WO2014004171A2 - Sunscreen compositions containing an ultraviolet radiation-absorbing polyester - Google Patents
Sunscreen compositions containing an ultraviolet radiation-absorbing polyester Download PDFInfo
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- WO2014004171A2 WO2014004171A2 PCT/US2013/046326 US2013046326W WO2014004171A2 WO 2014004171 A2 WO2014004171 A2 WO 2014004171A2 US 2013046326 W US2013046326 W US 2013046326W WO 2014004171 A2 WO2014004171 A2 WO 2014004171A2
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- composition
- absorbing
- oil
- polyester
- water emulsifier
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Classifications
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- 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
- A61K8/85—Polyesters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water 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
- A61K8/55—Phosphorus compounds
-
- 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
Definitions
- UV-absorbing refers to a material or compound, e.g. a polymeric or non-polymeric sunscreen agent or a chemical moiety, which absorbs radiation in some portion of the ultraviolet spectrum (290nm-400nm), such as one having an extinction coefficient of at least about 1000 mol "1 cm "1 , for at least one wavelength within the above- defined ultraviolet spectrum. SPF values disclosed and claimed herein are determined using the in-vitro method described herein below.
- the UV-absorbing polyester is complex.
- a suitable liquid chromatography system is an Agilent 1100/1200 Series high performance liquid chromatography system, the hardware of the which includes 5 modules; a G1379A degasser, a Model G1310A isocratic pump, a 1110 automatic liquid sampler Model G 1313 A, a Model G 1316A thermostatted column compartment, and a Model G1362A refractive index detector (RID).
- the system is controlled using Agilent LC Chemstation software, Revision B.03.02.
- the system is fitted with two Varian MesoPore GPC Columns, 300 x 7.5 mm, 3um, multipore.
- the UV-absorbing polyesters suitable for use in compositions of the present invention may be synthesized by various means known to those skilled in the art, e.g., ring opening of a lactone (cyclic ester) that bears a UV-absorbing moiety; a condensation reaction of a UV- absorbing monomer having both acid and alcohol functionality (e.g., an "A-B" condensation reaction); condensing a polyol functional monomer and a polyacid functional monomer, one or both of which includes UV-absorbing moieties; and the like.
- the mole ratio of monomers may be selected such that the ratio of various monomer pairs is from about 0.25: 1 to about 4: 1.
- the mole fraction of UV-absorbing monomer e.g., UV-absorbing triazole, relative to the total number of moles of all monomers used in the reaction (including the UV-absorbing monomer) is selected to be about 0.39 to about 0.60, or about 0.37 to about 0.42. According to another embodiment, this mole fraction is selected to be about 0.45 or less.
- One particularly suitable UV-absorbing polyester is formed by a transesterification reaction of the following monomers: (1) dimerdiol, C 36 H72O, CAS No. 147853-32-5, which is a C 36 diol; (2) di-trimethylolpropane, C12H2 6 O5, CAS No. 23235-61-2, which is a
- the sunscreen agent consists of, or consists essentially of, the UV-absorbing polyester, as defined herein.
- the sunscreen agent may include additional UV-absorbing polymers, other than those UV-absorbing polyesters, as defined herein, and/or non-UV-absorbing, light- scattering particles.
- Additional UV-absorbing polymers are molecules that can be represented as having one or more structural units that repeat periodically, e.g., at least twice, to generate the molecule, and may be UV-absorbing polyesters, other than those as defined and claimed in this specification.
- Additional UV-absorbing polymers may have a molecular weight of greater than about 1500.
- suitable additional UV-absorbing polymers include benzylidene malonate silicone, including those described in US Patent 6, 193,959, to Bernasconi et al.,.
- a particularly suitable benzylidene malonate includes "Parsol SLX," commercially available from DSM (Royal DSM N.V.) of Heerlen, Netherlands.
- Other suitable additional UV- absorbing polymers are disclosed in US 6, 962,692; US 6,899, 866; and/or US 6,800,274; including hexanedioic acid, polymer with 2,2-dimethyl- l,3-propanediol,
- Non-UV-absorbing, light-scattering particles do not absorb in the UV spectrum, but may enhance SPF by scattering of the incident UV radiation.
