EP1509195A1 - Sunscreen cosmetic compositions storage stabilized with malonate salts - Google Patents

Sunscreen cosmetic compositions storage stabilized with malonate salts

Info

Publication number
EP1509195A1
EP1509195A1 EP03730114A EP03730114A EP1509195A1 EP 1509195 A1 EP1509195 A1 EP 1509195A1 EP 03730114 A EP03730114 A EP 03730114A EP 03730114 A EP03730114 A EP 03730114A EP 1509195 A1 EP1509195 A1 EP 1509195A1
Authority
EP
European Patent Office
Prior art keywords
malonate
composition according
weight
salt
acid
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
EP03730114A
Other languages
German (de)
English (en)
French (fr)
Inventor
Joanna H. Unilever Home & Personal Care USA ZHANG
Joseph R. Unilever Home & Personal Care FARYNIARZ
Michael Ch. Unilever Home & Personal Care CHENEY
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.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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
Application filed by Unilever PLC, Unilever NV filed Critical Unilever PLC
Publication of EP1509195A1 publication Critical patent/EP1509195A1/en
Ceased legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0208Tissues; Wipes; Patches
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/046Aerosols; Foams
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362Polycarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/12Face or body powders for grooming, adorning or absorbing
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations

Definitions

  • the invention concerns sunscreen cosmetic compositions stabilized by malonate salts against decomposition during storage .
  • Sunscreen agents operate to shield human bodies from sun irradiation. Unfortunately, sunscreen agent upon occasion will discolor the cosmetic formulations into which they are blended.
  • a cosmetic composition which includes:
  • malonate salts may be useful for this invention. Many types of counter cations to the malonate anions may be utilized in forming the salts.
  • Malonate salts may either be the half or fully neutralized malonic acid or combinations thereof as represented by general formulas (I) and (II) :
  • X is a cationic counterion
  • Suitable inorganic cationic counterions include those of alkali and alkaline earth metals. Representative examples include the cations of lithium, sodium, potassium, magnesium, calcium, ammonium and combinations thereof.
  • quaternized nitrogen cations having from 1 to 1,000, preferably from 1 to 20, and optimally from 3 to 12 carbon atoms.
  • Illustrative are those cations derived from amines which include polyethyleneimine, triethanolamine, diethanolamine, propanolamine, monoethanolamine, methylamine, ethylamine, propylamine, isopropylamine, butylamine, isobutylamine, t-butylamine, pentylamine, isopentylamine, hexylamine, cyclohexylamine, cyclopentylamine, norbornylamine, octylamine, ethylhexylamine, nonylamine, decylamine, pyrrolidone, amino acids (lysine, alamine, glutamine, histidine, glycine) , 2- amino-2 -methyl -1-propanol , dimethyl
  • Preferred salts include ammonium malonate, diammonium malonate, dimethylethanolammonium malonate, bis (dimethylethanolammonium) malonate, tris (hydroxymethyl) methane ammonium, malonate, and di [tris (hydroxymethyl) methane ammonium] malonate .
  • Amounts of the malonic acid salt may range from about 0.0001% to about 30%, preferably from about 0.1% to about 15%, more preferably from about 0.5% to about 10%, optimally from about 1% to about 8% by weight of the cosmetic composition.
  • the present invention can utilize as the active ingredient salt I, salt II or mixtures of these salts.
  • the molar ratio of mono-salt I to di-salt II may range from about 1000:1 to about 1:1000, preferably from about 10:1 to about 1:500, more preferably from about 2:1 to about 1:200, optimally from about 1:1 to about 1:20.
  • Sunscreen agents formulated into compositions of the present invention are those organic substances having a chromophoric group active within the ultraviolet radiation range from 280 to 400 nm.
