WO1994009756A1 - Retinol containing cosmetic composition - Google Patents

Retinol containing cosmetic composition Download PDF

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Publication number
WO1994009756A1
WO1994009756A1 PCT/EP1993/003064 EP9303064W WO9409756A1 WO 1994009756 A1 WO1994009756 A1 WO 1994009756A1 EP 9303064 W EP9303064 W EP 9303064W WO 9409756 A1 WO9409756 A1 WO 9409756A1
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WO
WIPO (PCT)
Prior art keywords
skin
composition
derivatives
retinol
weight
Prior art date
Application number
PCT/EP1993/003064
Other languages
English (en)
French (fr)
Inventor
Clive Roderick Harding
Caroline Marian Lee
Ian Richard Scott
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10724621&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1994009756(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Unilever Plc, Unilever Nv filed Critical Unilever Plc
Priority to JP6510720A priority Critical patent/JPH08502742A/ja
Priority to AU54201/94A priority patent/AU680844B2/en
Priority to BR9307375-5A priority patent/BR9307375A/pt
Priority to KR1019950701783A priority patent/KR950703928A/ko
Priority to EP93924575A priority patent/EP0666735B1/en
Priority to DE69321479T priority patent/DE69321479T2/de
Priority to CA002147262A priority patent/CA2147262A1/en
Publication of WO1994009756A1 publication Critical patent/WO1994009756A1/en
Priority to HK98115576A priority patent/HK1014238A1/xx

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Classifications

    • 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
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • 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
    • A61K8/347—Phenols
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • A61K8/355—Quinones
    • 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
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/60—Sugars; 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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/673—Vitamin B group
    • A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A61K8/981—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of mammals or bird
    • A61K8/982—Reproductive organs; Embryos, Eggs
    • 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
    • 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
    • A61Q19/004—Aftersun 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
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • the invention relates to a composition for topical application to human skin in order to lighten skin colour and to promote the repair of photo-damaged skin and/or to reduce or prevent the damaging effects of ultra-violet light on skin.
  • the invention also relates to the use of such compositions in lightening skin colour, in the repair of photo-damaged skin and in the prevention of damage to skin due to exposure to ultra-violet light.
  • Skin blotchiness or mottling is due to changes in the melanocytes or the processing of melanin within the population of epidermal cells.
  • These pigment producing cells which unlike the keratinocytes remain at the base of the epidermis, lose their normal regulation process with ageing and produce excess pigment. This leads to the formation of dense perinuclear clumps of melanin in slowly turning over keratinocytes within the epidermis, and areas of hyperpigmentation or 'age spots' develop.
  • certain skin lightening agents such as kojic acid, hydroquinone or ascorbic acid are effective by inhibiting the formation of melanin.
  • Vitamin A acid retinoic acid
  • Vitamin A acid is beneficial in hyperpigmentation problems by normalising the skin colour.
  • Vitamin A acid prevents accumulation of pigment within the more rapidly dividing and migrating keratinocytes. Vitamin A acid also enhances the pigment reducing potential of conventional skin lightening agents.
  • Vitamin A acid is a potent skin irritant, and can accordingly damage the skin.
  • Vitamin A acid is also a teratogen. Its recommended use for example as a prescription drug in the treatment of acne involves careful control, such that excessive doses are avoided in order to restrict the side effects which can occur with skin.
  • Vitamin A acid for lightening skin and in the treatment or prevention of photo-damaged skin is severely limited by these side effects, and for this reason it is not generally recommended for use in cosmetic products.
  • retinol or certain derivatives thereof when combined with a skin lightening agent can be used effectively in the repair of photo-damaged skin or the prevention of photo-damage to skin following exposure to ultra-violet light. This combination is also particularly useful in reducing hyperpigmentation of skin.
  • the invention is accordingly concerned with compositions comprising retinol or certain derivatives thereof together with a skin lightening agent for topical application to human skin, and the use of this combination of active agents to lighten skin and in the treatment of photo- damaged and/or hyperpigmented skin or the prevention thereof, following excessive exposure to ultra-violet light.
  • the invention provides a composition suitable for topical application to human skin in order to lighten skin and promote repair of photo-damaged skin and/or to reduce or prevent the damaging effects of ultra-violet light on skin, which composition comprises:
  • X represents H or COR where R represents a group chosen from branched or unbranched, alkyl or alkenyl groups having an average of from 1 to 20 carbon atoms;
  • a skin lightening agent chosen from L-ascorbic acid and derivatives thereof, kojic acid and derivatives thereof, hydroquinone and derivatives thereof, extract of placenta, arbutin, niacin, niacinamide, ⁇ hydroxy acids, phloretin, phloridzin, liquorice extract, cysteaminylphenol and derivatives thereof and compounds having the structure (2) :
  • R 1 represents H, or an ether group represented by OR 3 ,
  • R 2 and R 3 are the same or different and each represents a group chosen from branched or unbranched alkyl or alkenyl groups having an average of from 1 to 20 carbon atoms.
