Source: http://www.google.com/patents/US6537529?dq=6317900
Timestamp: 2015-03-01 13:08:16
Document Index: 16052968

Matched Legal Cases: ['Art 1', 'Art 2', 'Art 3', 'Art 3', 'Art 4', 'Art 5', 'Art 6', 'Art 6', 'Art 7']

Patent US6537529 - Sunscreen compositions and methods and materials for producing the same - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsA method of preparing a sunscreen including a solvent system and a filter system, the method including the step of controlling the polarity of the solvent system to control the rate of photodecay of the filter system, as well as sunscreen compositions and compounds for producing sunscreen compositions,...http://www.google.com/patents/US6537529?utm_source=gb-gplus-sharePatent US6537529 - Sunscreen compositions and methods and materials for producing the sameAdvanced Patent SearchPublication numberUS6537529 B1Publication typeGrantApplication numberUS 10/092,131Publication dateMar 25, 2003Filing dateMar 5, 2002Priority dateMar 5, 2002Fee statusPaidPublication number092131, 10092131, US 6537529 B1, US 6537529B1, US-B1-6537529, US6537529 B1, US6537529B1InventorsCraig A. BondaOriginal AssigneeThe C.P. Hall CompanyExport CitationBiBTeX, EndNote, RefManPatent Citations (6), Non-Patent Citations (15), Referenced by (28), Classifications (20), Legal Events (15) External Links: USPTO, USPTO Assignment, EspacenetSunscreen compositions and methods and materials for producing the same
Typically, the above-described UV-B filters are combined with the above-described UV-A filters in a solution with other lipophilic or oily ingredients. This solution of oily ingredients, known to formulators of cosmetic products including sunscreens as the �oil phase,� is typically, but not necessarily, dispersed with the help of emulsifiers and stabilizers into an aqueous solution composed primarily of water, to make an emulsion which becomes a final cream or lotion form of a sunscreen composition.
Disclosed herein are sunscreen compositions and methods of making sunscreen compositions. It has been found that, quite surprisingly, the stability of a photoactive compound is affected by the polarity of a solution of the compound and, hence, in part based on the polarity of the solvent system. Now knowing that the polarity of the solution affects the stability, one might expect that the more polar the solution is, the greater the stability it will impart to the photoactive compound. In contrast, and even more surprisingly, it has been found (for example, with reference to a specific case) that as the polarity of a solvent system including a dissolved, rapidly-photodegradable compound is increased, the rate of photodecay initially decreases�but then increases again as the polarity is further increased. Thus, a photodegradable compound in solution will degrade as a second-order function of the overall polarity of the solution. Currently accepted photochemical theory provides the possibility that the mechanism by which a photodegradable compound is stabilized is the transfer of a photonically-excited electron to a nearby molecule of the same or different species (see, e.g., N. J. Turro, Modern Molecular Photochemistry, Chapter 9, Benjamin/Cummings Publ. Co., Menlo Park, Calif. (1991)), however photochemical theory does not describe the observed phenomena. Though not intending to be bound by such a belief, the observed phenomena are believed to coincide with the electron transfer theory of Professor Rudolph A. Marcus of the California Institute of Technology, for which he received the 1992 Nobel Prize in Chemistry.
The dielectric constant of a solvent system is a preferred measure of polarity of a solvent system, for example because the dielectric constant is a measure of both inherent and inducible dipole moments. Other measures of polarity include, but are not limited to, the induced and/or inherent (permanent) dipole moment (e.g., in Debye units), the Dimroth-Reichardt ET parameter (see, e.g., McNaught et al., Eds., IUPAC Compendium of Chemical Terminology, 2nd. Ed. (1997) and K. Dimroth et al., Justus Liebigs Ann. Chem., vol. 661, p. 1-37 (1963) (German)), ionizing power (see, e.g., T. W. Bentley et al., Adv. Phys. Org. Chem., vol. 14, p. 1-67 (1977); T. W. Bentley et al., Progr. Phys. Org. Chem., vol. 17, p. 121-158 (1990); see also the Grunwald-Winstein equation in E. Grunwald et al., J. Am. Chem. Soc., vol. 70, p. 846-854 (1948) and A. H. Fainberg et al., J. Am. Chem. Soc., vol. 78, p. 2770-2777 (1956), for example), Kamlet-Taft solvent parameters (see, e.g., M. J. Kamlet et al., Progr. Phys. Org. Chem. vol. 13, p. 485-630 (1981)), and the Z-value (see, e.g., E.M. Kosower, J. Am. Chem. Soc., vol. 80, p. 3253-3260 (1958)). See generally, C. Reichardt, �Solvents and Solvent Effects in Organic Chemistry� 2nd ed., Chap. 7: Empirical Parameters of Solvent Polarity, VCH Publishers, New York, N.Y., (1988).
