WO2008003090A2 - Formulations avec des glycérides féruloyle et procédés de préparation - Google Patents

Formulations avec des glycérides féruloyle et procédés de préparation Download PDF

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Publication number
WO2008003090A2
WO2008003090A2 PCT/US2007/072557 US2007072557W WO2008003090A2 WO 2008003090 A2 WO2008003090 A2 WO 2008003090A2 US 2007072557 W US2007072557 W US 2007072557W WO 2008003090 A2 WO2008003090 A2 WO 2008003090A2
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WO
WIPO (PCT)
Prior art keywords
product
topical application
feruloyl
acid
different
Prior art date
Application number
PCT/US2007/072557
Other languages
English (en)
Other versions
WO2008003090A3 (fr
Inventor
Louis J. Defilippi
Steven G. Grall
James F. Kinney
Joseph A. Laszlo
David L. Compton
Original Assignee
Biotech Research And Development Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Biotech Research And Development Corporation filed Critical Biotech Research And Development Corporation
Priority to MX2008016455A priority Critical patent/MX2008016455A/es
Priority to BRPI0713966-7A priority patent/BRPI0713966A2/pt
Priority to AU2007264975A priority patent/AU2007264975A1/en
Priority to CA002656091A priority patent/CA2656091A1/fr
Priority to EP07799210A priority patent/EP2040552A2/fr
Publication of WO2008003090A2 publication Critical patent/WO2008003090A2/fr
Publication of WO2008003090A3 publication Critical patent/WO2008003090A3/fr

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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • A61K8/0216—Solid or semisolid forms
    • A61K8/0229—Sticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume 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
    • A61Q19/001—Preparations for care of the lips
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/004—Preparations used to protect coloured hair

