WO2001013877A1 - Procede destine a reduire les irritations cutanees et les brulure provoquees par un acide carboxylique faible - Google Patents
Procede destine a reduire les irritations cutanees et les brulure provoquees par un acide carboxylique faible Download PDFInfo
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- WO2001013877A1 WO2001013877A1 PCT/EP2000/007303 EP0007303W WO0113877A1 WO 2001013877 A1 WO2001013877 A1 WO 2001013877A1 EP 0007303 W EP0007303 W EP 0007303W WO 0113877 A1 WO0113877 A1 WO 0113877A1
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- acid
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- skin
- water
- peg
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- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
-
- 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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/362—Polycarboxylic 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
- A61K8/33—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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated 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
- A61K8/676—Ascorbic acid, i.e. vitamin C
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
Definitions
- This invention relates to a cosmetic method for reducing skin irritation and sting from weak carboxylic acid by polyethylene glycol .
- Cosmetic products which improve the appearance of skin are increasingly popular with consumers. Frequently, consumers seek to alleviate or delay the signs of aged or photo-aged skin, such as fine lines and wrinkles, dry and sagging skin.
- hydroxy acids and several other weak carboxylic acids have been proven to deliver cosmetic benefits, such as improvement in the appearance of photo- -damaged or naturally aged skin, skin lightening, treatment of age spots, etc.
- their use at high concentrations may occasionally be associated with skin irritation, e.g. skin redness and stinging sensation upon application.
- these actives are most often delivered as oil-in-water emulsions.
- the final composition pH should be higher than 3 in order to prevent deleterious effects to skin tissues and unacceptable levels of irritation.
- Water soluble weak acids when delivered from an oil-in-water emulsion at acidic pH often induce high levels of sting. The sting occurs immediately after application, reaches a maximum intensity usually by 5-8 minutes after application and then begins to reduce in intensity.
- the irritation can be ameliorated by lowering the amount of an active ingredient in the composition or by reducing the active's penetration through the skin.
- a serious drawback of both approaches is that the efficacy is impaired.
- the weak acid related irritation can be reduced by raising the composition's pH but this method yields reduced efficacy due to a decreased acid penetration through the skin. It is desirable to reduce or eliminate the irritation potential of weak acids while maintaining their efficacy.
- Polyethylene glycol has been used in cosmetic compositions, which also contain an alpha hydroxy acid. See for instance US Patent 5,863,943 (Groh et al . ) and US Patent 5,411,734 (Vargas et al . ) .
- the prior art described above does not disclose the anti- sting or anti-irritant ability of polyethylene glycol.
- the invention provides a method for reducing skin irritation caused by the topical application of a composition containing a weak carboxylic acid, the method comprising topically applying polyethylene glycol in a cosmetically acceptable vehicle.
- the present invention is based, at least on part, on the discovery that polyethylene glycol reduces the sting and/or irritation that may be caused by weak carboxylic acids, without impairing their delivery to the skin.
- skin as used herein includes the skin on the face, neck, chest, back, arms, armpits, hands and scalp.
- the molecular weight herein is expressed in Dalton (D) .
- Polyethylene glycol (PEG) is a water-soluble, thermoplastic polymer produced by the heterogeneous polymerisation of ethylene oxide.
- the white, free- flowing resins are characterised by the following structural formula: -(-CH 2 CH 2 0-) n .
- the molecular weight of PEGs suitable for use in the present invention generally ranges from 200 D to several (e.g. five) million D, preferably from 200 D to 20 KD, to maintain anti-irritation efficacy, yet to minimise an increase in formulation viscosity.
- the amount of polyethylene glycol in the inventive composition ranges from 0.1 to 20%, preferably from 1 to 15%, most preferably from 0.5 to 10%.
- a weak carboxylic acid suitable for use in the inventive compositions is an acid with a dissociation constant, pKa, of above about 2.
- pKa a dissociation constant
- the pKa is above about 3, most preferably in the range of from about 3 to about 5.
- lactic acid-lactate ion is an example of a conjugate acid-base pair.
- Acids so defined can only manifest their properties by reacting with bases.
- acids react with water, the latter acting as a base:
- pK a is the negative logarithm of K a , and is equal to the pH at which the concentrations of HA and A " are equal.
- the pK a for alpha hydroxy acids is generally from 2-4, for monocarboxylic acids from 3-5, for alpha amino acids from 2-3; and for salicylic acid it is 3.0.
- the pK a of a weak water-soluble acid is obtained by titrating it with a strong base such as sodium hydroxide (NaOH) .