  • Chromophoric functionalized organic sunscreen agents may be divided into the following categories (with specific examples), including: p-Aminobenzoic acid, its salts and its derivatives (ethyl, isobutyl, glyceryl esters; p-dimethylaminobenzoic acid); Anthranilates (o-aminobenzoates; methyl, menthyl , phenyl , benzyl, phenylethyl, linalyl, terpinyl, and cyclohexenyl esters); Salicylates (octyl, amyl , phenyl, benzyl, menthyl, glyceryl, and dipropyleneglycol esters); Cinnamic acid derivatives (menthyl and benzyl esters, al
  • 2-ethylhexyl p-methoxycinnamate 4, ' -t-butyl methoxydibenzoylmethane, 2-hydroxy-4- methoxybenzophenone, octyldimethyl p-aminobenzoic acid, digalloyltrioleate, 2 , 2 -dihydroxy-4 -methoxybenzophenone, ethyl 4- [bis (hydroxypropyl) ] aminobenzoate, 2-ethylhexyl -2- cyano-3 , 3-diphenylacrylate, 2-ethylhexylsalicylate, glycerol p-aminobenzoate, 3,3, 5-trimethylcyclohexylsalicylate, methylanthranilate, p-dimethylaminobenzoic acid or aminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, 2- pheny
  • Suitable commercially available organic sunscreen agents are those identified under the following table.
  • Particularly discoloration promoting materials are UNA type of sunscreens, the most evident of which is 4, 4'-t- butylmethoxydibenzoylmethane available commercially as
  • Amounts of the aforementioned sunscreen agents will generally range from about 0.05% to about 40%, preferably from about 1% to about 30%, more preferably from about 2% to about 15%, optimally from about 4% to about 10% by weight.
  • Compositions of this invention will also include a cosmetically acceptable carrier. Amounts of the carrier may range from 1% to 99.9%, preferably from about 70% to about 95%, optimally from about 80% to about 90%.
  • the useful carriers are water, emollients, fatty acids, fatty alcohols, humectants, thickeners and combinations thereof.
  • the carrier may be aqueous, anhydrous or an emulsion.
  • the compositions are aqueous, especially water and oil emulsions of the W/O or O/W variety. Water when present may be in amounts ranging from about 5% to about
  • Emollient materials may serve as cosmetically acceptable carriers. These may be in the form of silicone oils, synthetic esters and hydrocarbons. Suitable amounts of the emollients may range anywhere from about 0.1% to about 95%, preferably between about 1% and about 50% 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 (cyclomethicone) or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms.
  • 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 x 10 to 0.1 m /s at 25°C.
  • preferred non-volatile emollients useful in the present compositions are the preferred non-volatile emollients.
  • polydimethyl siloxanes having viscosities from about 1 x 10 to about 4 x 10 "4 m 2 /s at 25°C.
  • Nonvolatile silicones are emulsifying and non-emulsifying silicone elastomers. Representative of this category is Dimethicone/Vinyl Dimethicone Crosspolymer available as Dow Corning 9040, General Electric SFE 839, and Shin-Etsu KSG-18. Silicone waxes such as Silwax WS-L (Dimethicone Copolyol Laurate) may also be useful .
  • ester emollients are:
  • Alkenyl or alkyl esters of fatty acids having 10 to 20 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 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl mono-stearate, 1,3-butylene glycol monostearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters. Particularly useful are pentaerythritol, trimethylolpropane and neopentyl glycol
  • Wax esters such as beeswax, spermaceti wax and tribehenin wax.
  • Sterols esters of which cholesterol fatty acid esters are examples thereof.
  • Hydrocarbons which are suitable cosmetically acceptable carriers include petrolatum, mineral oil, C11-C 1 3 isoparaffins, polyalphaolefins, and especially isohexadecane, available commercially as Permethyl 101A from Presperse Inc .
  • Fatty acids having from 10 to 30 carbon atoms may also be suitable as cosmetically acceptable carriers.
  • Illustrative of this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachidic, behenic and erucic acids.
  • Fatty alcohols having from 10 to 30 carbon atoms are another useful category of cosmetically acceptable carrier.
  • Illustrative of this category are stearyl alcohol, lauryl alcohol, myristyl alcohol and cetyl alcohol.
