Source: http://www.google.com/patents/US6518451?dq=5,581,513
Timestamp: 2016-09-27 18:10:54
Document Index: 770145158

Matched Legal Cases: ['art 3', 'art 3', 'art 3', 'art 3', 'art 1', 'art 1']

Patent US6518451 - Diesters of naphthalene dicarboxylic acid - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsA composition containing a diester of a naphthalene dicarboxylic acid having compound formula (I) for photochemically stabilizing dibenzoylmethane derivatives, absorbing UV radiation, imparting gloss and for stabilizing natural hair color and hair dyes against fading, and which can be used to increase...http://www.google.com/patents/US6518451?utm_source=gb-gplus-sharePatent US6518451 - Diesters of naphthalene dicarboxylic acidAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS6518451 B2Publication typeGrantApplication numberUS 09/843,262Publication dateFeb 11, 2003Filing dateApr 26, 2001Priority dateApr 26, 2001Fee statusLapsedAlso published asUS20020192176, WO2002087528A1Publication number09843262, 843262, US 6518451 B2, US 6518451B2, US-B2-6518451, US6518451 B2, US6518451B2InventorsCraig A. Bonda, Peter J. Marinelli, Robert J. Mc MillinOriginal AssigneeHaarmann & ReimerExport CitationBiBTeX, EndNote, RefManPatent Citations (35), Non-Patent Citations (31), Referenced by (34), Classifications (11), Legal Events (11) External Links: USPTO, USPTO Assignment, EspacenetDiesters of naphthalene dicarboxylic acid
US 6518451 B2Abstract
A composition containing a diester of a naphthalene dicarboxylic acid having compound formula (I) for photochemically stabilizing dibenzoylmethane derivatives, absorbing UV radiation, imparting gloss and for stabilizing natural hair color and hair dyes against fading, and which can be used to increase the emolliency and sunscreen protection factor (SPF) of cosmetic formulations and for filtering out ultraviolet radiation from human skin: wherein R1 is has the formula (II) wherein k is 1 to 13, preferably 1 to 6, most preferably 1, and R2, same or different, is selected from the group consisting of a compound of formula (II) wherein k is 1 to 13, preferably 1 to 6, most preferably 1, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms, and mixtures thereof. These diesters of formula (I) are quite effective in stabilizing the dibenzoylmethane derivative UV-A filter compounds making them more effective, and effective for longer periods of time.
What is claimed is: 1. A diester having the formula (I): wherein R1 has the formula (II) wherein k is 1 to 13; and R2 is selected from the group consisting of formula (II) wherein k is 1 to 13, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms.
8. A composition having an SPF of at least 2, for topical application to hair or human skin, in a cosmetically acceptable carrier, comprising at least about 0.1% by weight, based on the total weight of the composition, of a diester of formula (I) wherein R1 has the formula (II) wherein k is 1 to 13, and R2, same or different, is selected from the group consisting of formula (II) wherein k is 1 to 13, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms.
19. A composition, including a carrier selected from the group consisting of water, an organic compound, and mixtures thereof, the improvement comprising about 0.1% to about 20% by weight, based on the total weight of the composition, of a diester of formula (I) wherein R1 has the formula (II) wherein k is 1 to 13; and R2 is selected from the group consisting of formula (II) wherein k is 1 to 13, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms.
31. A method of filtering out ultraviolet radiation from human skin comprising topically applying to said skin a composition, in a cosmetically acceptable carrier, comprising a diester of formula (I) wherein R1 has the formula (II) wherein k is 1 to 13; and R2 is selected from the group consisting of formula (II) wherein k is 1 to 13, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms.
42. A method of stabilizing the color of natural or synthetic dye-containing hair comprising the step of topically applying to said hair a composition, in a cosmetically acceptable carrier, comprising 0.1% to 20% by weight, based on the total weight of the composition, of a diester of formula (I) wherein R1 has the formula (II) wherein k is 1 to 13; and R2 is selected from the group consisting of formula (II) wherein k is 1 to 13, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms.
50. A method of imparting gloss to human hair comprising the step of topically applying to said hair a composition, in a carrier, comprising a diester of formula (I) wherein R1 has for formula (II) wherein k is 1 to 13; and R2 is selected from the group consisting of formula (II) wherein k is 1 to 13, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms.