A step of determining the rate constant of photodecay of a mixture or an emulsion also can be performed in various ways. For example, determining a rate constant of photodecay at a selected wavelength can include the steps of measuring absorbance of the mixture of radiation at the selected wavelength before irradiation and after each of a plurality of exposures to radiation at the selected wavelength; and then calculating the rate constant based on the measurements. Absorbance before and after exposure to radiation can be measured by various methods, preferably by the method described in Example 1 below. Other methods are described, for example, in N. Tarras-Wahlberg et al., Changes in Ultraviolet Absorption of Sunscreens After Ultraviolet Radiation, J. Investigative Dermatology, Vol. 113, No. 4, p. 547-553 (October, 1999); R. M. Sayre, Photostability Testing of Avobenzone, Allured's Cosmetics & Toiletries magazine, Vol. 114, No. 5, p. 85-91 (May 1999); and �Photostability of HallStar Photostable SPF 32 Sunscreen Compared to Neutrogena UVA/UVB Sunblock SPF 30,� distributed by Suncare Research Laboratories, Memphis, Tenn. (Oct. 5, 2000), the disclosures of which are hereby incorporated herein by reference.
As used herein, the term �alkyl� includes straight chained and branched hydrocarbon groups containing the indicated number of carbon atoms. typically methyl, ethyl, propyl, and butyl groups. The term �alkyl� also includes �bridged alkyl,� eg., a C4-C16 bicyclic or polycyclic hydrocarbon group, for example, norbomyl, adamantyl, bicyclo[2.2.2]octyl, bicyclo[2.2.1]heptyl, bicyclo[3.2.1]octyl, or decahydronaphthyl. The term �cycloalkyl� is defined as a cyclic hydrocarbon group, e.g., cyclopropyl, cyclobutyl, cyclohexyl, and cyclopentyl.
A mixture of solvent system and filter system, in accordance with one preferred embodiment, are combined with well-known cosmetically-acceptable additives, such as moisturizers, emollients, solvents, co-solvents, lubricants, thickeners, emulsifiers and/or other common cosmetic formulation additives for solubility of sunscreen active compounds, emulsification, thickening and to provide other skin enhancement, e.g., moisturizing properties. The compositions can be produced as oily lotions, gels, solid sticks, emulsions, aerosols, and all other forms of cosmetic compositions. The dielectric constants of various sunscreen additive materials are well known, see, Dielectric Constant Reference Guide of ASI Instruments, Inc., pages 1-64, (http://asiinstruments.com/dc1.html), hereby incorporated herein by reference. The dielectric constants of some sunscreen ingredients at 25� C. are shown in Table 3 below.
13� 3%
10% C12�C15 alkyl
*denotes estimated value �denotes literature value The formulations labeled �Prior Art 1� and �Prior Art 2� were formulated using typical prior art solvents, in typical concentrations. Formulations �A� though �D� were formulated according to the disclosure herein, and resulted in higher dielectric constants of the oil phases.
To prepare slides for testing, a minimum 100 μl of sunscreen composition is drawn or placed into a pipet tip (Justor 1100 DG, set to dispense 100 μl). Using steady, even pressure on the pipettor plunger, the test substance was applied to VITRO-SKIN square in a pattern of at least 50 small dots arranged to cover a 6 cm center of a square. The VITRO-SKIN square was then placed on a foam block, and the test material was spread by finger (covered with a latex glove or finger cot), first in a circular motion, then by a side-to-side motion during which the VITRO-SKIN is deformed by the pressure. The square was then mounted in a slide holder (60 mm�60 mm glassless slide mounts with metal masks by Gepe Management AG, Zug, Switzerland) and allowed to dry for 30-60 minutes.
