WO2004006883A1 - Compositions cosmetiques de soins de beaute contenant des carboxyalkylates d'alcools ramifies et/ou des alkoxylates associes - Google Patents

Compositions cosmetiques de soins de beaute contenant des carboxyalkylates d'alcools ramifies et/ou des alkoxylates associes Download PDF

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Publication number
WO2004006883A1
WO2004006883A1 PCT/EP2003/007649 EP0307649W WO2004006883A1 WO 2004006883 A1 WO2004006883 A1 WO 2004006883A1 EP 0307649 W EP0307649 W EP 0307649W WO 2004006883 A1 WO2004006883 A1 WO 2004006883A1
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Prior art keywords
skin
aluminum
integer
compound
cation
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PCT/EP2003/007649
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English (en)
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WO2004006883A8 (fr
Inventor
Bijan Harichian
Carol Annette Bosko
John Steven Bajor
Laurence Khiyen Boen
Surajit Mukherjee
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Unilever Plc
Unilever Nv
Hindustan Lever Limited
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Priority claimed from US10/196,881 external-priority patent/US20040013630A1/en
Priority claimed from US10/196,770 external-priority patent/US6916851B2/en
Application filed by Unilever Plc, Unilever Nv, Hindustan Lever Limited filed Critical Unilever Plc
Priority to JP2005505071A priority Critical patent/JP2005539093A/ja
Priority to MXPA05000679A priority patent/MXPA05000679A/es
Priority to CN038170345A priority patent/CN1668274B/zh
Priority to AU2003254356A priority patent/AU2003254356B2/en
Publication of WO2004006883A1 publication Critical patent/WO2004006883A1/fr
Publication of WO2004006883A8 publication Critical patent/WO2004006883A8/fr

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Classifications

    • 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
    • A61Q19/08—Anti-ageing preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides 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
    • A61K8/18—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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61Q19/008—Preparations for oily skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms

Definitions

  • Cosmetic methods and compositions for conditioning human skin by topical application to the skin of cosmetic compositions which contain carboxyalkylates of branched alcohols, and/or alkoxylates thereof alone or in combination with astringent salts.
  • Sebum is skin oil which is produced by sebocytes (cells of the sebaceous glands in the skin) and is then secreted to the skin surface.
  • a frequent and undesirable skin condition is "oily skin,” the condition which results from the excessive amount of sebum on the skin. Oily skin is associated with a shiny, undesirable appearance and a disagreeable tactile sensation. This condition affects various age groups. Therefore, cosmetic products which provide both sebum control and anti -aging benefits are highly desirable.
  • branched alcohols as compounds which provide skin benefits such as sebum suppression.
  • Burger et al . U.S. Patent No. 5,756,109 relates to the use of a noncyclic polyunsaturated diterpene alcohol, geranyl geraniol, in combination with a retinol as a skin conditioning composition.
  • This patent discloses sebum suppression as one advantage of the branched alcohol in combination withretinol.
  • Hata et al . U.S. Patent No. 5,344,850 discloses topical compositions containing a .8 saturated or unsaturated alcohol with four methyl branches for treating or preventing acne.
  • WO 9918928 assigned to The Proctor & Gamble Company, discloses personal cleansing compositions comprising branched surfactant systems having a hydrophobic group and a hydrophilic group.
  • the hydrophobic group comprises mid-chain branched and linear surfactant compounds.
  • the hydrophilic group is selected from the group consisting of sulfate and/or ethoxylates thereof.
  • Cripe et al . , US Patent 6,020,303 discloses detergent surfactant compositions derived from mid-chain branched primary alkyl hydrophobic groups and hydrophilic groups, specifically, alkyl sulfates for application in laundry and cleaning compositions.
  • Birtwistle et al . , US Patent No. 5,093,112 discloses topical cleansing (detergent) compositions containing an alcohol and an alkyl or alkenyl phosphate salt.
  • compositions or methods for skin conditioning which further improve the effects and perceived effects of branched alcohols and carboxyalkylates of branched alcohols.
  • compositions containing antiperspirants to improve the staying power of the colour are disclosed in L'Oreal's Bazin et al., U.S. Patent No. 6,251,412.
  • Use of antiperspirant active ingredients for the manufacture of preparations for removal of sebum from the skin, in particular for the removal and clearing of comedones, for avoiding comedone formation, for the prophylaxis and treatment of mild forms of acne, and for the prophylaxis and control of seborrhea is disclosed in Herpens et al . , U.S. Published Patent Application 2002/0119109.
  • a combination of astringent salts and carboxyalkylates of branched alcohols has not been previously used for improving skin feel through a combined synergistic effect of sebum suppression and sweat suppression. Therefore, a need remains for novel cosmetic compositions that retain or enhance the beneficial effects of carboxyalkylates of branched alcohols in relation to sebum suppression and skin conditioning, while providing improved perception of reduced shine or oily/greasy skin.
  • R is a branched alkyl or alkenyl chain having at least 7 carbon atoms, and at least two branches; 0 is an oxygen atom; and
  • M is (-(CH 2 ) p O) n - (CH 2 ) m C0 2 X where n is 0 or an integer between 1 and 7, m is an integer between 2 and 4, p is an integer between 2 and 4; and X is hydrogen, a methyl group, an ethyl group, or a cation.
  • the cation is preferably selected from the group consisting of sodium, lithium, potassium, calcium, copper, magnesium, manganese, strontium, sulfur, zinc, and amines.
  • X is hydrogen or a cation.
  • an inventive process involves reacting a branched alcohol with acrylonitrile, followed by reacting the alkyl ether nitrile with aqueous solution of acid, such as hydrochloric acid or sulfuric acid, to form carboxyethyl iso- alcohol .
  • the carboxyethyl iso-alcohol may further be reacted with an alcohol or base to form compound of formula A
  • the present invention provides a process of synthesising a compound of the formula A comprising:
  • the inventive composition includes an astringent salt.
  • the skin care cosmetic compositions include an astringent salt selected from the group consisting ofaluminum chloride, aluminum chlorohydrate, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohydrex PEG, aluminum sesquichlorohydrex PG, aluminum sulfate, aluminum zirconium octachlorohydrate, aluminum zirconium octachlorohydrex GLY, aluminum zirconium pentachlorohydrate, aluminum zirconium pentachlorohydrex GLY, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate GLY, and aluminum zirconium trichlorohydrate GLY, and mixtures thereof .
  • an astringent salt selected from the group consisting ofalumin
  • the present invention further includes a skin care cosmetic composition comprising compound A in a cosmetically acceptable vehicle.
  • the cosmetic composition may further include retinoids .
  • the present invention also includes a cosmetic method of controlling or preventing an oily skin condition and/or perception thereof and preventing or controlling sebum secretion from sebocytes, especially in the facial area, by applying to the skin the inventive compositions.
  • the invention also includes a cosmetic method of reducing, preventing or controlling sebum secretion fromsebocytes by applying the in inventive composition.
  • the inventive methods are also useful for reducing or preventing secretion from the apocrine glands.
  • the invention also includes a cosmetic method of stimulating collagen synthesis by fibroblasts in the skin, by applying to the skin the inventive composition.
  • inventive methods and compositions provide control of sebum secretion from sebocytes, improved oil control, improved skin feel, they prevent shine and stickiness. They also provide anti-microbial activity against bacteria associated with acne, as well as providing anti-aging benefits which result in reduced appearance of wrinkles and aged skin, improved skin colour, treatment of photoaged skin, improvement in skin's radiance and clarity and finish, and an overall healthy and youthful appearance of the skin.