- a strong base such as sodium hydroxide (NaOH)
- a procedure for determining pKa for a known weak acid is as follows: The following materials are needed: a sample of pure acid for which pKa is to be determined; C0 2 -free deionized distilled water (prepared by boiling deionized distilled water for 5 minutes); Commercial 0. IN NaOH volumetric standard, certified to 0.1005-0.0995 N, eg. Fisher Scientific SS276; 100-ml calibrated glass burette; 125-ml Erlenmeyer flask pH meter, e.g. Corning Model 140 with standard combination electrode for pH; pH buffers, pH 4.00, 7.00, and 10.00, certified to ⁇ 0.01 pH unit at 25, e.g. Fisher Scientific SB101, SB107, and SB115 magnetic stirrer.
- the pH electrode is inserted into the acid solution and positioned and secured so that it does not interfere with the stirring bar.
- the initial pH is recorded.
- gentle stirring is begun such that the pH reading is not affected.
- the burette is positioned over the flask to allow incremental addition of the 0.1 N standard NaOH to the 0.1 N acid solution.
- the initial pH is verified and incremental addition of the base begun.
- the volumes of base added and the resulting pH readings are recorded.
- the aim is to record pH changes of 0.2 to 0.3 units or volume increases of about 5ml, whichever comes first. Incremental additions are continued until at least 60 ml of the base have been added and the steep change in pH levels off .
- the data is plotted with the volume of base as the x- axis and pH as the y-axis. The points observed are plotted and a smooth line drawn through them.
- the volume of base added to obtain the equivalence point is determined, i.e. the volume at which one normal- equivalent of base has been added and the acid has been completely neutralised.
- the equivalence point volume corresponds to the volume of base at the vertical portion of the curve. If the steep portion of the curve is not vertical, the equivalence point can be obtained by locating the volumes of the base at the two end points that bracket the steep change in pH. The mean of the two volumes is the equivalence point.
- the midpoint of the titration is the point at which 0.5 normal -equivalents of base have been added, and the acid has been one-half (50%) neutralised.
- the pH corresponding to the midpoint of the titration is the pK a of the acid. This is the pH at which 50% of the acid has been neutralised, that is, the molecule exists 50% in the non-ionised form and 50% as the anion.
- suitable weak carboxylic acids include but are not limited to: alpha- or beta-hydroxyacids, dicarboxylic acids, tricarboxylic acids, ascorbic acid, oxamic acid and mixtures thereof.
- Preferred carboxylic acids, due to their anti-ageing efficacy, are:
- the amount of weak acid in the inventive composition ranges from 0.01 to 20, preferably from 1 to 15 and most preferably from 2 to 12, by weight of the composition.
- the acid may be present as a salt, e.g. an ammonium, potassium or sodium salt.
- compositions employed in the inventive method may have any pH in the general range of 2.5 to 10, the inventive methods are particularly useful in compositions having an acidic pH, preferably 3-6 and most preferably at a pH of 3-5, because such compositions, although efficacious, are particularly irritating.
- compositions employed in the invention comprise a cosmetically acceptable vehicle to act as a diluant, dispersant or carrier for weak carboxylic acid and PEG, so as to facilitate their distribution when the composition is applied to the skin.
- the vehicle may be aqueous or an emulsion. Water when present will be in amounts which may range from 5 to 99%, preferably from 40 to 90%, optimally from 50 and 85% by weight .
- the vehicle is preferably at least 50 wt . % water by weight of the vehicle.
- the compositions are preferably oil -water emulsions, in order to improve dermal delivery of hydroxy acids (See Sah et al . in J. Cosmet . Sci . 49 , 257 -273 , 1998) . Such improved delivery is frequently accompanied by increased irritation/sting, making the use of PEG in such emulsions particularly critical.
- water comprises at least 50 wt . % of the inventive emulsion, most preferably from 50 to 85 wt.%, by weight of the composition.
- relatively volatile solvents may also serve as carriers within compositions employed in the present invention.
- monohydric C_-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 if present may range anywhere from 0.1 to 50%, preferably between 1 and 20% by weight.
- Silicone oils may be divided into the volatile and non-volatile variety.
- volatile refers to those materials which have a measurable vapour 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.
- Nonvolatile silicone oils useful as an emollient material include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers .
- the essentially nonvolatile 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.
- Suitable emollients are:
- Alkenyl or alkyl esters of fatty acids having fromlO 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 monostearate, 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.
- Wax esters such as beeswax, spermaceti, myristyl myristate, stearyl stearate and arachidyl behenate.
- Sterols esters of which cholesterol fatty acid esters are examples thereof.
- 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.