To test stability, a slide was positioned on the UV transmittance analyzer using registration marks, and a scan of a 1 cm spot on the slide was performed. The slide was then transferred to a holder placed adjacent to the solar simulator and, using a calipers, was positioned such that the beam of UV radiation exiting the solar simulator illuminated the same 1 cm spot on the slide. The following software settings were used: UV-B�290-320 nm; UV-A�320-400 nm; SPF�290-400 nr; Spectral Irradiance; Noon, July 3, Albuquerque, N. Mex.; SPF Spectral Irradiance and Erythermal Effectiveness settings as set by manufacturer. Following an exposure of 5 MED, the slide was again placed in position on the UV transmittance analyzer, and a scan of the exposed spot was performed. The procedure was repeated on the same 1 cm spot on the slide until the desired total radiation dosage was achieved.
To test the predictive value of a method of formulating a sunscreen composition disclosed herein, two additional sunscreen compositions were produced using the same filter system as in Example 1, and parallel dielectric constant and rate constant of photodecay measurements were made. Subsequently, the two new formulations and formulation �C� from Example 1 above were sent to an independent laboratory for SPF testing of each formulation performed on five human subjects. The sunscreen compositions were produced according to the oil phase ingredients and concentrations (formulations) shown in Table 5. below. Dielectric constants and rate constants of photodecay were measured as described in Example 1, and resulted in the values reported in Table 5 below. Formula C from Example 1 is reproduced for convenience of comparison.
*denotes estimated value The formulation labeled �Prior Art 3� was formulated using typical prior art solvents, in typical concentrations. Formulations �C� and �E� were formulated according to the disclosure herein, and resulted in higher dielectric constants of the oil phases.
As shown in the figure, the second-order polynomial fit to the original six data points was highly predictive of the rate constant of photodecay of the two new formulations �Prior Art 3� and �E.� Also, as expected based on the theory described herein, formulations C and E, which had low rate constants of photodecay (near the theoretical minimum), provided SPFs determined in independent testing that were much higher than the prior art formulation.
*denotes estimated value The formulation labeled �Prior Art 4� was formulated using typical prior art solvents, in typical concentrations. Formulations �F� to �H� were formulated according to the disclosure herein, and resulted in higher dielectric constants of the oil phases.
*denotes estimated value �denotes literature value The formulation labeled �Prior Art 5� was formulated using typical prior art solvents, in typical concentrations. Formulations �I� to �K� were formulated according to the disclosure herein, and resulted in higher dielectric constants of the oil phases.
*denotes estimated value �denotes literature value The formulation labeled �Prior Art 6� was formulated using typical prior art solvents, in typical concentrations. Formulation �L� was formulated according to the disclosure herein, and resulted in higher dielectric constant of the oil phase.
As shown in FIG. 5, the second-order polynomial fit to the original four data points was highly predictive of the rate constant of photodecay of the two new formulations �Prior Art 6� and �L.� Also, as expected based on the theory described herein, formulation L, which had a relatively low rate constant of photodecay, provided an SPF determined in independent testing that was much higher than that of the prior art formulation.
*denotes estimated value �denotes literature value The formulation labeled �Prior Art 7� was formulated using a typical prior art solvent, in a typical concentration. Formulations �M� and �N� were formulated according to the disclosure herein, and resulted in higher dielectric constants of the oil phases.