  • the term “comprising” means including, made up of, composed of, consisting and/or consisting essentially of.
  • skin as used herein includes the skin on the face, neck, chest, back, arms, hands, legs and scalp.
  • suppression as used herein in relation to sebum and/or sweat means the complete prevention, control of secretion, or a degree of reduction of the formation of sebum and/or sweat, respectively.
  • inventive methods and compositions include a carboxyalkylate of a branched alcohol, and/or alkoxylates thereof (hereinafter “compound A”) , and are of the general formula A:
  • R is a branched alkyl or alkenyl chain having at least 7 carbon atoms, generally from 9 to 15 atoms, and at least two branches ;
  • O is an oxygen atom;
  • M is (- (CH 2 ) p O) n - (CH ) m C0 2 X, where n is 0 or an integer between
  • m is an integer between 2 and 4
  • p is an integer between 2 and 4
  • X is hydrogen, a methyl group, an ethyl group, or a cation.
  • the cation may be selected from the group consisting of sodium, lithium, potassium, calcium, magnesium, manganese, sulfur, and amines including quartenary alkyl amines and polyhydroxy amines, but is not limited thereto.
  • X is a hydrogen or a cation and M is: -CH 2 CH 2 C0 2 X (n is 0, m is 2)
  • X is a hydrogen or a cation and M is: -CH 2 CH 2 C0 2 X (n is 0, m is 2) or
  • the branched alkyl chain of the present invention is preferably derived from a branched alcohol having 7 to 15 carbon atoms, more preferably at least 9 carbon atoms and at least two branches, as noted above.
  • the preferred alcohols from which the inventive compositions are derived contain a total of at least 10 carbon atoms in order to obtain maximum efficacy, with 13 carbon atoms most preferred.
  • the preferred alcohols from which the inventive compositions are derived contain from 2 to 5 branches, more preferably 3 to 4 branches, in order to maximize efficacy at minimum cost.
  • the branches may be methyl branches, ethyl branches, or propyl branches.
  • the branches are methyl branches or ethyl branches, most preferably methyl branches, due to reduced odour and enhanced efficacy.
  • the alcohol may be a mixture of various chain length alcohols. Such mixtures are suitable in deriving the inventive compositions, as long as the predominant alcohol (at least about 70%) in the mix contains a total of at least 7, preferably at least 9, optimally 13, carbon atoms and at least two branches .
  • Examples of preferred compounds of formula A are carboxyethylates of branched alcohols and/or ethoxylates thereof.
  • the most preferred compounds of formula A are carboxyethyl tridecylisoalcohols (TDCE) and salts thereof.
  • Carboxyethylates of branched alcohols may be synthesized by the following process. (branched alcohol ) (acrylonitrile)
  • carboxyethylation of the branched alcohol involves the addition of a carboxy-ethyl group to the branched alcohol.
  • Compound of formula A is derived from branched alcohols which are commercially available, e.g. from Exxon or Henkel .
  • Step 1 etherification, involves first directly adding an acrylonitrile (available, for example, from Aldrich Chemicals) to the branched alcohol to form an alkyl or alkenyl ether nitrile, also referred to as alkyl or alkenyl oxypropionitrile.
  • the acrylonitrile may be used in a 1:1 molar ratio to the branched alcohol, or in excess in order to drive the reaction forward and enhance yield.
  • the molar ratio of branched alcohol to acrylonitrile is 1:1.5.
  • Step 2 the alkyl or alkenyl ether nitrile is reacted with an aqueous solution of an acid, such as hydrochloric acid or sulfuric acid, at room/ambient temperature, over potassium hydroxide or sodium hydroxide catalyst, to yield carboxyethyl isoalcohol.
  • the carboxyethyl isoalcohol may be further reacted with an alcohol or base, such as MeOH or NaOH, to form an R-O-M structure (A) as discussed above, such as wherein X is a methyl group or the cation sodium.
  • the salt forms of compound A are preferred because they are water soluble for penetration through the skin.
  • sodium salt is used because of commercial availability.
  • Tridecylcarboxyethylate is the most preferred carboxyalkylate of branched alcohol compound, due to water solubility and oil solubility properties which translate into effective skin activity and further to cost effectiveness due to the ability to use a smaller amount of active to gain a given degree of benefit. Additionally, TDCE has more acceptable odour and colour characteristics than other similar molecules, particularly TDCM (tridecylcarboxymethylate) .
  • Compound A of the present invention retains or enhances the beneficial sebum suppression qualities of branched alcohols and methoxylates thereof, while eliminating the unpleasant odour and colour.
  • compound A is an anionic surfactant, thus providing a negative charge that aids in binding the surfactant onto the skin's surface.
  • the water soluble characteristic effectuates delivery into the skin.
  • the carboxyl group in compound A is a better metal chelator and milder to the skin due to its relatively low acidity (pKa of approximately 3) .
  • the carboxyl group has a lower molecular weight than a sulfate group, thus lower amounts of the carboxyl group will yield more beneficial results than the sulfate group.
  • Compounds of formula A are employed in the inventive methods and compositions in amounts of about 0.001% to about 50%, preferably about 0.1% to about 20%, most preferably about 0.1% to about 10%.
  • Compositions employing compounds of formula A may optionally, but preferably, include astringent salts.
  • astringent salts include astringent salts.
  • the perception of oily/greasy skin, especially facial skin can be indirectly controlled by reducing the amount of facial sweating and controlling sebum, i.e. through suppression of sweat and sebum secretion.
  • the astringent salts may be inorganic or organic salts of aluminum, zirconium, zinc and mixtures thereof.
  • the astringent salts are employed herein in particulate form, i.e., hydrophilic porous particles, of less than about 100 microns in size, preferably about 3 microns to about 10 microns in size.
  • Salts useful as astringents or as components of astringent aluminum complexes include aluminum hydroxide, aluminum halides, aluminum hydroxyhalides, zirconyl oxyhalides, zirconyl hydroxyhalides and mixtures of these salt materials.
  • Aluminum salts of this type include aluminum chloride and the aluminum hydroxyhalides having the general formula