- Examples of non-UV- absorbing, light-scattering particles include solid particles having a dimension, e.g., average diameter, from about 0.1 micron to about 10 microns.
- the non-UV- absorbing, light-scattering particle is a hollow particle comprising, or consisting essentially of, an organic polymer or a glass. Suitable organic polymers include acrylic polymers, including acrylic/styrene copolymers, such as those known as SU SPHERES, which are commercially available from Dow Chemical of Midland, Michigan.
- a composition suitable for topical/cosmetic use for application to the human body e.g., keratinaceous surfaces such as the skin, hair, lips, or nails, and especially the skin
- the composition includes one or more UV-absorbing polyesters described herein.
- the concentration of the UV-absorbing polyester is sufficient to provide an SPF of about 10 or greater, particularly in the absence or substantial absence of other UV-absorbing polymers or non-polymeric UV-absorbing sunscreen agents as described herein. Accordingly, the concentration of the UV-absorbing polyester may vary from about 5% to about 50%, such as from about 7% to about 40%, such as from about 10% to about 25% of the composition.
- the concentration of UV-absorbing polyester is about 10% or more, such as about 15% or more, such about 25% or more of the composition. According to certain embodiments where the sunscreen agent consists essentially of the UV-absorbing polyester, the concentration of the UV-absorbing polyester may be about 15% or more.
- compositions of the present invention may have an SPF of about 20 or greater.
- non-polymeric UV-absorbing sunscreen agents that the composition is substantially free of typically may be characterized as "organic” (include predominantly or only atoms selected from carbon, hydrogen, oxygen, and nitrogen) and having no definable repeat unit and typically having molecular weights that are about 600 daltons or less, such as about 500 daltons or less, such as less than 400 daltons.
- aminobenzoic acid and octyldimethyl para-amino benzoic acid octocrylene and other ⁇ , ⁇ - diphenylacrylates; dioctyl butamido triazone; octyl triazone; butyl methoxydibenzoyl methane; drometrizole trisiloxane; and menthyl anthranilate.
- Non-polymeric UV-absorbing sunscreen agents that the composition is substantially free of may include ultraviolet-absorbing particles, such as certain inorganic oxides, including titanium dioxide, zinc oxide, and certain other transition metal oxides.
- ultraviolet screening particles are typically solid particles having a diameter from about 0.1 micron to about 10 microns.
- compositions of the present invention may be used for a variety of cosmetic uses, especially for protection of the skin from UV radiation.
- the compositions thus, may be made into a wide variety of delivery forms. These forms include, but are not limited to, suspensions, dispersions, solutions, or coatings on water soluble or water-insoluble substrates (e.g., substrates such as organic or inorganic powders, fibers, or films).
- Suitable product forms include lotions, creams, gels, sticks, sprays, ointments, mousses, and
- compositions/powders may be employed for various end-uses, such as recreation or daily-use sunscreens, moisturizers, cosmetics/make-up, cleansers/toners, anti- aging products, or combinations thereof.
- compositions of the present invention may be prepared using methodology that is well known by an artisan of ordinary skill in the field of cosmetics formulation.
- compositions of the present invention include a continuous water phase in which a discontinuous oil phase that includes the UV-absorbing polyester is substantially homogeneously distributed.
- the UV-absorbing polyester is dissolved, as opposed to being dispersed or suspended, within the oil phase.
- the oil phase may, in turn, be stabilized within the water phase.
- the oil phase may be such that it is present in discrete droplets or units having an average diameter of about one micron to about 1000 microns, such as from about 1 micron to about 100 microns.
- the percentage of water included in the compositions may range from about 20% to about 90%, such as from about 20% to about 80%, such as from about 30% to about 70%, such as from about 51% to about 80%, such as from about 51% to about 70%, such as from about 51% to about 60%.