  • Invention concerns a composition
  • a composition comprising retinol or a derivative thereof together with a skin lightening agent which together behave synergistically in lightening skin and reducing skin blotchiness and mottling due to hyperpigmentation.
  • a skin lightening agent which together behave synergistically in lightening skin and reducing skin blotchiness and mottling due to hyperpigmentation.
  • co-formulation with a sunscreen will enhance the photo stability and activity of retinol or its derivative within the formulation and also prevent further actinic damage to the skin.
  • composition according to the invention comprises retinol or a derivative thereof having the structure (1) .
  • examples of derivatives of retinol include:
  • the amount of retinol, or a derivative thereof, present in the composition according to the invention is from 0.001 to 10% and preferably 0.01 to 5% by weight of the composition.
  • the composition comprises retinol, most preferably the composition comprises the trans-isomer of retinol.
  • the skin lightening agent is the skin lightening agent
  • composition according to the invention also comprises a skin lightening agent.
  • Examples of skin lightening agents include:
  • Extract of placenta Compounds having the structure (2) Arbutin a hydroxy acids phloretin phloridzin, liquorice extract cysteaminylphenol and derivatives thereof
  • the skin lightening agent is hydroquinone and derivatives thereof, most preferably hydroquinone.
  • the amount of skin lightening agent which is present in the composition according to the invention is from 0.01 to 20%, preferably 0.1 to 10% by weight of the composition.
  • composition according to the invention also comprises a cosmetically acceptable vehicle to act as a dilutant, dispersant or carrier for other materials present in the composition, so as to facilitate their distribution when the composition is applied to the skin.
  • Vehicles other than water can include liquid or solid emollients, solvents, humectants, thickeners and powders. Examples of each of these types of vehicle, which can be used singly or as mixtures of one or more vehicles, are as follows:
  • Emollients such as stearyl alcohol, glyceryl monoricinoleate, mink oil, cetyl alcohol, isopropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, eicosanyl alcohol, behenyl alcohol, cetyl palmitate, silicone oils such as dimethylpolysiloxane, di-n-butyl sebacate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, butyl stearate, polyethylene glycol, triethylene glycol, lanolin, cocoa butter, corn oil, cotton seed oil, olive oil, palm kernel oil, rapeseed oil, safflower seed oil, evening primrose oil, soybean oil,
  • Propellants such as propane, butane, isobutane, dimethyl ether, carbon dioxide, nitrous oxide;
  • Solvents such as ethyl alcohol, isopropanol, acetone, ethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether;
  • Powders such as chalk, talc, fullers earth, kaolin, starch, gums, colloidal silica sodium polyacrylate, tetra alkyl and/or trialkyl aryl ammonium smectites, chemically modified magnesium aluminium silicate, organically modified montmorillonite clay, hydrated aluminium silicate, fumed silica, carboxyvinyl polymer, sodium carboxymethyl cellulose, ethylene glycol monostearate.
  • the cosmetically acceptable vehicle will usually form from 10 to 99.9%, preferably from 50 to 99% by weight of the emulsion, and can, in the absence of other cosmetic adjuncts, form the balance of the emulsion.
  • composition of the invention optionally can comprise an organic sunscreen further to enhance the benefit of the composition in providing protection from the harmful effects of excessive exposure to sunlight.
  • organic sunscreens when required, include those set out in Table 1 below, and mixtures thereof.
  • composition of the invention can accordingly comprise from 0.1 to 10%, preferably from 1 to 5% by weight of an organic sunscreen material.
  • composition according to the invention optionally can also comprise as a sunscreen ultrafine titanium dioxide in either of two forms, namely water-dispersible titanium dioxide and oil-dispersible titanium dioxide.
  • Water-dispersible titanium dioxide is ultrafine titanium dioxide, the particles of which are uncoated or which are coated with a material to impart a hydrophilic surface property to the particles.
  • a material to impart a hydrophilic surface property examples include aluminium oxide and aluminium silicate.
  • Oil-dispersible titanium dioxide is ultrafine titanium dioxide, the particles of which exhibit a hydrophobic surface property, and which, for this purpose, can be coated with metal soaps such as aluminium stearate, aluminium laurate or zinc stearate, or with organosilicone compounds.
  • ultra titanium dioxide particles of titanium dioxide having an average particle size of less than lOOnm, preferably from 10 to 40nm and most preferably from 15 to 25nm.