  • Humectants of the polyhydric alcohol -type can be employed as cosmetically acceptable carriers.
  • 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, isoprene glycol, 1 , 2 , 6-hexanetriol , ethoxylated glycerol, propoxylated glycerol and mixtures thereof.
  • the amount of humectant may range anywhere from 0.5% to 50%, preferably between 1% and 15% by weight of the composition.
  • Thickeners can be utilized as part of the cosmetically acceptable carrier of compositions according to the present invention.
  • Typical thickeners include crosslinked acrylates
  • cellulosic derivatives and natural gums.
  • useful cellulosic derivatives are sodium carboxymethylcellulose, hydroxypropyl methocellulose, 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.
  • Inorganics may also be utilized as thickeners, particularly clays such as bentonites and hectorites, fumed silicas, and silicates such as magnesium aluminum silicate
  • Amounts of the thickener may range from 0.0001% to 10%, usually from 0.001% to 1%, optimally from 0.01% to 0.5% by weight .
  • Cosmetic compositions of the present invention may be in any form. These forms may include lotions, creams, roll -on formulations, sticks, mousses, aerosol and non-aerosol sprays and fabric (e.g. nonwoven textile) -applied formulations .
  • Surfactants may also be present in cosmetic compositions of the present invention. Total concentration of the surfactant when present may range from about 0.1% to about 40%, preferably from about 1% to about 20%, optimally from about 1% to about 5% by weight of the composition.
  • the surfactant may be selected from the group consisting of anionic, nonionic, cationic and amphoteric actives. Particularly preferred nonionic surfactants are those with a
  • alkylene oxide 20 moles of alkylene oxide; mono- and di-fatty acid esters of ethylene glycol; fatty acid monoglyceride ; sorbitan, mono- and di- C 8 -C 2 o fatty acids; and polyoxyethylene sorbitan as well as combinations thereof.
  • Alkyl polyglycosides and saccharide fatty amides are also suitable nonionic surfactants.
  • Preferred anionic surfactants include soap, alkyl ether sulfates and sulfonates, alkyl sulfates and sulfonates, alkylbenzene sulfonates, alkyl and dialkyl sulfosuccinates,
  • Preservatives can desirably be incorporated into the cosmetic compositions of this invention to protect against the growth of potentially harmful microorganisms.
  • Suitable traditional preservatives for compositions of this invention are alkyl esters of para-hydroxybenzoic acid.
  • Other preservatives which have more recently come into use include hydantoin derivatives, propionate salts, and a variety of quaternary ammonium compounds.
  • Cosmetic chemists are familiar with appropriate preservatives and routinely choose them to satisfy the preservative challenge test and to provide product stability.
  • Particularly preferred preservatives are phenoxyethanol , methyl paraben, propyl paraben, imidazolidinyl urea, sodium dehydroacetate and benzyl alcohol.
  • the preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients in the emulsion. Preservatives are preferably employed in amounts ranging from 0.01% to 2% by weight of the composition.
  • compositions of the present invention may include vitamins.
  • Illustrative vitamins are Vitamin A (retinol), Vitamin B 2 ,
  • Vitamin Bg Vitamin C, Vitamin E and Biotin.
  • Derivatives of the vitamins may also be employed.
  • Vitamin C derivatives include ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate and ascorbyl glycoside.
  • Derivatives of Vitamin E include tocopheryl acetate, tocopheryl palmitate and tocopheryl linoleate. DL-panthenol and derivatives may also be employed.
  • Total amount of vitamins when present in compositions according to the present invention may range from 0.001% to 10%, preferably from 0.01% to 1%, optimally from 0.1% to 0.5% by weight.
  • Another type of useful substance can be that of an enzyme such as oxidases, proteases, lipases and combinations.
  • superoxide dismutase commercially available as Biocell SOD from the Brooks Company, USA.
  • Skin lightening compounds may be included in the compositions of the invention.