- the one or more UV-absorbing polymers in the composition may be combined with a
- composition may further include any of various functional ingredients known in the field of cosmetic chemistry, for example, emollients (including oils and waxes) as well as other ingredients commonly used in personal care compositions, such as humectants, thickeners, opacifiers, fragrances, dyes, solvents for the UV-absorbing polyester, among other functional ingredients.
- emollients including oils and waxes
- solvents for the UV-absorbing polyester include dicaprylyl carbonate available as CETIOL CC from Cognis Corporation of Ambler, Pennsylvania.
- the composition is substantially free of volatile solvents, and, in particular, C1-C4 alcohols such as ethanol and isopropanol.
- composition may be essentially free of ingredients that would render the composition unsuitable for topical use.
- composition may be essentially free of solvents such as volatile solvents, and, in particular, free of volatile organic solvents such as ketones, xylene, toluene, and the like.
- compositions of the present invention include an O/W emulsifier component that includes one or more O/W emulsifiers.
- O/W emulsifier it is meant any of a variety of molecules that are suitable for emulsifying discrete oil-phase droplets in a continuous water phase.
- low molecular weight emulsifiers emulsifiers having a molecular weight of about 2000 daltons or less, such as about 1000 daltons or less.
- the O/W emulsifier may be capable of lowering the surface tension of pure deionized water to 45 dynes per centimeter when added to pure deionized water at a concentration of O/W emulsifier of 0.5% or less at room temperature.
- O/W emulsifiers are sometimes characterized as having a hydrophile-lipophile balance (HLB) that is about 8 or more, such as about 10 or more.
- HLB hydrophile-lipophile balance
- anionic emulsifiers examples include alkyl, aryl or alkylaryl, or acyl-modified versions of the following moieties: sulfates, ether sulfates, monoglyceryl ether sulfates, sulfonates, sulfosuccinates, ether sulfosuccinates, sulfosuccinamates,
- Notable anionic emulsifiers are phosphate esters, such as cetyl phosphate salts, such as potassium cetyl phosphate.
- the concentration of the one or more anionic emulsifiers is from about 0.3% to about 3%, such as from about 1% to about 3%, such as from about 0.5% to about 2.5%, of the weight of the composition.
- the O/W emulsifier component consists essentially of the one or more anionic emulsifiers.
- the O/W emulsifier component is essentially free of non-ionic emulsifiers having an alcohol-functional group with a hydrocarbon chain length of 14-22 carbon atoms.
- Chemical classes of non-ionic emulsifiers having an alcohol functional group may include fatty alcohols, such as various saturated or unsaturated, linear or branched, C7-C22 unethoxylated, aliphatic alcohols, such as those having a single -OH group.
- the fatty alcohol may be derived from plant or animal oils and fats having at least one pendant hydrocarbon-comprising chain.
- the fatty alcohol may have from 14 to about 22 carbon atoms, such as from about 16 to about 18 carbon atoms. Examples of unbranched fatty alcohols include cetyl alcohol and stearyl alcohol.
- the O/W emulsifier component is essentially free of cationic emulsifiers, such as alkyl quaternaries, benzyl quaternaries, ester
- the O/W emulsifier component includes an additional emulsifier such as a non-ionic emulsifier that is devoid of alcohol functional groups, an amphoteric emulsifier, and/or a polymeric emulsifier.
- an additional emulsifier such as a non-ionic emulsifier that is devoid of alcohol functional groups, an amphoteric emulsifier, and/or a polymeric emulsifier.
- amphoteric emulsifiers examples include alkyl betaines, amidoalkyl betaines, alkylamphoacetates; amidoalkyl sultaines; amphophosphates; phosphorylated imidazolines; carboxyalkyl alkyl polyamines; alkylimino-dipropionates; alkylamphoglycinates (mono or di); alkylamphoproprionates; N-alkyl ⁇ -aminoproprionic acids; and alkylpolyamino carboxylates.
- polymeric emulsifier examples include copolymers based on acrylamidoalkyl sulfonic acid such as Aristoflex® AVC and Aristoflex® HMB by Clariant Corporation; and Granthix APP by Grant Industries, Inc.
- compositions of the present invention include a film forming polymer.