  • aluminum chlorohydrate having the formula [Al 2 (OH) 5 CI] --
  • XH 2 0 is preferred, due to its ready commercial availability and relatively low cost.
  • Spherical ZAG with particle size 1 to 100 microns, is especially preferred.
  • astringent salts which may be useful for the present invention and which have approved listings under the United States Food & Drug Administration, Federal Register. They include aluminum chloride, aluminum chlorohydrate, aluminum chlorohydrex, aluminum chlorohydrex PEG, aluminum chlorohydrex PG, aluminum dichlorohydrate, aluminum dichlorohydrex PEG, aluminum dichlorohydrex PG, aluminum sesquichlorohydrate, aluminum sesquichlorohydrex PEG, aluminum sesquichlorohydrex PG, aluminum sulfate, aluminum zirconium octachlorohydrate, aluminum zirconium octachlorohydrex GLY (abbreviation for glycine) , aluminum zirconium pentachlorohydrate, aluminum zirconium pentachlorohydrex GLY, aluminum zirconium tetrachlorohydrate, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate GLY, and aluminum zirconium
  • potassium aluminium sulphate also known as alum
  • the antiperspirant is an aluminium salt and, more preferably, it is chosen from potassium aluminium sulphate and aluminium chlorohydrate.
  • Amounts of the active astringent salt may range from about 0.000001% to about 20%, preferably from about 0.10% to about 18%, more preferably about 1% to about 15%, andoptimally about 2% to about 3% by weight of the composition.
  • Aluminum chlorohydrate referred to herein in shortened form as ACH, is the most preferred astringent salt for the purposes of the present invention, due to its wide commercial availability and relatively low cost.
  • the inventive compositions may also include a retinoid.
  • Retinoids increase collagen synthesis by dermal fibroblasts. This results in protection from sun damage and smoothening of wrinkled skin. Addition of retinoids to compound A provided improved inhibition of lipogenesis; as well as increased collagen synthesis in comparison to compound A alone.
  • retinoids as used herein includes retinoic acid, retinol, retinal, and retinyl esters. Included in the term “retinoic acid” are 13-cis retinoic acid and all-trans retinoic acid.
  • retinol as used herein includes the following isomers of retinol: all-trans-retinol , 13-cis-retinol, 11- cis-retinol, 9-cis-retinol and 3 ,4-didehydro-retinol .
  • Preferred isomers are all-trans-retinol, 13-cis-retinol, 3,4- didehydro-retinol, and 9-cis-retinol. Most preferred is all- trans-retinol, due to its wide commercial availability.
  • Retinyl ester is an ester of retinol.
  • the term "retinol 1 has been defined above.
  • Retinyl esters suitable for use in the present invention are .-C 30 esters of retinol, preferably Q- C o esters, and most preferably Q>, C 3 , and Cig esters because they are more commonly available.
  • Suitable retinyl esters include but are not limited to: retinyl palmitate, retinyl formate, retinyl acetate, retinyl propionate, retinyl butyrate, retinyl valerate, retinyl isovalerate, retinyl hexanoate, retinyl heptanoate, retinyl octanoate, retinyl nonanoate, retinyl decanoate, retinyl undecanoate, retinyl laurate, retinyl tridecanoate, retinyl myristate, retinyl pentadecanoate, retinyl heptadecanoate, retinyl stearate, retinyl isostearate, retinyl nonadecanoate, retinyl arachidonate, retinyl behenate,
  • the retinoids in the present invention are typically present in an amount of from 0.001% to 10%, preferably from 0.01% to 1%, and most preferably from 0.01% to 0.05% by weight of the composition.
  • compositions according to the invention comprise a cosmetically acceptable vehicle to act as a diluant, dispersant or carrier of compound A, so as to facilitate their distribution when the composition is applied to the skin.
  • the vehicle may be aqueous, anhydrous or an emulsion.
  • the compositions are aqueous or an emulsion, especially water-in-oil or oil-in-water emulsion.
  • Water when present will be in amounts which may range from 5% to 99%, preferably from 40% to 90%, optimally between 60% and 90% by weight .
  • relatively volatile solvents may also serve as carriers within compositions of the present invention.
  • monohydric . -C 3 alkanols include ethyl alcohol, methyl alcohol and isopropyl alcohol.
  • the amount of monohydric alkanol may range from 1% to 70%, preferably from 10% to 50%, optimally between 15% and 40% by weight.
  • Emollient materials may also serve as cosmetically acceptable carriers. These may be in the form of silicone oils and synthetic esters. Amounts of the emollients may range anywhere from 0.1% to 50%, preferably between 1% and 20% by weight .
  • Silicone oils may be divided into the volatile and nonvolatile variety.
  • volatile refers to those materials which have a measurable vapor pressure at ambient temperature.
  • Volatile silicone oils are preferably chosen from cyclic or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms. Linear volatile silicone materials generally have viscosities less than about 5 centistokes at 25°C while cyclic materials typically have viscosities of less than about 10 centistokes.
  • Non-volatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers.
  • the essentially non-volatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from about 5 to about 25 million centistokes at 25°C.
  • the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from about 10 to about 400 centistokes at 25°C.
  • ester emollients are:
  • (l)Alkenyl or alkyl esters of fatty acids having 10 to20 carbon atoms examples thereof include isoarachidyl neopentanoate, isononyl isonanonoate, oleyl myristate, oleyl stearate, and oleyl oleate.
  • Ether-esters such as fatty acid esters of ethoxylated fatty alcohols .
  • Ethylene glycol mono and di- fatty acid esters diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monooleate, polypropylene glycol
  • Wax esters such as beeswax, spermaceti, myristyl myristate, stearyl stearate and arachidyl behenate .
  • Steprols esters of which cholesterol fatty acid esters are examples .
  • Fatty acids having from 10 to 30 carbon atoms may also be included as cosmetically acceptable carriers for compositions of this invention.
  • Illustrative of this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic and erucic acids.
  • Humectants of the polyhydric alcohol type may also be employed as cosmetically acceptable carriers in compositions of this invention.
