  • fragrances examples 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.
  • 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%.
  • dyes suitable for use with the compositions of the invention will be dermatologically acceptable dyes.
  • fat-soluble dyes include Soudan red, D & C Red 17, D & C Green 6, ⁇ -carotene, soybean oil, Soudan brown, D & C Yellow 1 1 , D & C Violet 2, D & C Orange 5, and quinoline yellow.
  • water-soluble dyes include beet juice and methylene blue.
  • 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.
  • 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.
  • compositions of the invention may be formulated as any type of formulation appropriate for application to the skin or hair.
  • 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.
  • 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.
  • 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.
  • the methods of the invention will be applied in association with other treatments or methods.
  • 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.
  • the methods of the invention might involve the application of compositions of the invention as a conditioner in association with an appropriate shampoo.
  • 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.
  • 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).
  • 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.
  • 0.2M aqueous sodium hydroxide (21 .4 mL) was added to bring the pH to 10.5 - 1 1 .0.
  • 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.
  • 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.
  • Poly(2-propenal, 2-propenoic acid) produced by either oxidation method have identical physicochemical and antimicrobial properties.
  • 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
  • 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
  • fragrance dye, 1 .0 1 .0 1 .0 1.0 thickeners
  • 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
  • Example 32 Shampoo Formulations: Poly(2-propenal, 2-propenoic acid) and 1 ,2- decanediol
  • 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)
  • 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.
  • a control placebo was prepared by combining the following components in the amounts by weight specified.
  • 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.
  • PPPA poly(2-propenal, 2-propenoic acid)
  • 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.
  • 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.
  • 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 .
  • 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.
  • 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:
  • 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.
  • test panelists 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.
  • 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 49 Oil in Water SPF 15 Formulations Benzethoniumchloride 0.5
  • Macadamia Ternifolia 1 0.75 1.3 1 .3

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Abstract

La présente invention concerne une composition antimicrobienne topique comprenant (i) un polymère de 2-propénal, et (ii) un alcanediol en C3-10.
PCT/AU2010/001386 2009-10-19 2010-10-19 Compositions cosmétiques Ceased WO2011047420A1 (fr)

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Cited By (14)

* Cited by examiner, † Cited by third party
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JP2013095754A (ja) * 2011-11-04 2013-05-20 Symrise Ag 相乗的に作用する、３成分抗菌性混合物
WO2014009157A1 (fr) 2012-07-13 2014-01-16 L'air Liquide,Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Mélange d'alcools naturels ou identiques à des alcools naturels à efficacité améliorée
WO2014047428A1 (fr) * 2012-09-21 2014-03-27 Segetis, Inc. Compositions de nettoyage, de tensioactif et de soins personnels
US20140135349A1 (en) * 2012-11-11 2014-05-15 Symrise Ag Aqueous Compositions
US9023774B2 (en) 2009-06-22 2015-05-05 Segetis, Inc. Ketal compounds and uses thereof
EP2878292A3 (fr) * 2013-11-21 2015-08-12 Henkel AG & Co. KGaA Utilisation de compositions cosmétiques pour l'inactivation et/ou l'élimination d'acariens de la peau
US9156809B2 (en) 2012-11-29 2015-10-13 Segetis, Inc. Carboxy ester ketals, methods of manufacture, and uses thereof
US9206275B2 (en) 2008-09-25 2015-12-08 Segetis, Inc. Ketal ester derivatives
JP2019510731A (ja) * 2016-02-19 2019-04-18 レッセ ファーマシューティカルズ リミテッドＲｅｃｃｅ Ｌｉｍｉｔｅｄ 抗ウイルス薬およびウイルス感染症の治療方法
EP3501488A1 (fr) * 2017-12-21 2019-06-26 Momentive Performance Materials GmbH Compositions aqueuses de polymère de silicone
WO2020015827A1 (fr) * 2018-07-18 2020-01-23 Symrise Ag Composition détergente
WO2020094244A1 (fr) * 2018-11-08 2020-05-14 Symrise Ag Composition antimicrobienne à base de tensioactif
US20200405659A1 (en) * 2018-02-27 2020-12-31 Gs Caltex Corporation Composition containing 2,3-butanediol as active ingredient
WO2023049981A1 (fr) 2021-10-01 2023-04-06 Chemyunion Ltda. Composition anti-sébogène, formulation et utilisation de cette composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002026211A1 (fr) * 2000-09-27 2002-04-04 Chemeq Ltd Emulsion antimicrobienne polymere topique