- film-forming polymer it is meant a polymer that when dissolved, emulsified, or dispersed in one or more diluents, permits a continuous or semi- continuous film to be formed when it is spread with a liquid vehicle onto smooth glass, and the liquid vehicle is allowed to evaporate.
- the polymer should dry on the glass in a manner in which over the area which it is spread should be predominantly continuous, rather than forming a plurality of discrete, island-like structures.
- the films formed by applying compositions on the skin according to embodiments of the invention described herein are less than, on average, about 100 microns in thickness, such as less than about 50 microns.
- film-forming polymers In contrast to polymeric UV-absorbing polymers, film-forming polymers generally do not absorb ultraviolet radiation and therefore do not meet the requirements for UV-absorbing polymers. Film- forming polymers may be useful in compositions of the present invention in that they may enhance the UV-protection (UV-A, UV-B or both) of the composition and/or enhance the waterproofing or water resistance of the composition.
- Suitable film-forming polymers include natural polymers such as polysaccharides or proteins and synthetic polymers such as polyesters, polyacrylics, polyurethanes, vinyl polymers, polysulfonates, polyureas, polyoxazolines, and the like.
- film-forming polymers include, for example, hydrogenated dimer dilinoleyl/dimethylcarbonate copolymer, available from Cognis Corporation of Ambler, Pennsylvania as COSMEDIA DC; copolymer of vinylpyrrolidone and a long-chain a-olefin, such as those commercially available from ISP Specialty Chemicals of Wayne, New Jersey as GANEX V220; vinylpyrrolidone/tricontanyl copolymers available as GANEX WP660 also from ISP; water-dispersible polyesters, including sulfopolyesters such those commercially available from Eastman Chemical as EASTMAN AQ 38S.
- the amount of film-forming polymer present in the composition may be from about 0.1% to about 5%, or from about 0.1% to about 3%, or from about 0.1% to about 2%.
- the composition includes an emollient used for the prevention or relief of dryness and for the protection of the skin, as well as solubilizing the UV-absorbing polyester.
- Suitable emollients include mineral oils, petrolatum, vegetable oils (e.g. triglycerides such as caprylic/capric triglyceride), waxes and other mixtures of fatty esters, including but not limited to esters of glycerol (e.g, isopropyl palmitate, isopropyl myristate), and silicone oils such as dimethicone.
- mixtures of triglycerides (e.g. caprylic/capric triclycerides) and esters of glycols (e.g. isopropyl myristate) may be used to solubilize the UV-absorbing polyesters.
- the composition includes a pigment suitable for providing color or hiding power.
- the pigment may be one suitable for use in a color cosmetic product, including compositions for application to the hair, nails and/or skin, especially the face,
- Color cosmetic compositions include, but are not limited to, foundations, concealers, primers, blush, mascara, eyeshadow, eyeliner, lipstick, nail polish and tinted moisturizers.
- the pigment suitable for providing color or hiding power may be composed of iron oxides, including red and yellow iron oxides, titanium dioxide, ultramarine and chromium or chromium hydroxide colors, and mixtures thereof.
- the pigment may be a lake pigment, e.g., an organic dye such as azo, indigoid, triphenylmethane, anthraquinone, and xanthine dyes that are designated as D&C and FD&C blues, browns, greens, oranges, reds, yellows, etc., precipitated onto inert binders such as insoluble salts.
- lake pigments include Red #6, Red #7, Yellow #5 and Blue #1.
- the pigment may be an interference pigment.
- interference pigments include those containing mica substrates, bismuth oxycloride substrates, and silica substrates, for instance mica/bismuth oxychloride/iron oxide pigments commercially available as CHROMALITE pigments (BASF), titanium dioxide and/or iron oxides coated onto mica such as commercially available FLAMENCO pigments (BASF), mica/titanium dioxide/iron oxide pigments including commercially available KTZ pigments (Kobo products), CELLINI pearl pigments (BASF), and borosilicate-containing pigments such as REFLECKS pigments (BASF).
- BASF commercially available FLAMENCO pigments
- mica/titanium dioxide/iron oxide pigments including commercially available KTZ pigments (Kobo products), CELLINI pearl pigments (BASF), and borosilicate-containing pigments such as REFLECKS pigments (BASF).