Definitions

  • the present invention relates to feruloyl glycerides, their method of preparation, and their use in personal care consumer product applications.
  • Xi and X 2 are the same or different, and at least one of Xi or X 2 is a functional group that bonds with the compound comprising at least one UV-absorbing chromophore, and b+f > 2,
  • Y comprises an O, N, or S that is substituted or unsubstituted, each a, b, c, e and f is > 0 and a+b+c+e+f >2, d is 0 or 1
  • nl and n2 represent the number of hydrogen atoms required to complete the undesignated valencies, and m ranges from 1 to about 100 and each individual m unit may be the same or different, and a topically acceptable agent that is different from the linker agent and the compound comprising at least one UV-absorbing chromophore.
  • Also disclosed herein are products for topical application comprising formulations comprising a fat soluble composition comprising a mono or diacylglycerol esterified with a plant-derived functional group comprising an aromatic species, an unsaturated isoprenoid, an unsaturated terpenoid, a hindered hydroxy-substituted cinnamic acid, an unhindered hydroxy-substituted cinnamic acid or combinations thereof, and a topically acceptable agent that is different from the fat soluble composition.
  • a fat soluble composition comprising a mono or diacylglycerol esterified with a plant-derived functional group comprising an aromatic species, an unsaturated isoprenoid, an unsaturated terpenoid, a hindered hydroxy-substituted cinnamic acid, an unhindered hydroxy-substituted cinnamic acid or combinations thereof, and a topically acceptable agent that is different from the fat soluble composition.
  • Also disclosed herein are products for topical application comprising formulations comprising a fat-soluble composition, comprising a glycerol esterified with a plant- derived functional group comprising maleanilic acid, homovanillic acid, folic acid, crocetin, coumaric acid, caffeic acid, ferulic acid, sinapic acid (sinapinic acid), derivatives thereof or combinations thereof, wherein the esterified glycerol includes at least two plant-derived functional groups, and a topically acceptable agent that is different from fat-soluble composition.
  • products for topical application comprising formulations comprising a chemical composition comprising a linker agent and a compound comprising at least one UV absorbing chromophore, wherein the linker agent is characterized by the general formula:
  • Xi and X 2 are the same or different at least one of Xi or X 2 is a functional group that bonds with the compound comprising at least one UV-absorbing chromophore, and b+f > 2, X3 and X 4 are the same or different and X3, X 4 or both is a hydrophobic moiety, Y comprises an O, N, or S that is substituted or unsubstituted, each a, b, c, e and f is > 0 and a+b+c+e+f >2, d is 0 or 1, nl and n2 represent the number of hydrogen atoms required to complete the undesignated valencies, and m ranges from 1 to about 100 and each individual m unit may be the same or different, and a topically acceptable agent that is different from the linker agent and the compound comprising at least one UV-absorbing chromophore.
  • compositions comprising at least two compounds having the general formula:
  • X 1 H ni X2H n 2 wherein Xi and X 2 are different at least one of Xi or X 2 is a functional group that bonds with a compound comprising at least one UV-absorbing chromophore, and b+f > 2, X 3 and X 4 are the same or different and X3, X 4 or both is a hydrophobic moiety, Y comprises an O, N, or S that is substituted or unsubstituted, each a, b, c, e and f is > 0 and a+b+c+e+f >2, d is 0 or 1, nl and n2 represent the number of hydrogen atoms required to complete the undesignated valencies, m ranges from 1 to about 100 and each individual m unit may be the same or different, and wherein the compound comprising at least one UV-absorbing chromophore comprises a phytochemical which further comprises an aromatic species, an unsaturated isoprenoid, an unsaturated
  • the formulations of the present invention comprise compounds that are described in U.S. Patent Application Serial No. 11/425,094, [Atty. Docket No. 1396-00601], filed June 19, 2006, and entitled “Compositions Comprising A UV- Absorbing Chromophore," and U.S. Patent Application Serial No. 11/425,096, [Atty. Docket No. 1396-00602], filed June 19, 2006, and entitled “Methods of Making Compositions Comprising A UV-Absorbing Chromophore,” both of which are incorporated by reference herein in their entireties.
  • Described below are several product applications for formulations in accordance with the present invention. Each application has been made and tested in blind coded consumer panel samples.
  • the feruloyl glycerides used in accordance with the present invention are lipophilic in nature, with a unique fingerprint of saturated and unsaturated esterif ⁇ ed fatty acids, feruloyl esters and hydroxyl groups. As such, the feruloyl glycerides of the present invention are miscible with many other oil-like substances, have a high kb (kauri butanol) value and solvent power, and have excellent skin and hair absorption and/or penetration characteristics.