  • Illustrative substances are placental extract, lactic acid, niacinamide, arbutin, kojic acid, ferulic acid, resorcinol and derivatives including 4- substituted resorcinols and combinations thereof. Amounts of these agents may range from about 0.1% to about 10%, preferably from about 0.5& to about 2% by weight of the composition.
  • Desquamation promoters may be present.
  • Illustrative are the alpha-hydroxycarboxylic acids and beta-hydroxycarboxylic acids.
  • the term "acid” is meant to include not only the free acid but also salts and C 1 -C 30 alkyl or aryl esters thereof and lactones generated from removal of water to form cyclic or linear lactone structures.
  • Representative acids are glycolic, lactic and malic acids.
  • Salicylic acid is representative of the beta-hydroxycarboxylic acids. Amounts of these materials when present may range from about 0.1% to about 15% by weight of the composition.
  • compositions of this invention may optionally be included in compositions of this invention.
  • Illustrative are green tea, chamomile, licorice and extract combinations thereof.
  • the extracts may either be water soluble or water- insoluble carried in a solvent which respectively is hydrophilic or hydrophobic. Water and ethanol are the preferred extract solvents .
  • ceramides including Ceramide 1, Ceramide 3, Ceramide 3B and Ceramide 6 as well as pseudoceramides may also be utilized but in many compositions of the present invention these ceramides and pseudoceramides may also be excluded. Amounts of these materials may range from about 0.000001% to about 10%, preferably from about 0.0001% to about 1% by weight.
  • compositions of the present invention may also be included in compositions of the present invention.
  • Each of these substances may range from about 0.05% to about 5%, preferably between 0.1% and 3% by weight.
  • a typical cosmetic cream according to the present invention is outlined under Table II.
  • a water-in-oil topical liquid make-up foundation utilizing the malonate salts for color stabilization of the present invention is described in Table III below.
  • Illustrated herein is a skin cream incorporating for color stabilization the malonate salts of the present invention.
  • a relatively anhydrous composition according to the present invention is reported in Table VI .
  • An aerosol packaged foaming cleanser suitable for the present invention is outlined in Table VII.
  • An aerosol is prepared using 92% by weight of the concentrate in Table VI and 8% propellant, the latter being a combination of dimethylether, isobutane and propane.
  • An adhesive cosmetic patch may also be formulated according to the present invention.
  • An adhesive hydrogel is prepared by mixing 30 grams of 2-acrylamido-2-methylpropane sulphonic acid monomer in 20 grams distilled water and 5 grams of a 1% aqueous solution of methylene-bis-acrylamide . The solution is then activated with 0.4% magnesium persulphate catalyst. Shortly after mixing the catalyst with the hydrogel solution, 0.1 grams ammonium malonate and 0.05 grams Parsol
  • a disposable, single use personal towelette product is described according to the present invention.
  • a 70/30 polyester/rayon non-woven towelette is prepared with a weight of 1.8 grams and dimensions of 15cm by 20cm. Onto this towelette is impregnated a composition as outlined in Table VIII below.
  • Test conditions included ovens kept at 22°C, 37°C, 40°C, 50°C and 60°, for evaluating thermal stability.
  • the test conditions also included stations wherein the formulas were exposed to natural (northern) light and fluorescent light at room temperature, to evaluate light stability.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
EP03730114A 2002-05-29 2003-05-22 Sunscreen cosmetic compositions storage stabilized with malonate salts Ceased EP1509195A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US38383702P 2002-05-29 2002-05-29
US383837P 2002-05-29
US45533203P 2003-03-17 2003-03-17
US455332P 2003-03-17
PCT/EP2003/005480 WO2003099250A1 (en) 2002-05-29 2003-05-22 Sunscreen cosmetic compositions storage stabilized with malonate salts