  • the weight ratio of water-dispersible titanium dioxide to oil-dispersible titanium dioxide should be from 1:4 to 4:1, preferably from 1:2 to 2:1 and ideally about equal weight proportions.
  • the total amount of titanium dioxide that can optionally can be incorporated in the composition according to the invention is from 1 to 25%, preferably from 2 to 10% and ideally from 3 to 7% by weight of the composition.
  • the emulsion of the invention optionally can comprise an inorganic sunscreen in addition to ultrafine titanium dioxide as herein defined.
  • examples of other inorganic sunscreens include: zinc oxide, having an average particle size of from 1 to 300nm,
  • iron oxide having an average particle size of from 1 to 300nm
  • silica such as fumed silica, having an average particle size of from 1 to lOOnm.
  • silica when used as an ingredient in the emulsion according to the invention can provide protection from infra-red radiation.
  • composition according to the invention is an emulsion, in which case an oil or oily material will normally 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-lyophilic balance (HLB) of the emulsifier employed.
  • HLB hydrophilic-lyophilic balance
  • composition according to the invention can optionally comprise one or more oils or other materials having the properties of an oil.
  • oils examples include mineral oil and vegetable oils, and oil materials, such as those already proposed herein as emollients.
  • oils or oily materials include silicone oils, both volatile and non-volatile, such as polydimethyl siloxanes.
  • the oil or oily material when present for the purposes for forming an emulsion, will normally form up to 90%, preferably from 10 to 80% by volume of the composition.
  • composition according to the invention can also optionally comprise one or more emulsifiers the choice of which will normally determine whether a water-in-oil or and oil-in-water emulsion is formed.
  • the chosen emulsifier or emulsifiers should normally have an average HLB value of from 1 to 6.
  • a chosen emulsifier or emulsifiers should have an average HLB value of >6.
  • Suitable emulsifiers are set below in Table 1 in which the chemical name of the emulsifiers is given together with an example of a trade name as commercially available, and the average HLB value.
  • Sorbitan trioleate Arlacel 85 1.8 Sorbitan tristearate Span 65 2.1 Glycerol monooleate Aldo MD 2.7 Glycerol monostearate At ul 84S 2.8 Glycerol monolaurate Aldo MC 3.3 Sorbitan sesquioleate Arlacel 83 3.7 Sorbitan monooleate Arlacel 80 4.3 Sorbitan monostearate Arlacel 60 4.7 Poloxyethylene (2) stearyl ether Brij 72 4.9 Poloxyethylene sorbitol beeswax derivative PEG 200 dilaurate Sorbitan monopalmitate Polyoxyethylene (3.5) nonyl phenol PEG 200 monostearate
  • emulsifiers are not intended to be limiting and merely exemplifies selected emulsifiers which are suitable for use in accordance with the invention. It is to be understood that two or more emulsifiers can be employed if desired.
  • the amount of emulsifier or mixtures thereof, that optionally can be incorporated in the composition of the invention is from 1 to 50%, preferably from 2 to 20% and most preferably from 2 to 10% by weight of the composition.
  • composition of the invention can also comprise water, usually up to 80%, preferably from 5 to 80% by volume.
  • composition of the invention can also optionally comprise a high molecular weight silicone surfactant which can also act as an emulsifier, in place of or in addition to the optional emulsifier(s) already mentioned.
  • a high molecular weight silicone surfactant which can also act as an emulsifier, in place of or in addition to the optional emulsifier(s) already mentioned.
  • the silicone surfactant is a high molecular weight polymer of dimethyl polysiloxane with polyoxyethylene and/or polyoxypropylene side chains having a molecular weight of from 10,000 to 50,000 and having the structure:
  • CH CH
  • a has a value of from 9 to 115
  • b has a value of from 0 to 50
  • x has a value of from 133 to 673
  • y has a value of from 25 to 0.25.
  • the dimethyl polysiloxane polymer is one in which:
  • a has a value of from 10 to 114 b has a value of from 0 to 49 x has a value of from 388 to 402 y has a value of from 15 to 0.75
  • groups R 1 and R" being lauryl, and the other having a molcular weight of from 1000 to 5000.
  • a particularly preferred dimethyl polysiloxane polymer is one in which:
  • the dimethyl polysiloxane polymer is conveniently provided as a dispersion in a volatile siloxane, the dispersion comprising, for example, from 1 to 20% by volume of the polymer and from 80 to 99% by volume of the volatile siloxane.
  • the dispersion consists of a 10% by volume of the polymer dispersed in the volatile siloxane.
  • Examples of the volatile siloxanes in which the polysiloxane polymer can be dispersed include polydimethyl siloxane (pentamer and/or hexamer) .