  • the humectant aids in increasing the effectiveness of the emollient, reduces scaling, stimulates removal of built- up scale and improves skin feel.
  • Typical polyhydric alcohols include glycerol, polyalkylene glycols and more preferably alkylene polyols and their derivatives, including propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol and derivatives thereof, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene glycol, 1,2,6- hexanetriol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof.
  • the humectant is preferably propylene glycol or sodium hyaluronate .
  • the amount of humectant may range anywhere from 0.5% to 30%, preferably between 1% and 15% by weight of the composition.
  • Thickeners may also be utilized as part of the cosmetically acceptable carrier of compositions according to the present invention.
  • Typical thickeners include crosslinked acrylates (e.g. Carbopol 982), hydrophobically-modified acrylates (e.g.
  • Carbopol 1382 cellulosic derivatives and natural gums.
  • useful cellulosic derivatives are sodium carboxymethylcellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, ethyl cellulose and hydroxymethyl cellulose.
  • Natural gums suitable for the present invention include guar, xanthan, sclerotium, carrageenan, pectin and combinations of these gums. Amounts of the thickener may range from 0.0001% to 5%, usually from 0.001% to 1%, optimally from 0.01% to 0.5% by weight.
  • the water, solvents, silicones, esters, fatty acids, humectants and/or thickeners will constitute the cosmetically acceptable carrier in amounts from 1% to 99.9%, preferably from 80% to 99% by weight.
  • An oil or oily material may be present, together with an emulsifier to provide either a water-in-oil emulsion or an oil-in-water emulsion, depending largely on the average hydrophilic-lipophilic balance (HLB) of the emulsifier employed.
  • HLB hydrophilic-lipophilic balance
  • Actives are defined as skin benefit agents other than emollients and other than ingredients that merely improve the physical characteristics of the composition.
  • additional anti-sebum ingredients such as talcs and silicas, as well as alpha-hydroxy acids, beta-hydroxy acids, poly-hydroxy acids, benzoyl peroxide, zinc salts, and sunscreens.
  • Beta-hydroxy acids include salicylic acid, for example.
  • Zinc pyrithione is an example of zinc salts useful in the compositions of the present invention.
  • Sunscreens include those materials commonly employed to block ultraviolet light.
  • Illustrative compounds are the derivatives of PABA, cinnamate and salicylate.
  • avobenzophenone Parsol 1785®
  • octyl methoxycinnamate and 2- hydroxy-4-methoxy benzophenone (also known as oxybenzone) can be used.
  • Octyl methoxycinnamate and 2-hydroxy-4-methoxy benzophenone are commercially available under the trademarks, Parsol MCX and Benzophenone-3 , respectively.
  • the exact amount of sunscreen employed in the compositions can vary depending upon the degree of protection desired from the sun's UV radiation.
  • Suitable preservatives include alkyl esters of phydroxybenzoic acid, hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds.
  • Particularly preferred preservatives of this invention are methyl paraben, propyl paraben, phenoxyethanol and benzyl alcohol. Preservatives will usually be employed in amounts ranging from about 0.1% to 2% by weight of the composition.
  • the compounds and compositions according to the invention are intended primarily as a product for topical application to human skin, especially as an agent for controlling or preventing excessive sebum secretion.
  • Suppression of sebum provides multiple benefits, including: improved skin condition; reduction of an unpleasant appearance and feel of greasy skin; reduction and/or prevention of acne, rosacea, seborrhea, oily scalp, oily/greasy hair, and dandruff.
  • Suppression of sweat provides multiple benefits, including improved skin condition and reduction of an unpleasant appearance and feel of shiny skin. Suppression of both sebum and sweat enhances the multiple benefits of suppression of sebum and suppression of sweat, to the point of improving the perception of oily or greasy or shiny skin.
  • a quantity of the composition for example from 1 to 100 ml, is applied to exposed areas of the skin, from a suitable container or applicator and, if necessary, it is then spread over and/or rubbed into the skin using the hand or fingers or a suitable device.
  • the present invention also includes a cosmetic method of controlling or preventing an oily skin condition, especially in the facial area, by applying to the skin the inventive composition.
  • the present invention includes a cosmetic method of controlling, preventing, or treating oily or greasy hair.
  • the invention also includes a cosmetic method of reducing, preventing or controlling sebum secretion from sebocytes by applying the inventive composition.
  • the invention also includes a cosmetic method of reducing or controlling the perception of oily or greasy skin by applying to the skin the inventive composition.
  • the invention also includes a cosmetic method of stimulating collagen synthesis by fibroblasts in the skin, by applying to the skin the inventive composition.
  • inventive methods and compositions provide control of sebum secretion from sebocytes, improved oil control and improved skin feel, and prevent shine and stickiness, while also providing anti-microbial activity against bacteria associated with acne and, generally, controlling microbial activity of bacteria on the skin surface, as well as providing anti-aging benefits which result in reduced appearance of wrinkles and aged skin, improved skin colour, treatment of photoaged skin, improvement in skin's radiance and clarity and finish, and an overall healthy and youthful appearance of the skin. Additionally, the compositions of the present invention reduce or prevent secretion from the apocrine glands.
  • the cosmetic skin composition of the invention can be in any form, e.g. formulated as a toner, gel, lotion, a fluid cream, or a cream.
  • the composition can be packaged in a suitable container to suit its viscosity and intended use by the consumer.
  • a lotion or fluid cream can be packaged in a bottle or a roll-ball applicator or a propel1ant-driven aerosol device or a container fitted with a pump suitable for finger operation.