- compositions of the present invention may further comprise one or more other cosmetically active agent(s).
- a "cosmetically active agent” is a compound that has a cosmetic or therapeutic effect on the skin, e.g., agents to treat wrinkles, acne, or to lighten the skin.
- the cosmetically active agent will typically be present in the composition of the invention in an amount of from about 0.001% to about 20% by weight of the composition, e.g., about 0.01% to about 10% such as about 0.1% to about 5% by weight of the composition.
- the composition has a pH that is from about 4.0 to about 8.0, such as from about 5.5 to about 7.0.
- compositions of the present invention have low irritation tendencies. Irritation may be measured using, for example, the MODIFIED TEP TEST as set forth below. A lower
- MODIFIED TEP value of a composition tends to indicate less irritation associated therewith, as compared to a composition having a higher MODIFIED TEP value, which composition tends to cause higher levels of irritation.
- compositions of the present invention have surprisingly low MODIFIED TEP values/lower irritation associated therewith.
- the compositions have a MODIFIED TEP value, as determined according to the MODIFIED TEP TEST as set forth below, of about 0.45 or less.
- the compositions exhibit a MODIFIED TEP value of about 0.40 or less, such as about 0.35 or less, such as about 0.30 or less.
- the compositions of the present invention may be prepared using mixing and blending methodology that is well known by an artisan of ordinary skill.
- a method of making a composition of the present invention includes preparing an oil phase by mixing at least the UV-absorbing polyester with optional oil- soluble or oil-miscible ingredients; and preparing a water phase, by mixing water and optional water-soluble or water-miscible ingredients.
- the oil phase and the water phase may then be mixed in a manner sufficient to substantially homogeneously disperse the oil phase in the water phase such that the water phase is continuous and the oil phase discontinuous.
- compositions of the present invention can be used by topically administering to a mammal, e.g., by the direct laying on, wiping or spreading of the composition on the skin or hair of a human.
- MODIFIED TEP TEST is used in the instant methods and in the following Examples.
- the MODIFIED TEP TEST is used to determine when a composition has reduced irritation according to the present invention.
- the MODIFIED TEP TEST is designed to evaluate the ability of a test material to disrupt the permeability barrier formed by a confluent monolayer of Madin-Darby canine kidney (MDCK) cells. MDCK cells grown to confluence on porous filters are used to assess trans-epithelial permeability, as determined by the leakage of fluorescein dye through the monolayer.
- MDCK permeability barrier is a model for the outermost layers of the corneal epithelium and this system can therefore be considered to reflect early changes in the development of eye irritation in vivo.
- Disposable lab ware includes: Corning Support Transwell 24-well cell culture plate with microporous membrane, Cat. No. 29445-100 or 29444-580, MFG. No. 3397; Corning Receiver 24-well Tissue Culture Plate, Cat No. 29444-100, MFG. No. 3527; disposable 200 tips Cat. No. 82003-196; Eppendorf 5mL combitips plus Cat No. 21516-152; Sodium Chloride 0.9% (w/v) Aqueous Cat. No. RC72105; and sterile 15mL polypropylene centrifuge tubes.
- Reagents supplied by Life Technologies include: Hank's Balanced Salt Solution (lOx) without Phenol Red Cat. No. 14065056 and Sodium Bicarbonate Solution, 7.5% Cat No. 25080094, Minimum Essential Medium (MEM) (lx), Cat No. 11095072, Fetal Bovine Serum, HI Cat No. 10082147, Antibiotic Antimycotic lOOx Cat No. 15240096, L-Glutamine 200mM (lOOx) Cat No.
- HBSS Hank's Balanced Salt Solution
- the pH should be in the range of 6.8-7.2 and the solution should be warmed to 37C; (2) a 200 ug/mL stock solution of sodium fluorescein in HBSS Buffer; (3) Complete Minimum Essential Medium (MEM) is prepared by combining lOOmL's of Fetal Bovine Serum, lOmL's of Antibiotic Antimycotic lOOx, and lOmL's of L-Glutamine 200mM (lOOx) to lOOOmL's of MEM (lx).