  • a particularly preferred silicone surfactant is cyclomethicone and dimethicone copolyol, such as DC 3225C Formulation Aid available from DOW CORNING.
  • Another is laurylmethicone copolyol, such as DC Q2-5200, also available from Dow Corning.
  • the amount of silicone surfactant, when present in the composition will normally be up to 25%, preferably from 0.5 to 15% by weight of the emulsion.
  • adjuncts examples include preservatives, such as para-hydroxy benzoate esters; antioxidants, such butyl hydroxy toluene; humectants, such as glycerol, sorbitol, 2-pyrrolidone-5- carboxylate, dibutylphthalate, gelatin, polyethylene glycol, such as PEG 200-600; buffers, such as lactic acid together with a base such as triethanolamine or sodium hydroxide; waxes, such as beeswax, ozokerite wax, paraffin wax; plant extracts, such as Aloe vera, cornflower, witch hazel, elderflower, cucumber; thickeners; activity enhancers; colourants; and perfumes.
  • Cosmetic adjuncts can form the balance of the composition.
  • the composition according to the invention is intended primarily as a skin care product for topical application to human skin to lighten skin and/or to repair photo-damaged skin and to prevent photo-damage to skin due to exposure to sunlight.
  • the composition can be used to reduce skin blotchiness and mottling due to hyperpigmentation, to improve skin texture with reductions in fine wrinkling and otherwise to improve skin colour.
  • the composition when topically applied to skin, is useful in the prevention of actinic damage to all epidermal cells.
  • a small quantity of the composition for example from 1 to 5ml, 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 topical skin treatment composition of the invention can be formulated as a lotion having a viscosity of from 4,000 to 10,000 mPas, a fluid cream having a viscosity of from 10,000 to 20,000 mPas or a cream having a viscosity of from 20,000 to 100,000 mPas, or above.
  • 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 propellant-driven aerosol device or a container fitted with a pump suitable for finger operation.
  • the composition When 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.
  • Pigment producing cells derived from a mammalian melanoma are grown in culture by standard methods.
  • Preferred cell lines are B16 or S-91 cells, but other lines or primary mouse or human melanocytes can be used.
  • Melanoma cells are grown in cell culture medium such as RPMI 1640 (GIBCO) supplemented with fetal calf serum and glutamine to approximately 1/3 confluence.
  • the active is dissolved in culture medium, the pH adjusted as required and sterile filtered. The solution is then added to the cells.
  • the cells are cultured for a further period of 4 days and the amount of melanin produced assayed by measuring the absorbance at 540 nm of the melanin released into the medium.
  • the cells are incubated in 50 ⁇ g/ l neutral red solution for 3 hours at 37°C in 5% C0 2 in air.
  • the solution is aspirated, the cells washed once in saline and to them added a solvent (50% H 2 0, 49% ethanol, 1% acetic acid) to solubilise the dye.
  • the amount of neutral red dye is quantified by measuring absorbance at 540 nm.
  • compositions of skin lightening agents at a range of concentrations
  • retinol at a range of concentrations
  • compositions were compared with compositions having retinol alone at a range of concentrations and skin lightening agents alone at a range of concentrations.
  • results for both viability and melanin production were calculated as percentages of the control which contained medium alone. Results are given in Table 3 and 4.
  • the invention is further illustrated by the following examples; in each formulation, the titanium dioxide employed was ultrafine titanium dioxide having a mean particle size of from 15 to 25nm.
  • Example 1 in each formulation, the titanium dioxide employed was ultrafine titanium dioxide having a mean particle size of from 15 to 25nm.
  • This example illustrates a lotion according to the invention.
  • retinyl propionate 1 kojic acid 1 silicone surfactant 10 volatile siloxane 14 mineral oil 1.5 titanium dioxide (water-dispersible) 2.5 titanium dioxide (oil-dispersible) 2.5 2-hydroxy octanoic acid 1
  • This example illustrates a fluid cream according to the invention.
  • Parsol MCX octyl methoxycinnamate 3 titanium dioxide (oil-dispersible) 2 titanium dioxide (water-dispersible) 2 sodium chloride 2 butylene glycol 10
  • This example illustrates a cream according to the invention.
  • Parsol MCX octyl methoxycinnamate 1.5 titanium dioxide (oil-dispersible) 1.0 titanium dioxide (water-dispersible) 1
  • This example illustrates a lotion according to the invention.
  • This example illustrates a sunscreen cream in accordance with the invention.
  • This example also illustrates sunscreen cream in accordance with the invention.
  • retinyl acetate 0.2 retinyl laurate 2 niacin 2 cetyl dimethicone copolyol cetyl dimethicone polyglycery1-3-oleate hexyl laurate )
  • This example illustrates a lotion according to the invention.