The UV-A filters most commonly used in commercial sunscreen compositions are the dibenzoylmethane derivatives, particularly 4-(1,1-dimethylethyl)-4′-methoxydibenzoylmethane (PARSOL� 1789), and 4-isopropyl dibenzoylmethane (EUSOLEX 8020). Other dibenzoylmethane derivatives described as UV-A filters are disclosed in U.S. Pat. Nos. 4,489,057; 4,387,089 and 4,562,067 and 5,670,140, hereby incorporated by reference. It is also well known that the above described and most commonly used UV-A filters, particularly the dibenzoylmethane derivatives, such as PARSOL� 1789, suffer in photochemical stability (also called photostability) when used alone or in combination with the above-described most commercially used UV-B filters. Accordingly, when used alone or when combined with a UV-B filter, such as 2-ethylhexyl paramethoxycinnamate (PARSOL� MCX), oxybenzone and/or octyl salicylate, the PARSOL� 1789 becomes less photochemically stable, necessitating repeated, frequent coatings over the skin for sufficient UV radiation protection.
In accordance with one embodiment of the invention, it has been found, quite surprisingly, that by including one or more diesters of naphthalene dicarboxylic acid of formula (I) into a cosmetic sunscreen formulation containing a UV-A dibenzyolmethane derivative, particularly PARSOL� 1789, and/or 4-isopropyl dibenzoylmethane (EUSOLEX 8020), the dibenzyolmethane derivative is photochemically stabilized so that the dibenzyolmethane derivative-containing sunscreen composition, with or without additional sunscreen agents, such as oxybenzone and/or octyl methoxycinnamate (ESCALOL 567), is more effective for filtering out UV-A radiation; the composition filters more UV-A radiation for longer periods of time; and, therefore, the sunscreen formulation need not be applied to the skin as frequently while maintaining effective skin protection against UV-A radiation.
A diester of the invention has the structure (I): wherein R1 has the formula (II), wherein k is 1 to 13, preferably 1 to 6, most preferably 1, and R2, same or different, is selected from the group consisting of a compound of formula (II) wherein k is 1 to 13, preferably 1 to 6, most preferably 1, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms, and mixtures thereof.
The diesters are reaction products of (a) a naphthalene dicarboxylic acid having the structure (III): and an alcohol having the structure R2—OH, wherein R2 is defined as above, or a mixture thereof.
Accordingly, one aspect of the invention is to provide a composition for application to human skin and hair that photochemically stabilizes dibenzoylmethane derivatives, particularly PARSOL� 1789, and capable of increasing the sunscreen protection factor (SPF) achievable for sunscreen compositions containing the dibenzoylmethane derivatives.
Another aspect of the invention is to provide an improved, stable composition containing a diester of a naphthalene dicarboxylic acid that increases the effectiveness of dibenzoylmethane derivative sunscreen compounds, particularly 4-(1,1-dimethylethyl)-4′-methoxydibenzoylmethane (PARSOL� 1789), in SPF and in duration, for protection of human skin and hair.
The preferred compositions of the invention include, optionally, about 0.5% to about 5%, preferably about 0.5% to about 3% of a dibenzoylmethane derivative UV-A filter compound, such as 4-(1,1-dimethylethyl)-4′-methoxydibenzoylmethane (PARSOL� 1789) and about 1% to about 10% by weight of a diester of one or more naphthalene dicarboxylic acid photostabilizer/solubilizer for the dibenzoylmethane derivative, having formula (I): wherein R1 has the formula (II), wherein k is 1 to 13, preferably 1 to 6, most preferably 1, and R2, same or different, is selected from the group consisting of a compound of formula (II) wherein k is 1 to 13, preferably 1 to 6, most preferably 1, and an alkyl group, straight chain or branched, having 1 to 22 carbon atoms, and mixtures thereof.
B (Negative Control)
Percent Loss of
Irradiation (5 MED)
B (negative
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Zatz (pp. 1-8) (http://www-rci.rutgers.edu/˜zatz/SkinPermeation?Retinoids.html.30Zouboulis, Christos C., (Department of Dermatology, University Medical Center Benjamin Franklin, The Free University of Berlin, Berlin, Germany) "Retinoids: Is there a New Approach?", IFSCC Magazine-vol. 3, No. 3 / 2000, pp. 9-19.31Zouboulis, Christos C., (Department of Dermatology, University Medical Center Benjamin Franklin, The Free University of Berlin, Berlin, Germany) "Retinoids: Is there a New Approach?", IFSCC Magazine—vol. 3, No. 3 / 2000, pp. 9-19.Referenced byCiting PatentFiling datePublication dateApplicantTitleUS7014842May 28, 2004Mar 21, 2006Playtex Products, Inc.Sunscreen compositionUS7588702Jan 30, 2008Sep 15, 2009Hallstar Innovations Corp.Method of quenching electronic excitation of chromophore-containing organic molecules in photoactive compositionsUS7597825Aug 9, 2007Oct 6, 2009Hallstar Innovations Corp.Method of quenching electronic excitation of chromophore-containing organic molecules 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