- MEM Complete Minimum Essential Medium
- Permeability of the membrane is confirmed by including a No Cell Control that is run with each day of testing. Sunscreen test compositions are evaluated full strength.
- Inserts are washed to remove cell medium.
- a 24-well cell culture plate Corning Cat No.29445-100, containing a confluent monolayer of MDCK cells is removed from the incubator.
- Each 24-well cell culture plate includes an insert which holds an inner well with a microporous membrane cell growth surface suspended into a lower well.
- the insert containing the cell cultures is washed 5X (BioTek Washer) with warm HBSS to remove culture medium and serum.
- the bottom portion of the 24-well cell culture plate is washed with warm HBSS 3X and on the last wash lmL of HBSS is dispensed in each bottom well.
- 24-well plate can be used to test up to 6 sunscreen test compositions.
- the sunscreen test compositions are added directly to the insert well, Neat (100%), 200 per insert well.
- the 24-well cell culture plate is then returned to the incubator for a 1 hour incubation period.
- the 24-well cell culture plate is removed from the incubator and washed manually to remove test composition. Approximately 200 ⁇ ⁇ of HBSS is added to each inner well and allowed to soak for approximately 1 minute. The test composition and HBSS are then decanted from the individual wells. Any residual sample is removed by delicately flooding the inserts with HBSS and decanting. When the insert is free of residual test composition, a 10X wash (Bio Tek Washer) with warm HBSS should be done. The bottom wells are washed with warm HBSS 3X and on the last wash lmL of HBSS (receiver buffer) is dispensed into each bottom well.
- HBSS HBSS (receiver buffer)
- sodium fluorescein is added to each inner well, 200 ⁇ per well, and the plate is returned to the incubator for a period of 45 minutes.
- the sodium fluorescein containing first plate is removed from the incubator, the upper insert is removed, and the amount of dye that has leaked into the receiver buffer in the lower well is determined by the Powerwave XS microplate reader.
- the fluorescence is read spectrophotometrically at 490nm. Data is printed and recorded.
- the insert is then placed into an empty, temporary, 24 well bottom plate on the Bio Tek Washer for a 10X HBSS wash. Care is taken to ensure that the sodium fluorescein has been washed off and there is no residual fluorescein in the top (inner) or bottom wells.
- the washed insert is placed into a fresh 24-well receiver cell culture plate, Corning
- the 24-well cell culture plate is removed from the incubator.
- the insert containing the cell cultures is washed 5X (BioTek Washer) with warm HBSS to remove culture medium and serum.
- the bottom plate is washed with warm HBSS 3X and on the last wash lmL of HBSS is dispensed in each bottom well (receiver buffer).
- Sodium fluorescein is added to each inner insert well, 200 ⁇ per well, and the plate is reassembled and returned to the incubator for a period of 45 minutes.
- the sodium fluorescein containing plate is removed from the incubator, the insert is removed and discarded, and the amount of dye that has leaked into the lower well is determined by the Powerwave XS microplate reader.
- the fluorescence is read spectrophotometrically at 490nm. Data is printed and recorded.
- the spectrophotometric measurement (fluorescein leakage) value for each of the four repeats of a given sunscreen test composition is used to calculate an average fluorescein leakage value for the sunscreen test composition.
- the average fluorescein leakage value of the four "no cell control" wells is also calculated.
- the Modified TEP Score is calculated by dividing the average fluorescein leakage value of the sunscreen test composition by that of the no cell control.
- TEP test Tchao, R. (1988) Trans-epithelial Permeability of Fluorescein In Vitro as an Assay to Determine Eye Irritants. Alternative Methods in Toxicology 6, Progress in In Vitro Toxicology (ed. A.M. Goldberg), 271.
- compositions of the present invention include UV-absorbing polyesters, are substantially free of non-polymeric UV-absorbing sunscreen agents and were prepared as shown in Table 1 and described below.
- AMIGEL is sclerotium gum, available from Alban Muller International of Hialeah, Florida.