  • This example illustrates a lotion according to the invention.
  • This example illustrates a lotion according to the invention.
  • retinyl octanoate 1 retinyl linoleate 1 phloridzin 1 silicone surfactant 10 volatile siloxane 14 mineral oil 1.5 ultrafine titanium dioxide (water-dispersible) 2.5 ultrafine titanium dioxide
  • This example illustrates an anhydrous formulation in accordance with the invention.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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PCT/EP1993/003064 1992-11-05 1993-11-02 Retinol containing cosmetic composition WO1994009756A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
JP6510720A JPH08502742A (ja) 1992-11-05 1993-11-02 レチノール含有化粧品組成物
AU54201/94A AU680844B2 (en) 1992-11-05 1993-11-02 Retinol containing cosmetic composition
BR9307375-5A BR9307375A (pt) 1992-11-05 1993-11-02 Composição adequada para aplicação tópica à pele humana e processo de reduzir ou impedir os efeitos de danos de luz uv à pele e/ou clarear a pele
KR1019950701783A KR950703928A (ko) 1992-11-05 1993-11-02 레티놀 함유 화장품 조성물(Retinol Containing Cosmetic Composition)
EP93924575A EP0666735B1 (en) 1992-11-05 1993-11-02 Retinol containing cosmetic composition
DE69321479T DE69321479T2 (de) 1992-11-05 1993-11-02 Retinol enthaltende kosmetische zusammensetzung
CA002147262A CA2147262A1 (en) 1992-11-05 1993-11-02 Retinol containing cosmetic composition
HK98115576A HK1014238A1 (en) 1992-11-05 1998-12-24 Retinol containing cosmetic composition

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GB929223235A GB9223235D0 (en) 1992-11-05 1992-11-05 Cosmetic composition
GB9223235.4 1992-11-05

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FR2715844A1 (fr) * 1994-02-04 1995-08-11 Oreal Emulsion contenant de l'acide ascorbique stabilisé, procédé de traitement cosmétique la mettant en Óoeuvre, ses utilisations.
WO1996017589A1 (en) * 1994-12-08 1996-06-13 Kao Corporation Method of smoothing or removing wrinkles and method of stimulating collagen synthesis
JPH08245362A (ja) * 1995-03-08 1996-09-24 Seikagaku Kogyo Co Ltd 紫外線損傷防御用外用剤
DE19518815A1 (de) * 1995-05-23 1996-11-28 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an alpha-Hydroxyfettsäuren
FR2745179A1 (fr) * 1996-02-28 1997-08-29 Gattefosse Holding Melange maitre actif pour la preparation d'une composition dermocosmetique, composition dermocosmetique contenant ce melange, et methode pour la preparation de ce melange
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EP0807429A1 (en) * 1996-05-13 1997-11-19 Unilever Plc Cosmetic composition with retinol unsaturated fatty acid esters
WO1998050012A1 (en) * 1997-05-02 1998-11-12 Gist-Brocades B.V. Stable vitamin c concentrates
WO1998052532A1 (en) * 1997-05-23 1998-11-26 The Procter & Gamble Company Skin care compositions and method of improving skin appearance
WO1998052533A1 (en) * 1997-05-23 1998-11-26 The Procter & Gamble Company Skin care compositions and method of improving skin appearance
WO1998058628A1 (en) * 1997-06-20 1998-12-30 Mary Kay Inc. Cosmetic composition containing a whitening agent and an exfoliant
FR2767693A1 (fr) * 1997-09-02 1999-03-05 Oreal Emulsion contenant de l'acide ascorbique et ses utilisations dans les domaines cosmetique et dermatologique
US5939082A (en) * 1995-11-06 1999-08-17 The Procter & Gamble Company Methods of regulating skin appearance with vitamin B3 compound
US5968528A (en) * 1997-05-23 1999-10-19 The Procter & Gamble Company Skin care compositions
US5972359A (en) * 1997-05-23 1999-10-26 The Procter & Gamble Company Skin care compositions and method of improving skin appearance
US6013270A (en) * 1998-04-20 2000-01-11 The Procter & Gamble Company Skin care kit
US6024942A (en) * 1996-02-09 2000-02-15 The Procter & Gamble Company Photoprotective compositions
WO2000013659A2 (en) * 1998-09-08 2000-03-16 Indústria e Comércio de Cosméticos Natura Ltda. Process and composition for enhancing the action of vitamin a on the cellular activity of an individual, and use of vitamin c