  • the composition is a cream, it can simply be stored in a non-deformable bottle or squeeze container, such as a tube or a lidded jar.
  • the invention accordingly also provides a closed container containing a cosmetically acceptable composition as herein defined.
  • composition may also be included in capsules such as those described in U.S. Patent No. 5,063,057, incorporated by reference herein.
  • Exxal ,® 9 About 33% dimethyl heptanol
  • Exxa ,l® 10 Trimethyl heptanols and dimethyl octanols
  • Nonanol About 80% 3, 5, 5-trimethylhexanol d Acropol 35 About 70% C 13 ; about 63% dimethyl branching Exxal 13 and Acropol 35 are preferred alcohols, and Exxa 13 is the more preferred alcohol .
  • This example provided carboxymethylation of an alcohol, which yields carboxymethylates of isoalcohols with a purity of about 50% to about 70%.
  • Potassium tertiary-butoxide (9.42g, 0.084mole) was weighed out into a small round bottom flask under moisture free atmosphere (N 2 dry box) . To this was then added 25ml dry p- dioxane and while stirring, a mixture of Exxal ® 13 alcohol (4.0g, 0.02mole) and chloroacetic acid (1.89g, 0.02mole) in 15ml dry p-dioxane was added. The heterogeneous reaction mixture was then stirred and heated at slight reflux overnight under N 2 . The overnight heating caused a slight colouration to the mixture.
  • This example provided carboxyethylation of a branched alcohol, which yields carboxyethylates of iso-alcohols (iso-tridecyloxy propionic acid) with a purity of about 98% to about 99%.
  • the iso-tridecyloxypropionitrile (2 g) and 8 ml concentrated hydrochloric acid were charged into a small 3-neck round- bottom flask fitted with a mechanical stirrer and condenser and heated at 75-80°C (water bath) for one hour and then at reflux for 3 hours.
  • the aqueous layer was extracted with 20 ml chloroform and dried. Note, hexane extraction may also be used.
  • the chloroform was completely removed (Rotavap) , yielding about 2.0 g clear colourless liquid product. This was analyzed by gas chromatography (GC) and infrared spectroscopy (IR: strong carbonyl band at 1722 cm ) to be the carboxyethyl iso-tridecanol product.
  • GC gas chromatography
  • IR infrared spectroscopy
  • the purity of the carboxyethyl iso-tridecanol product is at least about 98%.
  • Potential by products are: ammonium chloride, dimer of TDCE, ester of TDCE.
  • This example provided comparative data on inhibition of sebocyte lipogenesis by the carboxymethylated and the carboxyethylated products of Examples 1 and 2, respectively.
  • the iso-tridecyl carboxymethylated product and the iso- tridecyl carboxyethylated products (hereinafter "TDCM” and “TDCE”, respectively) and sodium salts thereof were obtained from Examples 1 and 2, respectively.
  • Sebocyte growth medium consisted of Clonetics Keratinocyte Basal Medium (KBM) supplemented with 14 ⁇ g/ml bovine pituitary extract, 0.4 ⁇ g/ml hydrocortisone, 5 ⁇ g/ml insulin, 10 ng/ml epidermal growth factor, 1.2 x 10 "10 M cholera toxin, 100 units/ml penicillin, and 100 ⁇ g/ml streptomycin. All cultures were incubated at 37°C in the presence of 7.5% C0 . Medium was changed three times per week.
  • DMEM Dulbecco's Modified Eagle Medium
  • Fresh DMEM was added to each sample (duplicates, triplicates, or quadruplicates depending on the experiment) with 5 ⁇ L of test agent solubilized in ethanol or sterile, distilled water.
  • Controls consisted of addition of ethanol alone or phenol red. Phenol Red, a known sebum suppressive agent, was employed as a positive control .
  • Each plate was returned to the incubator for 20 hours followed by the addition of 14 C-acetate buffer (5 mM final concentration, 56 mCi/mmol specific activity) .
  • Sebocytes were returned to the incubator for four hours after which each culture was rinsed three times with phosphate buffered saline to remove unbound label. Radioactive label remaining in the sebocytes was harvested and counted using a TopCount- NXT brand scintillation counter (Packard Co., Meriden, Connecticut) .
  • TDCM iso-tridecyl carboxymethylate
  • TDCE iso-tridecyl carboxyethylate
  • This example provides carboxypropylation of an alcohol, which yields the corresponding alkyl oxy butyric acid with a purity of about 50% to about 70%.
  • Potassium tertiary-butoxide (9.42g, 0.084mole) was weighed out into a small round bottom flask under moisture free atmosphere (N 2 dry box) . To this was then added 25ml dry p- dioxane or THF and while stirring, a mixture of Exxal ® 13 alcohol (Branched alcohol with 13 carbons; 4.0g, 0.02mole) and 4- chlorobutyric acid (Aldrich Chemicals, 0.02mole) in 15ml dry THF was added. The heterogeneous reaction mixture was then stirred and heated at slight reflux overnight under N 2 . Heating was stopped and after cooling to room temperature the solids were filtered and washed with THF and suction dried to give 6.70g lightly coloured paste.
  • Exxal ® 13 alcohol Branched alcohol with 13 carbons; 4.0g, 0.02mole
  • 4- chlorobutyric acid Aldrich Chemicals, 0.02mole
  • the paste was dissolved in water and acidified with HCI and extracted with chloroform (3x100 ml in a separatory funnel) .
  • the chloroform was dried (MgS0 4 ) and after filtration, removal of chloroform (rotavap) yielded about 1.0 g of an oily liquid product.
  • H and C NMR's of the liquid product confirmed the structure of the desired C 13 H 27 OCH 2 CH 2 CH 2 CO 2 H product (acid form) .
  • This example provides a comparison of the relative activity of carboxyakylates of the present invention with other derivatives of alcohols, as well as the branched alcohols from which the carboxyalkylates of the present invention are derived.
  • TDCE compound 1
  • compound 4 the branched alcohol from which it is derived.
  • Compound 7 is at least about 10 times as active as the Compound 6 branched alcohol from which it is derived.
  • This example compares the colour of TDCM and TDCE, showing that TDCE has better colour characteristics.
  • the light absorbency of the TDCM and TDCE compounds was determined at wavelengths of 340-500 nm using a Molecular
  • C13 iso-alcohol (22.00 g, Exxal 13) was first reacted with Thionyl chloride (excess) to form the corresponding C13 isoalcohol chloride, C13 H27 CI, in 88% yield after distilation (according to procedure outlined in Org. Syn. Coll. Vol. 4, 333, 1963) .
  • the 3 -ethoxylated isoalcohol will be reacted with acrylonitril, followed by HCI, to form the corresponding carboxy-alkyl 3- ethoxylated isoalcohol, according to Examples 2 and 4.