- PHENONIP XB is phenoxyethanol (and) methylparaben (and) ethylparaben (and) propylparaben, available from Clariant of Muttenz, Switzerland.
- PEMULEN TR-2 is Acrylates/C 10-30 Alkyl Acrylate Crosspolymer, available from Noveon/Lubrizol of Wickliffe, Ohio.
- CETIOL CC is Dicaprylyl Carbonate, available from Cognis, now BASF of Ludwigshafen, Germany.
- AMPHISOL is a potassium cetyl phosphate (100% anionic), available from DSM of of Heerlen, Netherlands.
- Emulsiphos is potassium cetyl phosphate (60% anionic) and hydrogenated palm glycerides (40%o) available from Symrise of Teterboro, New Jersey.
- 1 Conventional organic sunscreen package includes 5.5%> homosalte, 2.8%> octisalate, 2.2%> octocrylene, 2.8%> oxybenzone, and 1.7% avobenzone.
- the UV-Absorbing Polyester A used in Example 1 was prepared by
- transesterification reaction of the following monomers: (1) dimerdiol, C 36 H72O, (2) di- trimethylolpropane, C12H2 6 O5, (3) dimethyladipate, and (4) benzenepropanoic acid, 3-(2h- benzotriazol-2-yl)-5-(l, l-dimethylethyl)-4-hydroxy-, methylester, C20H23N3O3.
- the mole ratio of the four monomers (monomer 1 : monomer 2: monomer 3 : monomer 4) was 2.4: 3.1 :4.0:8.0.
- the molecular weight was estimated to be about 4661 Daltons.
- the resulting UV-absorbing polyester was combined with a sufficient amount of dicaprylyl carbonate (CETIOL CC) to form a UV-absorbing polyester solution that was 80% by weight UV- absorbing polyester and 20% by weight dicaprylyl carbonate.
- CETIOL CC dicaprylyl carbonate
- Inventive Examples E1-E3 and Comparative Examples C1-C3 were made by the following process.
- a water phase was prepared by adding water to a main vessel and heating to 80°C with mixing.
- AMIGEL, PEMULEN TR2 and PHENONIP XB were added and mixed until dissolved.
- An oil phase was prepared by charging a vessel with CETIOL CC and mixing. At 60°C UV-Absorbing Polyester A, or the conventional organic sunscreen package blend, respectively, was added.
- AMPHISOL K or EMULSIPHOS was added, and the mixture was heated to about 80°C under mixing. The heated water phase was added to the oil phase with moderate shear. Moderate mixing was continued during cooling.
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Abstract
Description
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Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2876983A CA2876983A1 (en) | 2012-06-28 | 2013-06-18 | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
EP13731625.3A EP2866771A2 (en) | 2012-06-28 | 2013-06-18 | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
IN10997DEN2014 IN2014DN10997A (en) | 2012-06-28 | 2013-06-18 | |
BR112014032712A BR112014032712A2 (en) | 2012-06-28 | 2013-06-18 | composition |
RU2015102540A RU2015102540A (en) | 2012-06-28 | 2013-06-18 | SUN COMPOSITIONS CONTAINING ABSORBING UV RADIATION COMPLEX POLYESTER |
AU2013280910A AU2013280910A1 (en) | 2012-06-28 | 2013-06-18 | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
KR20157001822A KR20150024907A (en) | 2012-06-28 | 2013-06-18 | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
CN201380034706.3A CN104427970A (en) | 2012-06-28 | 2013-06-18 | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
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US13/535,899 US20140004055A1 (en) | 2012-06-28 | 2012-06-28 | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
US13/535,899 | 2012-06-28 | ||
US13/710,546 | 2012-12-11 | ||
US13/710,546 US20140004058A1 (en) | 2012-06-28 | 2012-12-11 | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