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002026211A1 (fr) * 2000-09-27 2002-04-04 Chemeq Ltd Emulsion antimicrobienne polymere topique

Cited By (25)

* Cited by examiner, † Cited by third party
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US9206275B2 (en) 2008-09-25 2015-12-08 Segetis, Inc. Ketal ester derivatives
US9023774B2 (en) 2009-06-22 2015-05-05 Segetis, Inc. Ketal compounds and uses thereof
JP2013095754A (ja) * 2011-11-04 2013-05-20 Symrise Ag 相乗的に作用する、３成分抗菌性混合物
WO2014009157A1 (fr) 2012-07-13 2014-01-16 L'air Liquide,Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Mélange d'alcools naturels ou identiques à des alcools naturels à efficacité améliorée
US9883671B2 (en) 2012-07-13 2018-02-06 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Mixture of natural or nature-identical alcohols with improved effectiveness
WO2014047428A1 (fr) * 2012-09-21 2014-03-27 Segetis, Inc. Compositions de nettoyage, de tensioactif et de soins personnels
US9458414B2 (en) 2012-09-21 2016-10-04 Gfbiochemicals Limited Cleaning, surfactant, and personal care compositions
US20140135349A1 (en) * 2012-11-11 2014-05-15 Symrise Ag Aqueous Compositions
US9468644B2 (en) * 2012-11-11 2016-10-18 Symrise Ag Aqueous compositions
US9156809B2 (en) 2012-11-29 2015-10-13 Segetis, Inc. Carboxy ester ketals, methods of manufacture, and uses thereof
EP2878292A3 (fr) * 2013-11-21 2015-08-12 Henkel AG & Co. KGaA Utilisation de compositions cosmétiques pour l'inactivation et/ou l'élimination d'acariens de la peau
JP2019510731A (ja) * 2016-02-19 2019-04-18 レッセ ファーマシューティカルズ リミテッドＲｅｃｃｅ Ｌｉｍｉｔｅｄ 抗ウイルス薬およびウイルス感染症の治療方法
EP3501488A1 (fr) * 2017-12-21 2019-06-26 Momentive Performance Materials GmbH Compositions aqueuses de polymère de silicone
US10947383B2 (en) 2017-12-21 2021-03-16 Momentive Performance Materials Gmbh Aqueous silicone polymer compositions
US20200405659A1 (en) * 2018-02-27 2020-12-31 Gs Caltex Corporation Composition containing 2,3-butanediol as active ingredient
JP2021514986A (ja) * 2018-02-27 2021-06-17 ジーエス カルテックス コーポレーションＧｓ Ｃａｌｔｅｘ Ｃｏｒｐｏｒａｔｉｏｎ ２、３−ブタンジオールを有効成分として含む組成物
WO2020015827A1 (fr) * 2018-07-18 2020-01-23 Symrise Ag Composition détergente
CN112534031A (zh) * 2018-07-18 2021-03-19 德国德之馨香精香料公司 洗涤剂组合物
KR20210032993A (ko) * 2018-07-18 2021-03-25 시므라이즈 아게 세제 조성물
JP2021531383A (ja) * 2018-07-18 2021-11-18 シムライズ アーゲー 洗剤組成物
JP7304933B2 (ja) 2018-07-18 2023-07-07 シムライズ アーゲー 洗剤組成物
KR102657240B1 (ko) * 2018-07-18 2024-04-12 시므라이즈 아게 세제 조성물
US12264299B2 (en) 2018-07-18 2025-04-01 Symrise Ag Detergent composition
WO2020094244A1 (fr) * 2018-11-08 2020-05-14 Symrise Ag Composition antimicrobienne à base de tensioactif
WO2023049981A1 (fr) 2021-10-01 2023-04-06 Chemyunion Ltda. Composition anti-sébogène, formulation et utilisation de cette composition

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