  • the feruloyl glycerides of the present invention provide the skin with superior moisture barrier properties, add light reflective or radiance characteristics to dull, dry skin, absorb both Ultra Violet A and B wavelengths of sunlight, offer the skin superior antioxidant protection at various levels within the epidermis, and improve the emollient and dry feel characteristics of the skin.
  • the feruloyl glycerides of the present invention protect colored hair from sun bleaching (i.e. elimination of the color producing chromophore in oxidized dye, such as paraphenylenediamine, plus peroxide), and add conditioning benefits and light reflection to hair.
  • the feruloyl glycerides also help prevent the photodamage that causes all hair types to develop undersirable combing properties after UV exposure.
  • the feruloyl glycerides of the present invention protect lips, skin and hair against environmental damage, and create a synergistic effect with many other cosmetic and over-the-counter (“OTC”) ingredients.
  • Phase A components to main batch tank. Mix using a high shear mixer (e.g. a Lightning Mixer No. 4). Sprinkle thickener (if any) into vortex, created by a mixer. Mix until particles are dissolved or dispersed, while heating to 55 0 C.
  • the feruloyl glyceride in the following examples comprised a family of feruloyl glycerides made from soy. It will be recognized that any feruloyl glyceride derived from any source or in any manner is encompassed within this invention. Feruloyl glyceride can be added to the oil phase ingredients in phase B, in a suitably sized premix vessel, heated and/or mixed until dissolved and/or dispersed, and then added to the main batch (phase A) with mixing.
  • Feruloyl glyceride is an oil based component and has an oily feel at room temperature. Feruloyl glyceride is not water soluble, and it can act as a solvent for ingredients that are difficult to dissolve in water. In some embodiments, it may be desirable to suspend feruloyl glyceride withn a matrix of emulsion or gel. In some embodiments, it may be desirable to obtain an emulsion comprising feruloyl glyceride using a suitable emulsifier.
  • an emulsion in a final product that has a desired viscosity, and to achieve such a desired viscosity, a suitable viscosity modifier may be used.
  • An emulsifier and/or viscosity modifier and/or surfactant can be a topically acceptable agent that is different from the linker agent or the compound comprising at least one UV-absorbing chromophore.
  • the pH of the final product comprising feruloyl glyceride can be any acceptable pH that is compatible with the purpose of the final product.
  • the pH range can be about 2.5 to about 9.0.
  • the pH range can be about 6.0 to about 8.0.
  • the pH range can be about 4.0 to about 6.0.
  • the pH range can be about 2.0 to about 4.0.
  • the final product can be hypoallergenic.
  • Vitamin E and C are well known for their antioxidant properties within the skin and also for the fact that they work together in maintaining a natural defense against radicals. There is a significant amount of scientific evidence that the combination of Vitamin E and C significantly reduced the sunburn reaction to UVb irradiation. There is also evidence of the benefit of applying Vitamin D3 to the skin.
  • the feruloyl glycerides of the present invention are excellent solvents for cholesterol and its derivatives which are excellent skin conditioning agents.
  • Vitamin D3 is easily solubilized as well as other antioxidants, such as Coenzyme Q- 10 [ubiquinone] or Superoxide Dismutase.
  • a chelating agent e.g., ethylenediamine tetraacetic acid ("EDTA")
  • EDTA ethylenediamine tetraacetic acid
  • the arms treated with the feruloyl glycerides of the present invention had far less sunburn and blistering versus the control arm. All panelists verified that they had spent a minimum of 4 total hours in the sun on Saturday and Sunday.
  • the feruloyl glycerides of the present invention are especially well suited to solubilizing sunscreens. Many of these sunscreen ingredients are known to form a powder after skin application as an emulsion and drying. This crystal formation causes a loss in UVb protection as the sunscreens simply flake off after drying. The presence of feruloyl glycerides solubilize all oil soluble sunscreens and create a low melting eutectic which insures that the sunscreens remain fluid, are absorbed into the skin and will not powder on dry down. This provides products with longer lasting sun protection.
  • a 0.5 Carbomer 940 (a viscosity modifier)
  • the feruloyl glycerides of the present invention add excellent conditioning properties to hair conditioner formulations. They are readily absorbed into porous hair which has been treated with chemical services (hair coloring, bleaching, permanent waves, straightening, etc.). After dry down, the hair exhibits excellent shine and luster, manageability and feels silky smooth.
  • the feruloyl glycerides of the present invention are excellent additives for enhancing the long lasting hair colors that are perceived in permanent dyes. They do this by protecting the synthetic hair color from air oxidation and absorb both UVa and UVb ultraviolet rays which damage the color and eliminate the color producing chromophore.