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WO2014004171A2 true WO2014004171A2 (en) | 2014-01-03 |
WO2014004171A3 WO2014004171A3 (en) | 2014-10-02 |
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PCT/US2013/046326 WO2014004171A2 (en) | 2012-06-28 | 2013-06-18 | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
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US (2) | US20140004058A1 (en) |
EP (1) | EP2866771A2 (en) |
KR (1) | KR20150024907A (en) |
CN (1) | CN104427970A (en) |
AU (1) | AU2013280910A1 (en) |
BR (1) | BR112014032712A2 (en) |
CA (1) | CA2876983A1 (en) |
IN (1) | IN2014DN10997A (en) |
RU (1) | RU2015102540A (en) |
WO (1) | WO2014004171A2 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140004057A1 (en) | 2012-06-28 | 2014-01-02 | Johnson & Johnson Consumer Companies, Inc. | Sunscreen compositions containing an ultraviolet radiation-absorbing polyester |
US9255180B2 (en) | 2012-06-28 | 2016-02-09 | Johnson & Johnson Consumer Inc. | Ultraviolet radiation absorbing polyethers |
KR102057874B1 (en) | 2012-06-28 | 2019-12-20 | 존슨 앤드 존슨 컨수머 캄파니즈, 인코포레이티드 | Sunscreen compositions containing an ultraviolet radiation-absorbing polymer |
DE102019207780A1 (en) * | 2019-05-28 | 2020-12-03 | Beiersdorf Ag | Cosmetic O / W emulsion with scleroglucan and lipophilic UV filter substances |
DE102019207781A1 (en) * | 2019-05-28 | 2020-12-03 | Beiersdorf Ag | Cosmetic O / W emulsion with scleroglucan and hydrophilic UV filter substances |
DE102019207777A1 (en) * | 2019-05-28 | 2020-12-03 | Beiersdorf Ag | Cosmetic O / W emulsion with scleroglucan |
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CN102026683A (en) * | 2008-05-16 | 2011-04-20 | 帝斯曼知识产权资产管理有限公司 | Sunscreens |
WO2010127987A2 (en) * | 2009-05-04 | 2010-11-11 | Dsm Ip Assets B.V. | Sunscreens |
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2012
- 2012-12-11 US US13/710,546 patent/US20140004058A1/en not_active Abandoned
-
2013
- 2013-06-18 CN CN201380034706.3A patent/CN104427970A/en active Pending
- 2013-06-18 BR BR112014032712A patent/BR112014032712A2/en not_active IP Right Cessation
- 2013-06-18 WO PCT/US2013/046326 patent/WO2014004171A2/en active Application Filing
- 2013-06-18 EP EP13731625.3A patent/EP2866771A2/en not_active Withdrawn
- 2013-06-18 AU AU2013280910A patent/AU2013280910A1/en not_active Abandoned
- 2013-06-18 CA CA2876983A patent/CA2876983A1/en not_active Abandoned
- 2013-06-18 IN IN10997DEN2014 patent/IN2014DN10997A/en unknown
- 2013-06-18 RU RU2015102540A patent/RU2015102540A/en not_active Application Discontinuation
- 2013-06-18 KR KR20157001822A patent/KR20150024907A/en not_active Application Discontinuation
-
2014
- 2014-12-10 US US14/565,968 patent/US20150086495A1/en not_active Abandoned
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US20050036961A1 (en) | 2003-08-13 | 2005-02-17 | Societe L'oreals S.A. | Aesthetically and SPF improved UV-sunscreens comprising glass microspheres |
US20110104078A1 (en) | 2009-11-02 | 2011-05-05 | Inolex Investment Corporation | Uv absorbing complex polyester polymers, compositions containing uv absorbing complex polyester polymers, and related methods |
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BR112014032712A2 (en) | 2017-06-27 |
RU2015102540A (en) | 2016-08-20 |
CA2876983A1 (en) | 2014-01-03 |
US20150086495A1 (en) | 2015-03-26 |
US20140004058A1 (en) | 2014-01-02 |
AU2013280910A1 (en) | 2015-01-22 |
CN104427970A (en) | 2015-03-18 |
WO2014004171A3 (en) | 2014-10-02 |
KR20150024907A (en) | 2015-03-09 |
EP2866771A2 (en) | 2015-05-06 |
IN2014DN10997A (en) | 2015-09-25 |
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