- Thickeners may also be utilised 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, 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
- Surfactants may also be present in cosmetic compositions of the present invention. Total concentration of the surfactant will range from 0.1 to 40%, preferably from 1 to 20%, optimally from 1 to 5% by weight of the composition.
- the surfactant may be selected from the group consisting of anionic, nonionic, cationic and amphoteric surfactants.
- nonionic surfactants are those with a C 10 -C 20 fatty alcohol or acid hydrophobe condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe; C 2 -C 10 alkyl phenols condensed with from 2 to 20 moles of alkylene oxide; mono- and di- fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan, mono- and di- C 8 -C 20 fatty acids; block copolymers (ethylene oxide/propylene oxide) ; 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 sulfate and sulfonates, alkyl sulfates and sulfonates, alkylbenzene sulfonates, alkyl and dialkyl sulfosuccinates, C 8 -C 20 acyl isethionates , acyl glutamates, C 8 -C 20 alkyl ether phosphates and combinations thereof .
- Actives are defined as skin benefit agents other than emollients and other than ingredients that merely improve the physical characteristics of the composition. Although not limited to this category, general examples include additional anti-sebum ingredients and sunscreens.
- Sunscreens include those materials commonly employed to block ultraviolet light.
- Illustrative compounds are the derivatives of PABA, cinnamate and salicylate.
- avobenzophenone Parsol 1789 ®
- octyl methoxycinnamate and 2-hydroxy-4-methoxy benzophenone also known as oxybenzone
- 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 p-hydroxybenzoic 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.
- composition employed in the invention is intended primarily as a product for topical application to human skin, especially as an agent to improve the appearance of aged or photoaged 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.
- 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.
- This example measured sting caused by formulations containing glycolic acid.
- Procedure for in-vivo sting test This was a randomized, double blind study where each subject evaluated one test formulation and a control formulation or two test formulations on contralateral nasolabial folds. During the qualification phase, each subject evaluated an 8% glycolic acid test versus a vehicle control (0% glycolic) . Subjects with established left/right balanced sensitivity to glycolic acid were qualified. A maximum of 20 qualified subjects (minimum of 15) were utilized in each subsequent test. One paired comparison was made on each testing day, with a minimum of 3 days between sting testing throughout the study. Subjects underwent a 15 second Ivory soap wash regime immediately prior to product testing for enhancing sting response. Any subjects experiencing any stinging/burning on the test sites immediately prior to product application did not have products applied.
- Study personnel then applied one test formulation and one control or test formulation simultaneously to the appropriate left/right test site, and gently but thoroughly rubbed in. Subjects compared the stinging potential of the two formulations, over a 7.5 minute period using a self-assessment questionnaire.
- Sting/Burn Propensity The degree of stinging/burning felt on the left and right inner cheek and crease of the nose was evaluated using the following scale at the times indicated in the Tables below:
- 0 -no stinging / burning 1 -very slight stinging / burning; 2 -slight stinging / burning; 3 - moderate stinging / burning; 4 -moderately high stinging / burning; 5 -high stinging / burning; 6 -extreme stinging / burning.
- This example measured the effect of PEG 200D on glycolic acid sting at pH 3.8 in Base Formula A.
- the in-vivo sting test and Base Formula A are described in Example 1.
- Base Formula A was prepared without the glycolic acid, base, and PEG.
- the PEG was solubilised in a separate beaker containing glycolic acid + base (ammonium hydroxide) and a small level of water from the formulation (no more than 5% is needed)- thus, the original Base Formula A was originally made with 5% less water.
- the glycolic acid/PEG solution was then post added to the Base Formula A during the cool down stage (usually at a temperature of about 45°C) .
- the results obtained are summarised in Tables 2A and 2B.
- the emulsion concentrate was made using all ingredients except glycolic / base / PEG and without all the water. In a separate beaker glycolic + base + PEG + about 5% of the total water was combined and mixed until the PEG solubilises completely. This mixture was then post added to the emulsion. The pH was then adjusted to the correct pH using base, and then the remainder of the water was added to qs . 100%.
- Example 1 tested the various compounds for their ability to reduce sting.
- the test procedure and Base Formula A are described in Example 1.
- the results obtained are summarised in Tables 6A and 6B .
- This example tested the effect of polyethylene glycol on the delivery of glycolic acid molecules to the skin layers.