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Abstract

L'invention concerne des méthodes cosmétiques de soins de beauté d'utilisation et d'élaboration de carboxyalkylates d'alcools ramifiés et/ou d'alkoxylates associés, des compositions renfermant lesdits composés, et leur procédé de production. Ces composés présentent la formule (A) : R-O-M, dans laquelle R représente une chaîne d'alcényle ou d'alkyle ramifiée possédant au moins 7 atomes de carbone et au moins deux branches, O représente un atome d'oxygène, M représente (-(CH2)p0)n- (CH2)MC02X, où n est égal à zéro ou est un nombre entier compris entre 1 et 7, m est un nombre entier compris entre 2 et 4, p est un nombre entier compris entre 2 et 4, et X représente l'hydrogène, un groupe méthyle, un groupe éthyle ou un cation. Ces composés et compositions permettent de réguler les sécrétions de sébum provenant des sébocytes, d'obtenir une régulation améliorée de l'huile et une meilleure sensation cutanée, de prévenir l'effet brillant et l'aspect collant, tandis qu'ils possèdent une activité antimicrobienne vis-à-vis des bactéries liées à l'acné ainsi que des actions bénéfiques anti-vieillissement qui se soldent par la diminution de l'apparition de rides et d'une peau âgée, un éclat, une clarté et un aspect superficiel cutanés améliorés, et une jeunesse et une santé retrouvées de la peau.
PCT/EP2003/007649 2002-07-17 2003-07-15 Compositions cosmetiques de soins de beaute contenant des carboxyalkylates d'alcools ramifies et/ou des alkoxylates associes WO2004006883A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2005505071A JP2005539093A (ja) 2002-07-17 2003-07-15 分枝状アルコールのカルボキシアルキレート及び／またはそのアルコキシレートを含有するスキンケア用化粧組成物
MXPA05000679A MXPA05000679A (es) 2002-07-17 2003-07-15 Composiciones cosmeticas para el cuidado de la piel que contienen carboxialquilatos de alcoholes ramificados y/o alcoxilatos de los mismos.
CN038170345A CN1668274B (zh) 2002-07-17 2003-07-15 包含支链醇的羧烷基化物和/或其烷氧基化物的皮肤护理美容组合物
AU2003254356A AU2003254356B2 (en) 2002-07-17 2003-07-15 Skin care cosmetic compositions containing carboxyalkylates of branched alcohols and/or alkoxylates thereof