FR2783713A1 (fr) * 1998-09-29 2000-03-31 Oreal Utilisation d'une gomme de silicone pour stabiliser l'acide ascorbique et nouvelles compositions contenant ces composants
WO2000028961A1 (en) * 1998-11-13 2000-05-25 The Procter & Gamble Company A skin lightening composition containing an ascorbic acid compound
US6174533B1 (en) 1997-05-23 2001-01-16 The Procter & Gamble Company Skin care compositions and method of improving skin appearance
US6183761B1 (en) 1998-03-16 2001-02-06 The Procter & Gamble Company Compositions for regulating skin appearance
US6238678B1 (en) 1995-11-06 2001-05-29 The Procter & Gamble Company Methods of regulating skin appearance with vitamin B3 compound
WO2001070190A2 (en) * 2000-03-23 2001-09-27 Unilever Plc Cosmetic compositions
WO2001074320A2 (de) * 2000-03-31 2001-10-11 Henkel Kommanditgesellschaft Auf Aktien Verwendung von protease-inhibitoren in der kosmetik und pharmazie
USH2013H1 (en) 1997-05-23 2002-02-05 The Procter & Gamble Company Skin care compositions
US6403064B1 (en) 1998-12-22 2002-06-11 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Skin lightening composition
USH2043H1 (en) 1997-05-23 2002-08-06 The Procter & Gamble Company Skin care compositions
US6436416B2 (en) 2000-04-18 2002-08-20 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Cosmetic skin conditioning compositions containing high performing retinyl esters
US6436378B1 (en) * 2001-02-28 2002-08-20 Colgate-Palmolive Company Composition
US6465510B2 (en) 1997-09-02 2002-10-15 L'oreal Emulsion containing ascorbic acid and its uses in the cosmetics and dermatological fields
EP0885000B1 (en) * 1996-03-01 2003-04-16 Johnson & Johnson Consumer Companies, Inc. Topical compositions comprising an oil-in-water emulsion and a retinoid
US6551602B1 (en) 1999-07-30 2003-04-22 Conopco, Inc. Skin care composition containing conjugated linoleic acid and a phenolic compound
EP1264593A3 (en) * 2001-06-08 2003-09-24 Shiseido Company, Ltd. Method of preventing darkening of skin or inhibiting melanization of melanin monomer and polymerization inhibitor of biological dihydroxyindole compound
WO2003082238A1 (de) * 2002-03-28 2003-10-09 Coty B.V. Hautaufhellendes kosmetikum
KR100472104B1 (ko) * 2000-08-04 2005-03-07 네비온 주식회사 미백용 피부외용제 조성물
US6942870B2 (en) 1997-06-04 2005-09-13 The Regents Of The University Of Michigan Compositions and methods using direct MMP inhibitors for inhibiting photoaging of skin
WO2005092283A1 (en) 2004-03-26 2005-10-06 Dsm Ip Assets B.V. Composition comprising an hdac inhibitor in combination with a retinoid
WO2011158864A1 (ja) * 2010-06-15 2011-12-22 国立大学法人 奈良先端科学技術大学院大学 レチノール修飾コラーゲン、その製造方法およびそれを含む皮膚外用組成物
US20140255523A1 (en) * 2010-06-30 2014-09-11 Avon Products, Inc. Use of Tiliacora Triandra in Cosmetics and Compositions Thereof
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JPH07291846A (ja) * 1994-04-26 1995-11-07 Kanebo Ltd 皮膚化粧料
AU1275599A (en) * 1998-10-23 2000-05-15 Procter & Gamble Company, The Skin care compositions
DE19935140A1 (de) * 1999-07-27 2001-02-15 Henkel Kgaa Neue Glykosyltransferase, ihre Herstellung und Verwendung
US6521668B2 (en) 1999-12-14 2003-02-18 Avon Products, Inc. Cosmetic composition and methods of use
KR20010060882A (ko) * 1999-12-28 2001-07-07 서경배 미백용 피부외용제 조성물
JP5113755B2 (ja) * 2005-09-23 2013-01-09 ディーエスエム アイピー アセッツ ビー．ブイ． ヒドロキシ脂肪酸を含む化粧品組成物
FR3040879B1 (fr) * 2015-09-10 2017-10-13 Oreal Composition filtrante anhydre comprenant une phase grasse siliconee

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US5545399A (en) * 1993-10-26 1996-08-13 Chesebrough-Pond's Usa Co. Cosmetic composition
WO1995011662A1 (en) * 1993-10-26 1995-05-04 Unilever Plc Cosmetic composition comprising a hydrocalchone and optionally retinol or a derivative thereof
FR2715844A1 (fr) * 1994-02-04 1995-08-11 Oreal Emulsion contenant de l'acide ascorbique stabilisé, procédé de traitement cosmétique la mettant en Óoeuvre, ses utilisations.