- transepidermal water loss was determined using a ServoMed EP1 evaporimeter . Skin discs allowing water losses of >5 g/m2 per hr were replaced. The skin discs were dosed with 2 ⁇ L of product containing the nonlabelled active plus an insignificant weight of the active radiolabelled with 3H or 14C at about 30 microCurie/gram product. The dose was delivered via a displaced volume pipette and spread on the 9-mm diameter exposed skin surface with either a latex finger cot stretched over a cotton tip applicator. Contact times were 6 hours, with receptor fluid being sampled at either 1- or 2-hour intervals in scintillation vials.
- the skin surface was rinsed with three ⁇ l- ml aliquots of water, the skin discs were removed from the apparatus, and blotted with 1/3 of tissue paper (Kim Wipe) .
- the upper surface was tape-stripped 9 times with Scotch transparent tape to obtain the stratum corneum, and the epidermis was separated from the dermis with a scalpel.
- Examples 1 - 5 demonstrate that polyethylene glycol reduced the sting caused by weak acids.
- Other known anti-irritants such as hydrocortisone, as well as a polysaccharide, arabinogalactan, did not reduce the sting caused by weak carboxylic acids (Comparative Example 6) .
- the addition of PEG did not adversely affect the delivery of actives to skin layers (Example 7) .
- Example 8 illustrates topical compositions according to the present invention.
- the compositions can be processed in a conventional manner and are suitable for cosmetic use.
- the compositions are suitable for application to aged and/or UV-damaged skin to improve the appearance and the feel thereof as well as for application to healthy skin to prevent or retard deterioration thereof.
- a typical oil-in-water emulsion within the scope of the invention is as follows:
- a typical water- in-oil dispersion within the scope of the invention is as follows:
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Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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AU69881/00A AU6988100A (en) | 1999-08-20 | 2000-07-31 | A method for reducing skin irritation and sting from weak carboxylic acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US15011299P | 1999-08-20 | 1999-08-20 | |
US60/150,112 | 1999-08-20 |
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WO2001013877A1 true WO2001013877A1 (fr) | 2001-03-01 |
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PCT/EP2000/007303 WO2001013877A1 (fr) | 1999-08-20 | 2000-07-31 | Procede destine a reduire les irritations cutanees et les brulure provoquees par un acide carboxylique faible |
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WO (1) | WO2001013877A1 (fr) |
Cited By (13)
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GB1173467A (en) * | 1966-04-12 | 1969-12-10 | United Aircraft Corp | Gas Discharge Structures for Gas Turbine Engines |
FR2841135A1 (fr) * | 2002-06-25 | 2003-12-26 | Oreal | Procede non therapeutique de diagnotisc de la peau sensible |
EP1374913A1 (fr) * | 2002-06-25 | 2004-01-02 | L'oreal | Procédés non thérapeutiques d'évaluation de la neuro-sensibilité cutanée, kit et utilisation d'un kit |
WO2008074634A1 (fr) * | 2006-12-18 | 2008-06-26 | Aco Hud Nordic Ab | Formulations topiques présentant un pouvoir d'irritation réduit |
EP1941859A1 (fr) * | 2006-12-18 | 2008-07-09 | ACO Hud Nordic AB | Formulations pour application topique |
US8100830B2 (en) | 2002-06-25 | 2012-01-24 | Societe L'oreal S.A. | Non-therapeutic methods of evaluating skin neurosensitivity, kit and use of a kit for implementing the method |
WO2015000478A1 (fr) * | 2013-07-02 | 2015-01-08 | Henkel Ag & Co. Kgaa | Composition nettoyante à haute teneur en acides gras |
US9211275B2 (en) | 2008-01-04 | 2015-12-15 | Isis Innovation Ltd. | Ketone bodies and ketone body esters as blood lipid lowering agents |
US9579302B2 (en) | 2012-11-05 | 2017-02-28 | Tdeltas | Ketone bodies to protect tissues from damage by ionizing radiation |
US10051880B2 (en) | 2008-08-21 | 2018-08-21 | Oxford University Innovation Limited | Hydroxybutyrate ester and medical use thereof |
US10660958B2 (en) | 2010-02-22 | 2020-05-26 | Tdeltas Limited | Nutritional composition |
US10821062B2 (en) | 2013-03-12 | 2020-11-03 | Tdeltas Limited | Compound for use in protecting skin |