  • hair swatches were colored with one of two commercially available permanent hair coloring products for medium ash brown. Some hair swatches were then wrapped in foil, while other hair swatches were either treated with a conditioner that contained feruloyl glycerides in accordance with the above formulation, or a control formulation that did not contain feruloyl glycerides. The non-foiled hair swatches were then exposed to northern sunlight for 32 hours and then compared to the hair swatches that had been foiled.
  • the hair swatches that had been treated with a conditioner that contained feruloyl glycerides in accordance with the above formulation were much closer in color to the foiled hair swatches than the control formulation that did not contain feruloyl glycerides.
  • a 4 Carnauba Wax (a wax component to build stick structure)
  • a 5 Dimethicone (a silicone to provide shine)
  • Castor Oil (an optional component if color is desired)
  • a major site of sun damage and premature aging is the lip area.
  • the feruloyl glycerides of the present invention show excellent compatibility with lipstick ingredients and provide emolliency, absorption, environmental protection (sun and wind damage), and prevention of transdermal moisture loss.
  • lips were treated with feruloyl glycerides in accordance with the above formulation, and separately treated at a different time with a control formulation that did not contain feruloyl glycerides. Lips that had been treated with feruloyl glycerides in accordance with the above formulation felt better than lips that had been treated with the control formulation that did not contain feruloyl glycerides.
  • Methylparaben and/or Propylparaben (preservatives)
  • Panelists preferred the above shaving formulation containing feruloyl glycerides over a shaving control formulation that did not contain feruloyl glycerides.
  • the feruloyl glycerides of the present invention may be used in skin lightener formulations that carry other active ingredients into the epidermis and thus slow the melanin formation process in age spots.
  • a formulation can be prepared using the formulation of Example 2, adding 1.5% Kojic acid, and reducing the amount of water a corresponding amount, i.e., reduce the amount of water by 1.5%.
  • Kojic acid can be part of Phase B. Kojic acid can penetrate the epidermis and help reduce the production of melanin.
  • a formulation containing feruloyl glycerides was applied to one area of skin having age spots, and a control formulation not containing feruloyl glycerides was applied to another area of skin having age spots.
  • Panelists preferred the formulation containing feruloyl glycerides over the control formulation. Viewing the skin areas after 28 days, 56 days and 84 days showed that skin areas treated with the formulation containing feruloyl glycerides were lighter in color than the skin areas that had been treated with the control formulation.
  • the feruloyl glycerides of the present invention may be incorporated into an anti-aging stick protector to carry peptides into the skin, calling for maximum production of collagen and elastin proteins and minimizing premature degradation of these skin tightening support proteins.
  • Anti-Aging formulations may protect the skin from UVa irradiation from normal sunlight, may alter the skin's moisture retentive characteristics, may add to the skin luminescence, may prevent the excess formation of melanin containing age spots, and may prevent the formation of radicals from UVb and UVa, which then react with other skin ingredients to alter its natural flexibility and tightness.
  • the manufacturing process can involve addition of the liquids to the main batch kettle with mixing. Heat from a jacket kettle can be turned on and the solid ingredients can be added one at a time, until the complete system is melted and solubilized and/or fully dispersed. The hot liquid can then poured in suitable stick molds and allowed to cool and solidify.
  • a 4.0 Beezwax (a was to build a stick structure)
  • Panelists preferred the formulation containing feruloyl glycerides over a control formulation that did not contain feruloyl glycerides. This product is particularly useful to protect skin around the eyes, the skin of the nose, and other portions of the face from sunlight.
  • the feruloyl glycerides of the present invention may be incorporated into a dental cleanser to solubilize dental stains and to flush them away, for example, as part of a dental paste or mouthwash.
  • a 10 Sodium Silicate an abrasive, with larger particles than the sodium silicate used as a
  • Panelists preferred the formulation containing feruloyl glycerides over a control formulation that did not contain feruloyl glycerides.
  • the feruloyl glycerides of the present invention may be used as co-solvent in fragrance compounding.
  • perfumers draw on thousands of scented and fixing compounds which complex with other ingredients within the perfume formulation to achieve the ultimate fragrance interpretation that is desired.
  • the science of perfumery is thousands of years old and normally requires an apprenticeship of 5 years or more with a Master Perfumer to receive accreditation by the American Society of Perfumers.
  • the basic construction of fragrances includes 3 divisions within the fragrance. These are referred to as top, middle and bottom notes.