EP0670157A1 (fr) * 1994-02-04 1995-09-06 L'oreal Emulsion contenant de l'acide ascorbique stabilisé
US5552446A (en) * 1994-02-04 1996-09-03 L'oreal Emulsion containing stabilized ascorbic acid, cosmetic treatment process using it and uses thereof
WO1996017589A1 (en) * 1994-12-08 1996-06-13 Kao Corporation Method of smoothing or removing wrinkles and method of stimulating collagen synthesis
JPH08245362A (ja) * 1995-03-08 1996-09-24 Seikagaku Kogyo Co Ltd 紫外線損傷防御用外用剤
DE19518815A1 (de) * 1995-05-23 1996-11-28 Beiersdorf Ag Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an alpha-Hydroxyfettsäuren
US6217888B1 (en) 1995-11-06 2001-04-17 The Procter & Gamble Company Methods of regulating skin appearance with vitamin B3 compound
US6238678B1 (en) 1995-11-06 2001-05-29 The Procter & Gamble Company Methods of regulating skin appearance with vitamin B3 compound
US5939082A (en) * 1995-11-06 1999-08-17 The Procter & Gamble Company Methods of regulating skin appearance with vitamin B3 compound
US6024942A (en) * 1996-02-09 2000-02-15 The Procter & Gamble Company Photoprotective compositions
FR2745179A1 (fr) * 1996-02-28 1997-08-29 Gattefosse Holding Melange maitre actif pour la preparation d'une composition dermocosmetique, composition dermocosmetique contenant ce melange, et methode pour la preparation de ce melange
EP0885000B1 (en) * 1996-03-01 2003-04-16 Johnson & Johnson Consumer Companies, Inc. Topical compositions comprising an oil-in-water emulsion and a retinoid
CN1133417C (zh) * 1996-04-23 2004-01-07 普罗克特和甘保尔公司 维生素b3化合物调节皮肤外观的方法
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WO1997039733A1 (en) * 1996-04-23 1997-10-30 The Procter & Gamble Company Methods of regulating skin appearance with vitamin b3 compound
KR100357848B1 (ko) * 1996-04-23 2002-12-18 더 프록터 앤드 갬블 캄파니 비타민비3화합물을포함하는피부외관을조절하기위한국소용조성물
US5885595A (en) * 1996-05-13 1999-03-23 Elizabeth Arden Co., Division Of Conopco, Inc. Cosmetic composition with a retinol fatty acid ester
EP0807429A1 (en) * 1996-05-13 1997-11-19 Unilever Plc Cosmetic composition with retinol unsaturated fatty acid esters
WO1998050012A1 (en) * 1997-05-02 1998-11-12 Gist-Brocades B.V. Stable vitamin c concentrates
US6183729B1 (en) 1997-05-02 2001-02-06 Cosmoferm B.V. Stable vitamin C concentrates
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US5972359A (en) * 1997-05-23 1999-10-26 The Procter & Gamble Company Skin care compositions and method of improving skin appearance
US5968528A (en) * 1997-05-23 1999-10-19 The Procter & Gamble Company Skin care compositions
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US6174533B1 (en) 1997-05-23 2001-01-16 The Procter & Gamble Company Skin care compositions and method of improving skin appearance
WO1998052532A1 (en) * 1997-05-23 1998-11-26 The Procter & Gamble Company Skin care compositions and method of improving skin appearance
US6942870B2 (en) 1997-06-04 2005-09-13 The Regents Of The University Of Michigan Compositions and methods using direct MMP inhibitors for inhibiting photoaging of skin
WO1998058628A1 (en) * 1997-06-20 1998-12-30 Mary Kay Inc. Cosmetic composition containing a whitening agent and an exfoliant
FR2767693A1 (fr) * 1997-09-02 1999-03-05 Oreal Emulsion contenant de l'acide ascorbique et ses utilisations dans les domaines cosmetique et dermatologique
US6239174B1 (en) 1997-09-02 2001-05-29 L'oreal Emulsion containing ascorbic acid and its uses in the cosmetics and dermatological fields
EP0904775A1 (fr) * 1997-09-02 1999-03-31 L'oreal Emulsion contenant de l'acide ascorbique et ses utilisations dans les domaines cosmétique et dermatologique
US6465510B2 (en) 1997-09-02 2002-10-15 L'oreal Emulsion containing ascorbic acid and its uses in the cosmetics and dermatological fields
US6183761B1 (en) 1998-03-16 2001-02-06 The Procter & Gamble Company Compositions for regulating skin appearance
US6013270A (en) * 1998-04-20 2000-01-11 The Procter & Gamble Company Skin care kit