US11230722B2 (en) | 2003-06-03 | 2022-01-25 | Oxford University Innovation Limited | Nutritional supplements and therapeutic compositions comprising (r)-3-hydroxybutyrate derivatives |
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-
2000
- 2000-07-31 AU AU69881/00A patent/AU6988100A/en not_active Abandoned
- 2000-07-31 WO PCT/EP2000/007303 patent/WO2001013877A1/fr active Application Filing
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JPS5535025A (en) * | 1978-09-05 | 1980-03-11 | Akira Oota | Liquid remedy for dermatophytosis and its preparation |
US5320838A (en) * | 1992-12-21 | 1994-06-14 | Pro Cure Products, Ltd. | Protectant for irritated skin containing polyethyleneglycols, polyvinylether salt anhydride and polyvinylpyrrolidone |
US5935584A (en) * | 1994-01-13 | 1999-08-10 | Elizabeth Arden Company | Vitamin C delivery system |
EP0729745A1 (fr) * | 1995-02-28 | 1996-09-04 | Unilever Plc | Système de délivrance de vitamine C |
US5879688A (en) * | 1995-03-09 | 1999-03-09 | Focal, Inc. | Hydroxy-acid cosmetics |
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US5736567A (en) * | 1995-07-25 | 1998-04-07 | L'oreal | Stable composition containing ascorbic acid |
US5885593A (en) * | 1995-09-28 | 1999-03-23 | The Andrew Jergens Company | Skin care composition including cyclodextrin materials and method for treating skin therewith |
WO1999038488A2 (fr) * | 1998-01-29 | 1999-08-05 | Unilever Plc | Pains dermatologiques |
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Cited By (21)
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GB1173467A (en) * | 1966-04-12 | 1969-12-10 | United Aircraft Corp | Gas Discharge Structures for Gas Turbine Engines |
FR2841135A1 (fr) * | 2002-06-25 | 2003-12-26 | Oreal | Procede non therapeutique de diagnotisc de la peau sensible |
EP1374913A1 (fr) * | 2002-06-25 | 2004-01-02 | L'oreal | Procédés non thérapeutiques d'évaluation de la neuro-sensibilité cutanée, kit et utilisation d'un kit |
US8100830B2 (en) | 2002-06-25 | 2012-01-24 | Societe L'oreal S.A. | Non-therapeutic methods of evaluating skin neurosensitivity, kit and use of a kit for implementing the method |
US11230722B2 (en) | 2003-06-03 | 2022-01-25 | Oxford University Innovation Limited | Nutritional supplements and therapeutic compositions comprising (r)-3-hydroxybutyrate derivatives |
WO2008074634A1 (fr) * | 2006-12-18 | 2008-06-26 | Aco Hud Nordic Ab | Formulations topiques présentant un pouvoir d'irritation réduit |
EP1941859A1 (fr) * | 2006-12-18 | 2008-07-09 | ACO Hud Nordic AB | Formulations pour application topique |
EP1941860A1 (fr) * | 2006-12-18 | 2008-07-09 | ACO Hud Nordic AB | Formulations pour application topique |
US10154982B2 (en) | 2008-01-04 | 2018-12-18 | Oxford University Innovation Limited | Ketone bodies and ketone body esters as blood lipid lowering agents |
US11311509B2 (en) | 2008-01-04 | 2022-04-26 | Oxford University Innovation Limited | Ketone bodies and ketone body esters as blood lipid lowering agents |
US9211275B2 (en) | 2008-01-04 | 2015-12-15 | Isis Innovation Ltd. | Ketone bodies and ketone body esters as blood lipid lowering agents |
US10051880B2 (en) | 2008-08-21 | 2018-08-21 | Oxford University Innovation Limited | Hydroxybutyrate ester and medical use thereof |
US10660958B2 (en) | 2010-02-22 | 2020-05-26 | Tdeltas Limited | Nutritional composition |
US11571479B2 (en) | 2010-02-22 | 2023-02-07 | Tdeltas | Nutritional composition |
US10478415B2 (en) | 2012-11-05 | 2019-11-19 | Tdeltas Limited | Ketone bodies to protect tissues from damage by ionizing radiation |
US9579302B2 (en) | 2012-11-05 | 2017-02-28 | Tdeltas | Ketone bodies to protect tissues from damage by ionizing radiation |
US11234953B2 (en) | 2012-11-05 | 2022-02-01 | Tdeltas Limited | Ketone bodies to protect tissues from damage by ionizing radiation |
US10821062B2 (en) | 2013-03-12 | 2020-11-03 | Tdeltas Limited | Compound for use in protecting skin |
US10639246B2 (en) | 2013-07-02 | 2020-05-05 | Henkel Ag & Co. Kgaa | Cleansing composition with high fatty acid content |
US20160101027A1 (en) * | 2013-07-02 | 2016-04-14 | Henkel Ag & Co. Kgaa | Cleansing composition with high fatty acid content |
WO2015000478A1 (fr) * | 2013-07-02 | 2015-01-08 | Henkel Ag & Co. Kgaa | Composition nettoyante à haute teneur en acides gras |
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