  • the top notes are light, delicate and quickly volatize at room temperature.
  • the middle notes have more body and require more heat and energy to lift from the skin.
  • the bottom notes of a fragrance form its foundation. They are the heavy lasting notes.
  • fragrance ingredients include terpineol, linalool, benzyl alcohol, benzaldehyde, ylang-ylang and so on. To hold all of these 25-100 ingredients together in a stable solution is no small task. Many times the perfumer feels that they have a stable solution but then there is a formation of one crystal, then another and quickly an avalanche of components falling from what was a clear solution.
  • Diethyl phthalate (DEP), Dioctyl adipate (DOA), and Propylene Glycol are three of the most common solvents used in perfumery by perfumers.
  • the feruloyl glycerides of the present invention bring a totally new dimension to the science of perfumery. It is a useful solvent that takes a broad variety of hydrophobic and some slightly hydrophilic materials into solution.
  • the feruloyl glycerides of the present invention have shown possibilities of forming clathrate structures around fragrances and individual components, which will enhance their stability, performance and resistance to attack.
  • fatty acid ester and ferulic acid ester we see an unexpected synergy of solvent properties, antioxidant characteristics, UVa & b absorbance qualities, skin absorption characteristics, surface activity, and addition to structural type delivery.
  • Fragrances can be made into alcohol solutions, gels, solids, etc. They can be positioned as providing health benefits, anti-aging benefits, environmental protectants, sun protection fragrances as well as many other characteristics. With some hydroxyl substitution and/or ethoxylation on the triglyceride moieties, the molecule can solubilize and/or emulsify hydrophilic materials.
  • the amount of feruloyl glyceride (which is a combination of a linker agent and a compound comprising at least one UV-absorbing chromophore) in a product for topical application as described above can be any suitable range, but is typically about 10% by weight or less of the product.
  • the amount of the combination of a linker agent and a compound comprising at least one UV-absorbing chromophore in a product for topical application is in the range of about 3% to 10% by weight.
  • the amount of a combination of a linker agent and a compound comprising at least one UV-absorbing chromophore is preferably about 5% by weight.
  • the amount of a linker agent and a compound comprising at least one UV-absorbing chromophore is preferably about 8% by weight.
  • the amount of a combination of a linker agent and a compound comprising at least one UV-absorbing chromophore is preferably about 3% by weight.
  • the amount of a combination of a linker agent and a compound comprising at least one UV-absorbing chromophore is preferably about 10% by weight.
  • the amount of a combination of a linker agent and a compound comprising at least one UV-absorbing chromophore is preferably about 4% by weight.
  • the resultant combination incorporates topically acceptable agents other than the linker agent/chromophore such as for feruloyl glyceride in an amount of about 90% by weight or more.
  • the resultant combination comprises a synergistic mixture which is favored and efficacious relative to mixtures which are absent the linker agent/chromophore combination (e.g., feruloyl glyceride).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne un produit pour application topique qui comprend une composition chimique avec un agent liant combiné à un composé incluant au moins un chromophore absorbant les UV, l'agent liant étant caractérisé par la formule générale : [formule chimique] dans laquelle : X1 et X2 sont identiques ou différents et au moins un parmi X1 et X2 est un groupe fonctionnel qui se lie au composé incluant au moins un chromophore absorbant les UV, et b + f ≥ 2 ; Y comprend un O, un N ou un S qui est substitué ou non substitué ; chaque a, b, c, e et f est ≥ 0 et a + b + c + e + f ≥ 2 ; d est 0 ou 1 ; n1 et n2 représentent le nombre d'atomes d'hydrogène requis pour compléter les valences non désignées ; et m est compris entre 1 et environ 100, chaque unité m individuelle pouvant être la même ou différente, et un agent topiquement acceptable qui est différent de l'agent liant et du composé incluant au moins un chromophore absorbant les UV.
PCT/US2007/072557 2006-06-29 2007-06-29 Formulations avec des glycérides féruloyle et procédés de préparation WO2008003090A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
MX2008016455A MX2008016455A (es) 2006-06-29 2007-06-29 Formulaciones con feruloil-gliceridos, y metodos de preparacion.
BRPI0713966-7A BRPI0713966A2 (pt) 2006-06-29 2007-06-29 formulações com feruloil glicerìdeos e métodos de preparação
AU2007264975A AU2007264975A1 (en) 2006-06-29 2007-06-29 Formulations with feruloyl glycerides and methods of preparation
CA002656091A CA2656091A1 (fr) 2006-06-29 2007-06-29 Formulations avec des glycerides feruloyle et procedes de preparation
EP07799210A EP2040552A2 (fr) 2006-06-29 2007-06-29 Formulations avec des glycérides féruloyle et procédés de préparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81753706P 2006-06-29 2006-06-29
US60/817,537 2006-06-29