Publications (1)

Publication Number Publication Date
EP1509195A1 true EP1509195A1 (en) 2005-03-02

Family

ID=29587037

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03730114A Ceased EP1509195A1 (en) 2002-05-29 2003-05-22 Sunscreen cosmetic compositions storage stabilized with malonate salts

Country Status (10)

Country Link
EP (1) EP1509195A1 (es)
JP (1) JP2005532328A (es)
KR (1) KR20050004248A (es)
CN (1) CN1671352A (es)
AR (1) AR039910A1 (es)
AU (1) AU2003240711A1 (es)
CA (1) CA2486882A1 (es)
MX (1) MXPA04011905A (es)
TW (1) TW200406227A (es)
WO (1) WO2003099250A1 (es)

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Publication number Priority date Publication date Assignee Title
US20040202689A1 (en) * 2003-03-17 2004-10-14 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Terpenoid fragrance components stabilized with malonic acid salts
DE602004006845T2 (de) * 2003-03-17 2008-02-28 Unilever N.V. Vefahren zur Überwindung von eingewachsenen Haaren
US7285262B2 (en) * 2003-07-11 2007-10-23 Tanning Research Laboratories, Inc. Natural sunlight photostable composition
US7404949B2 (en) 2004-03-15 2008-07-29 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Methods and compositions useful to prevent in-grown hair arising from shaving
DE102005038069A1 (de) 2005-08-10 2007-03-08 Henkel Kgaa Öl-in-Wasser Emulsionen
DE102006061829A1 (de) * 2006-12-21 2008-06-26 Henkel Kgaa Vorbehandlungsmittel zum Schutz der Kopfhaut
US8088364B2 (en) * 2009-03-20 2012-01-03 The Procter & Gamble Company Personal-care composition comprising oil-soluble solid sunscreens
NZ596292A (en) 2009-04-28 2014-04-30 Proteus Digital Health Inc Highly reliable ingestible event markers and methods for using the same
WO2015112603A1 (en) 2014-01-21 2015-07-30 Proteus Digital Health, Inc. Masticable ingestible product and communication system therefor
JP2016508529A (ja) 2013-01-29 2016-03-22 プロテウス デジタル ヘルス, インコーポレイテッド 高度に膨張可能なポリマーフィルムおよびこれを含む組成物
US9796576B2 (en) 2013-08-30 2017-10-24 Proteus Digital Health, Inc. Container with electronically controlled interlock
JP6370589B2 (ja) * 2014-04-24 2018-08-08 ポーラ化成工業株式会社 水中油乳化組成物
EP3840574A4 (en) * 2018-09-27 2022-06-22 Arxada, LLC STABLE COLOR PRESERVATION COMPOSITION

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JPH064529B2 (ja) * 1985-03-20 1994-01-19 株式会社資生堂 皮膚外用剤
JP3299054B2 (ja) * 1994-10-19 2002-07-08 花王株式会社 皮膚化粧料
FR2760464B1 (fr) * 1997-03-07 2005-07-01 Oreal Procede pour ameliorer la photostabilite d'un derive de dibenzoylmethane par un silane, benzalmalonate, procede de preparation de silanes benzalmalonates
EP1262166A1 (de) * 2001-06-01 2002-12-04 Cognis France S.A. Kosmetische und/oder pharmazeutische Zubereitungen enthaltend einen Extrakt aus Pterocarpus marsupium

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Also Published As

Publication number Publication date
WO2003099250A1 (en) 2003-12-04
KR20050004248A (ko) 2005-01-12
CN1671352A (zh) 2005-09-21
AU2003240711A1 (en) 2003-12-12
TW200406227A (en) 2004-05-01
AR039910A1 (es) 2005-03-09
MXPA04011905A (es) 2005-03-31
JP2005532328A (ja) 2005-10-27
CA2486882A1 (en) 2003-12-04

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