WO2000013659A2 (en) * 1998-09-08 2000-03-16 Indústria e Comércio de Cosméticos Natura Ltda. Process and composition for enhancing the action of vitamin a on the cellular activity of an individual, and use of vitamin c
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US6967217B1 (en) 1998-09-08 2005-11-22 Natura Cosmetico S.A. Process and composition for enhancing the action of vitamin a on the cellular activity of an individual, and use of vitamin c
US6328983B1 (en) 1998-09-29 2001-12-11 L'oreal Use of a silicone gum to stabilize ascorbic acid, and novel compositions comprising these components
FR2783713A1 (fr) * 1998-09-29 2000-03-31 Oreal Utilisation d'une gomme de silicone pour stabiliser l'acide ascorbique et nouvelles compositions contenant ces composants
EP0998915A1 (fr) * 1998-09-29 2000-05-10 L'oreal Utilisation d'une gomme de silicone pour stabiliser l'acide ascorbique, et nouvelles compositions contenant ces composants
WO2000028961A1 (en) * 1998-11-13 2000-05-25 The Procter & Gamble Company A skin lightening composition containing an ascorbic acid compound
US6403064B1 (en) 1998-12-22 2002-06-11 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Skin lightening composition
US6551602B1 (en) 1999-07-30 2003-04-22 Conopco, Inc. Skin care composition containing conjugated linoleic acid and a phenolic compound
WO2001070190A3 (en) * 2000-03-23 2002-05-10 Unilever Plc Cosmetic compositions
WO2001070190A2 (en) * 2000-03-23 2001-09-27 Unilever Plc Cosmetic compositions
WO2001074320A3 (de) * 2000-03-31 2002-04-11 Henkel Kgaa Verwendung von protease-inhibitoren in der kosmetik und pharmazie
WO2001074320A2 (de) * 2000-03-31 2001-10-11 Henkel Kommanditgesellschaft Auf Aktien Verwendung von protease-inhibitoren in der kosmetik und pharmazie
US6436416B2 (en) 2000-04-18 2002-08-20 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Cosmetic skin conditioning compositions containing high performing retinyl esters
KR100472104B1 (ko) * 2000-08-04 2005-03-07 네비온 주식회사 미백용 피부외용제 조성물
WO2002067886A3 (en) * 2001-02-28 2003-03-20 Colgate Palmolive Co Skin composition
US6436378B1 (en) * 2001-02-28 2002-08-20 Colgate-Palmolive Company Composition
US6861050B2 (en) 2001-06-08 2005-03-01 Shiseido Company, Ltd. Method of preventing darkening of skin or inhibiting melanization of melenin monomer and polymerization inhibitor of biological dihydroxyindole compound
EP1264593A3 (en) * 2001-06-08 2003-09-24 Shiseido Company, Ltd. Method of preventing darkening of skin or inhibiting melanization of melanin monomer and polymerization inhibitor of biological dihydroxyindole compound
WO2003082238A1 (de) * 2002-03-28 2003-10-09 Coty B.V. Hautaufhellendes kosmetikum
WO2005092283A1 (en) 2004-03-26 2005-10-06 Dsm Ip Assets B.V. Composition comprising an hdac inhibitor in combination with a retinoid
WO2011158864A1 (ja) * 2010-06-15 2011-12-22 国立大学法人 奈良先端科学技術大学院大学 レチノール修飾コラーゲン、その製造方法およびそれを含む皮膚外用組成物
US9238688B2 (en) 2010-06-15 2016-01-19 National University Corporation NARA Institute of Science and Technology Retinol-modified collagen, method for producing same, and external composition for skin containing same
US20140255523A1 (en) * 2010-06-30 2014-09-11 Avon Products, Inc. Use of Tiliacora Triandra in Cosmetics and Compositions Thereof
FR3067933A1 (fr) * 2017-06-21 2018-12-28 L'oreal Modulateurs de l’opsine 3 dans la modulation de la pigmentation de la peau
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JPH08502742A (ja) 1996-03-26
AU680844B2 (en) 1997-08-14
EP0666735B1 (en) 1998-10-07
GB9223235D0 (en) 1992-12-16
DE69321479D1 (de) 1998-11-12
ZA938173B (en) 1995-05-02
EP0666735A1 (en) 1995-08-16
ES2123670T3 (es) 1999-01-16
BR9307375A (pt) 1999-08-31
HK1014238A1 (en) 1999-09-24
IN179844B (US07943777-20110517-C00090.png) 1997-12-20
KR950703928A (ko) 1995-11-17
CA2147262A1 (en) 1994-05-11
DE69321479T2 (de) 1999-03-11
AU5420194A (en) 1994-05-24

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