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WO2008003090A2 true WO2008003090A2 (fr) 2008-01-03
WO2008003090A3 WO2008003090A3 (fr) 2008-05-08

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EP (1) EP2040552A2 (fr)
AU (1) AU2007264975A1 (fr)
BR (1) BRPI0713966A2 (fr)
CA (1) CA2656091A1 (fr)
MX (1) MX2008016455A (fr)
WO (1) WO2008003090A2 (fr)
ZA (1) ZA200810831B (fr)

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Publication number Priority date Publication date Assignee Title
US7572610B2 (en) 2005-10-03 2009-08-11 Biotechnology Research & Development Corporation Methods of making compositions comprising a UV-Absorbing chromophore
US7727514B2 (en) 2005-10-03 2010-06-01 Biotechnology Research & Development Corporation Compositions comprising a UV-absorbing chromophore
WO2012062519A1 (fr) * 2010-11-10 2012-05-18 Evonik Goldschmidt Gmbh Composition comprenant des mélanges d'un amide d'acide isostéarique, d'ester de glycérol et d'eau
WO2016078853A1 (fr) * 2014-11-19 2016-05-26 Beiersdorf Ag Préparations contenant de l'acide ascorbique, de l'ubidécarénone et un mélange émulsifiant

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US6346236B1 (en) * 2000-03-28 2002-02-12 The United States Of America As Represented By The Secretary Of Agriculture Sunscreens from vegetable oil and plant phenols
US6565865B2 (en) * 2001-03-07 2003-05-20 The Procter & Gamble Company Topical composition comprising a three membered cyclic compound-based cosmetic bonding agent
US6890520B2 (en) * 2003-02-05 2005-05-10 Wakayama Prefecture Thermally stable ferulic acid derivatives
US20040258635A1 (en) * 2003-06-17 2004-12-23 Harry-O'kuru Rogers E. Novel sunscreen reagents from unsaturated waxes and triglycerides
US20050096340A1 (en) * 2003-10-29 2005-05-05 Yuehua Zhang Tocopherol-modified therapeutic drug compounds

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7572610B2 (en) 2005-10-03 2009-08-11 Biotechnology Research & Development Corporation Methods of making compositions comprising a UV-Absorbing chromophore
US7727514B2 (en) 2005-10-03 2010-06-01 Biotechnology Research & Development Corporation Compositions comprising a UV-absorbing chromophore
US8357353B2 (en) 2005-10-03 2013-01-22 Biotechnology Research & Development Corporation Compositions comprising a UV-absorbing chromophore
WO2012062519A1 (fr) * 2010-11-10 2012-05-18 Evonik Goldschmidt Gmbh Composition comprenant des mélanges d'un amide d'acide isostéarique, d'ester de glycérol et d'eau
CN103167863A (zh) * 2010-11-10 2013-06-19 赢创高施米特有限公司 包含含有异硬脂酰胺、甘油酯和水的混合物的组合物
US9616007B2 (en) 2010-11-10 2017-04-11 Evonik Degussa Gmbh Composition comprising mixtures of isostearamide, glycerol ester and water
WO2016078853A1 (fr) * 2014-11-19 2016-05-26 Beiersdorf Ag Préparations contenant de l'acide ascorbique, de l'ubidécarénone et un mélange émulsifiant

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EP2040552A2 (fr) 2009-04-01
AU2007264975A1 (en) 2008-01-03
ZA200810831B (en) 2009-10-28
BRPI0713966A2 (pt) 2012-11-27
CA2656091A1 (fr) 2008-01-03
WO2008003090A3 (fr) 2008-05-08
MX2008016455A (es) 2009-05-15

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