Patent CitationsCited PatentFiling datePublication dateApplicantTitleUS4387089May 18, 1981Jun 7, 1983Givaudan Corporation4-(1,1-Dimethylethyl)-4'-methoxydibenzoylmethaneUS4489057May 12, 1980Dec 18, 1984Merck Patent Gesellschaft Mit Beschraenkter HaftungU.V. Absorbing cosmetic compositionsUS4562067Jan 12, 1984Dec 31, 1985Haarmann & Reimer GmbhUltraviolet radiation absorptionUS5882633Dec 17, 1997Mar 16, 1999Societe L'oreal S.A.Compositions comprising a dibenzoylmethane derivative, a 1,3,5-triazine derivative and an amide compound, and methods of use thereforUS5972324Jan 24, 1997Oct 26, 1999Alzo, Inco.Dimeric urethane compounds derived from monohydric alcohols, generally fatty alcohols, and a diisocyanate.WO2000044340A1Jan 19, 2000Aug 3, 2000Cognis Deutschland GmbhCosmetic and/or pharmaceutical preparationsNon-Patent CitationsReference1"Photostabilty of HallStar Photostable SPF 32 Sunscreen Compared to Neutrogena UVA/UVB Sunblock SPF 30," Suncare Research Laboratories, Memphis, Tennessee (Oct. 5, 2000).2Beckwith, in "The chemistry of amides: Synthesis of amides," Zabicky, J., Ed. Intersience: New York, pp. 73-185 (1970).3Bentley et al., "Medium Effects on the Rates and Mechanisms of Solvolytic Reactions," Adv. Phys. Org. Chem., vol. 14, pp. 1-67 (1977).4Bentley et al., "Yx Scales of Solvent Ionizing Power," Progr. Phys. Org. Chem. , vol. 17, pp. 121-158 (1990).5Dimroth et al., Justus Liebigs Ann. Chem., vol. 661 pp. 1-37 (1963).6Fainberg et al., "Correlation of Solvolysis Rates. III. t-Butyl Chloride in a Wide Range of Solvent Mixtures," J. Am. Chem. Soc., vol. 78 pp. 2770-2777 (1956).7Grunwald et al., "The Correlation of Solvolysis Rates," J. Am. Chem. Soc., vol. 70, pp. 846-854 (1948).8Haslem, "Recent Developments in Methods For the Esterification and Protection of the Carboxyl Group," Tetrahedron, vol. 36, pp. 2409-2433 (1980).9Kamlet et al., "An Examination of Linear Solvation Energy Relationships," Progr. Phys. Org. Chem., vol. 13, pp. 485-630 (1981).10Kosower, "The Effect of Solvent on Spectra. I. A New Empirical Measure of Solvent Polarity Z-Values," J. Am. Chem. Soc.,vol. 80, pp. 3253-3260 (1958).11McNaught et al., "IUPAC Compendium of Chemical Terminology," 2nd Ed. (1997).12Reichardt, "Solvents and Solvent Effects in Organic Chemistry," 2nd Ed., Chap. 7: Empirical Parameters of Solvent Polarity, VCH Publishers, New York, New York (1998).13Sayre et al., "Photostability Testing of Avobenzone," Allured's Cosmetics & Toiletries Magazine, vol. 114, No. 5, pp. 85-91 (May 1999).14Tarras-Wahlberg et al., "Changes in Ultraviolet Absorption of Sunscreens After Ultraviolet Radiation," J. Investigative Dermatology, vol. 113, No. 4, pp. 547-553 (1999).15Turro, Modern Molecular Photochemistry Benjamin/Cummings Publ. Co., Menlo Park, California, pp. 296-361 (1991).Referenced byCiting PatentFiling datePublication dateApplicantTitleUS6770270 *Mar 25, 2002Aug 3, 2004The C.P. Hall CompanyMethods of making and selling a sunscreen compositionUS7014842May 28, 2004Mar 21, 2006Playtex Products, Inc.Sunscreen compositionUS7311896Feb 5, 2004Dec 25, 2007Mmi CorporationNatural sunscreen compositions and processes for producing the sameUS7588702Jan 30, 2008Sep 15, 2009Hallstar Innovations Corp.Photostabilizing electronic excited state energy particularly singlet state energy from UV-absorbing molecule has been found to be readily transferred to alpha-cyanodiphenylacrylate compounds having an alkoxy radical in four position on phenyl rings; increases UV absorbing life of sunscreen agentUS7597825Aug 9, 2007Oct 6, 2009Hallstar Innovations Corp.Photostabilizing electronic excited state energy particularly singlet state energy from UV-absorbing molecule has been found to be readily transferred to alpha-cyanodiphenylacrylate compounds having an alkoxy radical in four position on phenyl rings; increases UV absorbing life of sunscreen agentUS7713519Oct 29, 2008May 11, 2010Hallstar Innovations Corp.Method of quenching