Applications Claiming Priority (6)

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US10/196,881 US20040013630A1 (en) 2002-07-17 2002-07-17 Skin care cosmetic compositions containing carboxyalkylates of branched alcohols and/or alkoxylates thereof
US10/196,770 US6916851B2 (en) 2002-07-17 2002-07-17 Skin care cosmetic methods of sebum control using carboxyalkylates of branched alcohols and/or alkoxylates thereof
US10/196,770 2002-07-17
US10/196,881 2002-07-17
US41615702P 2002-10-04 2002-10-04
US60/416,157 2002-10-04

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009124750A1 (fr) * 2008-04-08 2009-10-15 Süd-Chemie AG Compositions solides adsorbant les odeurs, à base de ricinoléates de zinc, et composés apparentés

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA200609973B (en) * 2004-06-14 2008-06-25 Unilever Plc Method of decreasing sebum production and pore size
JP5718064B2 (ja) * 2011-01-07 2015-05-13 花王株式会社 抗真菌剤

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1920137A (en) * 1932-09-28 1933-07-25 Resinous Prod & Chemical Co Alkoxyacetic acids
US2870195A (en) * 1955-04-20 1959-01-20 Monsanto Chemicals Alkyl beta-alkoxypropionates
US3992443A (en) * 1974-04-17 1976-11-16 Chemische Werke Huls Aktiengesellschaft Process for the carboxymethylation of alcohols or ether alcohols
EP0846462A1 (fr) * 1996-11-07 1998-06-10 L'oreal Composition cosmétique sous la forme d'un gel transparent moussant
WO1999014180A1 (fr) * 1997-09-17 1999-03-25 Cognis Deutschland Gmbh Procede de preparation d'acides carboxyliques d'ether de couleur claire
WO1999055300A1 (fr) * 1998-04-23 1999-11-04 Unilever Plc Compositions de produits cosmetiques pour le soin de la peau
WO2002002067A1 (fr) * 2000-06-30 2002-01-10 Unilever Plc Compositions cosmetiques pour la peau contenant des carboxymethylates d'alcools ramifies et/ou des ethoxylates de ceux-ci

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Publication number Priority date Publication date Assignee Title
DE4112440C1 (fr) * 1991-04-16 1992-10-22 Diagen Institut Fuer Molekularbiologische Diagnostik Gmbh, 4000 Duesseldorf, De

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1920137A (en) * 1932-09-28 1933-07-25 Resinous Prod & Chemical Co Alkoxyacetic acids
US2870195A (en) * 1955-04-20 1959-01-20 Monsanto Chemicals Alkyl beta-alkoxypropionates
US3992443A (en) * 1974-04-17 1976-11-16 Chemische Werke Huls Aktiengesellschaft Process for the carboxymethylation of alcohols or ether alcohols
EP0846462A1 (fr) * 1996-11-07 1998-06-10 L'oreal Composition cosmétique sous la forme d'un gel transparent moussant
WO1999014180A1 (fr) * 1997-09-17 1999-03-25 Cognis Deutschland Gmbh Procede de preparation d'acides carboxyliques d'ether de couleur claire
WO1999055300A1 (fr) * 1998-04-23 1999-11-04 Unilever Plc Compositions de produits cosmetiques pour le soin de la peau
WO2002002067A1 (fr) * 2000-06-30 2002-01-10 Unilever Plc Compositions cosmetiques pour la peau contenant des carboxymethylates d'alcools ramifies et/ou des ethoxylates de ceux-ci

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009124750A1 (fr) * 2008-04-08 2009-10-15 Süd-Chemie AG Compositions solides adsorbant les odeurs, à base de ricinoléates de zinc, et composés apparentés

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JP2005539093A (ja) 2005-12-22
AU2003254356A1 (en) 2004-02-02
KR20050026961A (ko) 2005-03-16
CN1668274A (zh) 2005-09-14
WO2004006883A8 (fr) 2004-04-08
MXPA05000679A (es) 2005-03-31
CN1668274B (zh) 2010-06-16

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