electronic excitation of chromophore-containing organic molecules in photoactive compositionsUS7754191Nov 3, 2008Jul 13, 2010Hallstar Innovations Corp.Adding to a polyalkylene naphthalenedicarboxylate or a dialkyl naphthalenedicarboxylate that has been ultraviolet radiated a 3-phenyl-3-(p-alkoxyphenyl)-2-cyanoacrylate to cause the naphthalenedicarboxylate compound to reach an excited state and fluoresceUS7776614Aug 9, 2007Aug 17, 2010Hallstar Innovations Corp.Adding to a polyalkylene naphthalenedicarboxylate or a dialkyl naphthalenedicarboxylate that has been ultraviolet radiated a 3-phenyl-3-(p-alkoxyphenyl)-2-cyanoacrylate to cause the naphthalenedicarboxylate compound to reach an excited state and fluorescenceUS7959834Jul 20, 2010Jun 14, 2011Hallstar Innovations Corp.Alkoxycrylene/metal oxide photostabilized photoactive compositions and methodsUS7964245Jun 27, 2008Jun 21, 2011Hallstar Innovations Corp.UV-absorbing and photostabilizing polymersUS8070989Jul 31, 2009Dec 6, 2011Hallstar Innovations Corp.Photostabilization of retinoids with alkoxycrylene compoundsUS8075808Apr 29, 2009Dec 13, 2011Hallstar Innovations Corp.Method of quenching electronic excitation of chromophore-containing organic molecules in photoactive compositionsUS8133477Sep 4, 2009Mar 13, 2012Hallstar Innovations Corp.Dispersions of inorganic particulates containing alkoxycryleneUS8257687Nov 11, 2011Sep 4, 2012Hallstar Innovations Corp.Photostabilization of coenzyme Q compounds with alkoxycrylene compoundsUS8263050Apr 29, 2009Sep 11, 2012Hallstar Innovations Corp.Method of quenching electronic excitation of chromophore-containing organic molecules in photoactive compositionsUS8263051Apr 5, 2011Sep 11, 2012Hallstar Innovations Corp.Photostabilization of resveratrol with alkoxycrylene compoundsUS8268294Feb 22, 2011Sep 18, 2012Hallstar Innovations Corp.Photostabilization of retinoids with alkoxycrylene compoundsUS8278332Oct 27, 2011Oct 2, 2012Hallstar Innovations Corp.Photostabilization of retinoids with alkoxycrylene compoundsUS8329148Aug 10, 2012Dec 11, 2012Hallstar Innovations Corp.Photostabilization of coenzyme Q compounds with alkoxycrylene compoundsUS8431112Jan 5, 2012Apr 30, 2013Hallstar Innocations Corp.Photostabilization of cholecalciferol with alkoxycrylene compoundsCN101795662BJul 2, 2008Jan 2, 2013默克专利股份有限公司UV filter capsuleEP2025323A1Mar 31, 2008Feb 18, 2009HallStar Innovations Corp.Method of Quenching Electronic Excitation of Chromophore-Containing Organic Molecules in Photoactive CompositionsWO2004110366A2 *May 28, 2004Dec 23, 2004Sun Pharmaceuticals CorpSunscreen compositionWO2009012871A2 *Jul 2, 2008Jan 29, 2009Merck Patent GmbhUv filter capsuleWO2011014371A2Jul 16, 2010Feb 3, 2011Hallstar Innovations Corp.Photostabilization of retinoids with alkoxycrylene compoundsWO2011028320A2Jul 2, 2010Mar 10, 2011Hallstar Innovations Corp.Dispersions of inorganic particulates containing alkoxycryleneWO2012138467A1Mar 19, 2012Oct 11, 2012Hallstar Innovations Corp.Photostabilization of resveratrol with alkoxycrylene compoundsWO2013070398A2Oct 16, 2012May 16, 2013Hallstar Innovations Corp.Photostabilization of coenzyme q compounds with alkoxycrylene compounds* Cited by examinerClassifications U.S. Classification424/59, 424/60, 424/40, 424/401International ClassificationA61Q17/04, A61K8/42, A61K8/35, A61K8/37, A61K8/40Cooperative ClassificationA61K8/40, A61K8/42, A61K8/35, A61Q17/04, A61K8/37, A61K2800/81European ClassificationA61Q17/04, A61K8/35, A61K8/42, A61K8/37, A61K8/40Legal EventsDateCodeEventDescriptionOct 31, 2014REMIMaintenance fee reminder mailedFeb 21, 2012ASAssignmentFree format text: AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT;ASSIGNOR:HALLSTAR INNOVATIONS CORP.;REEL/FRAME:027742/0917Effective date: 20120217Owner name: BANK OF AMERICA, N.A., AS AGENT, ILLINOISAug 26, 2010FPAYFee paymentYear of fee payment: 8Oct 17, 2008XASNot any more in us 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