WO2021101606A1

WO2021101606A1 - Compositions for sunscreen compounds and methods thereof

Info

Publication number: WO2021101606A1
Application number: PCT/US2020/046864
Authority: WO
Inventors: David Gravett
Original assignee: Pmidg, Llc
Priority date: 2019-11-18
Filing date: 2020-08-18
Publication date: 2021-05-27

Abstract

Disclosed herein are methods of making and using sunscreen compositions comprising at least one UV absorbing e compound and at least one cyclodextrin comprising polymer.

Description

COMPOSITIONS FOR SUNSCREEN COMPOUNDS AND METHODS THEREOF

RELATED APPLICATIONS

[0001] This application claim the benefit under 35 U.S.C. § 119(e) of U.S. Patent Provisional Patent Application Serial No. 62/936,889, filed November 18, 2019, which is herein incorporated in its entirety.

TECHNICAL FIELD

[0002] The present disclosure relates to compositions comprising compounds for reducing the permeation rate of compounds through tissue, particularly for use in topical applications.

BACKGROUND

[0003] More humans are using sunscreen compositions, such as those that reflect ultra-violet (UV) radiation away from exterior surfaces of the body, in greater frequency and for longer periods than was previously known. Humans are applying sunscreens daily, and are using such compositions on all ages, from infants to the elderly. Previously, humans applied sunscreen for outdoor activities on a limited basis. [0004] The longer period of use, by more people, in greater frequency and for years, has led to questions regarding the safety of sunscreen compositions. It was long assumed that the UV-reflective compounds were not absorbed through the skin into the general circulation of the body. But recent studies have shown that such compounds are absorbed by the skin and enter the interior of the body. For example, in 2019, in the Journal of the American Medical Association, Matta et al, describe the results of an exploratory maximal usage trial (MUsT) that studied the systemic absorption (through the skin and into the body) of sunscreen active ingredients using four commercially available sunscreen products. A MUsT study evaluates the systemic absorption of a topical drug (i.e., one applied to the skin) when used according to the maximum limits of the product’s directions for use. In this pilot study, all four active ingredients tested were absorbed from each formulation tested, showing that absorption of sunscreens is not just a theoretical concern. The U.S. Food and Drug Administration (FDA) has issued a proposed rule to update regulatory requirements for most sunscreen products in the United States, where sunscreens are regulated as drugs. As part of this rule, the FDA is requesting additional safety data on 12 active sunscreen ingredients currently available in marketed products because there is no data regarding whether, and to what extent, the ingredient is absorbed into the body after topical application.

[0005] Even with this increased use of sunscreens by humans, the incidence rates of skin cancer continue to rise, with skin cancer remaining the most commonly diagnosed cancer in the United States. This incidence rate makes risk from excess sun exposure an important public health priority. Broad spectrum sunscreens with SPF values of at least 15 are needed for preventing skin cancer and protecting the skin from sunburn and other UV damage. What is needed are formulation compositions, such as sunscreen formulations, comprising at least one UV absorbing compound that is complexed, such that the UV absorbing compound absorption, transmission and/or transport across a body surface barrier is reduced, such that they are slowly absorbed, transmitted and/or transported across body surfaces, such as skin, hair, nails, and mucous membranes.

SUMMARY

[0006] The present disclosure comprises cyclodextrin complexed UV absorbing compounds and formulation compositions comprising at least one UV absorbing compound and at least one or more compound to complex the UV absorbing compound such as cyclodextrin comprising polymers, crosslinked cyclodextrin comprising polymers, or crosslinked cyclodextrins. A cyclodextrin comprising polymer, crosslinked cyclodextrin comprising polymers, or crosslinked cyclodextrin may be referred to herein as a compound to complex the UV absorbing compound. Such cyclodextrin complexed UV absorbing compounds and formulation compositions reflect and/or absorb UV radiation, such as UV-A, UV-B and/or both UV-A and UV-B, and have a reduced absorption rate from the surface of a subject’s body to the interior or circulatory system of the subject’s body as compared to the UV absorbing compound without a cyclodextrin comprising polymer or a crosslinked cyclodextrin comprising polymer.

[0007] In an aspect, a cyclodextrin complexed UV absorbing compounds and formulation compositions comprises a compound to complex the UV absorbing compound such as cyclodextrin. A cyclodextrin is a cyclic oligosaccharide comprising glucose subunits that are joined by a-l,4-glycosidic bonds. The number of subunits in the cyclodextrin structure can vary. Common cyclodextrins include a-cyclodextrin which comprises six glucose subunits, b-cyclodextrin which comprises seven glucose units and g-cyclodextrin which comprises eight glucose units.

[0008] In an aspect, a compound to complex the UV absorbing compound is an oligomer or polymer that comprises a cyclodextrin.

[0009] In an aspect, a compound to complex the UV absorbing compound has the structure shown in Formula (1),

[0011] wherein, CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone and n is an integer and where n is >2.

[0012] In an aspect, a compound to complex the UV absorbing compound has the structure shown in Formula (2),

[0014] wherein, CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone, A is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer and n is an integer and where n is >1, and m is an integer and where m is >1. The structure in Formula (2) can be a block copolymer or it can be a random copolymer.

[0015] In an aspect, a compound to complex the UV absorbing compound has the structure shown in Formula (3),

[0017] wherein CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone, A is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer, B is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer that is different from A, n is an integer and where n is >1, m is an integer and where m is >1, p is an integer and where p is >1 . The structure in Formula (3) can be a block copolymer or it can be a random copolymer.

[0018] In an aspect, D in Formulas 1 to 3 is a residue of a vinyl, acrylate, methacrylate or acrylamide group. Monomers that can be used to for copolymers in Formula (2) and Formula (3) include the monofunctional monomers that can undergo free radical polymerization.

[0019] In an aspect, a compound to complex the UV absorbing compound is a crosslinked cyclodextrin wherein the crosslinked cyclodextrin is formed from the reaction of a cyclodextrin with a multifunctional compound.

FIGURES

[0020] FIG.l shows a graph of differential scanning calorimetry data of an exemplary compound to complex the UV absorbing compound comprising b-cyclodextrin. [0021] FIG.2 shows a graph of differential scanning calorimetry data of an exemplary UV absorbing compound avobenzone.

[0022] FIG.3 shows a graph of differential scanning calorimetry data of the results of an admixture of a compound to complex the UV absorbing compound, beta-cyclodextrin, and a UV absorbing compound, avobenzone.

[0023] FIG.4 shows a graph of differential scanning calorimetry data of an exemplary UV absorbing complexed compound comprising a compound to complex the UV absorbing compound, beta-dextrin, and a UV absorbing compound, avobenzone.

DETAILED DESCRIPTION

[0024] Disclosed herein are cyclodextrin complexed UV absorbing compounds and formulation compositions comprising at least one UV absorbing compound and a compound to complex the UV absorbing compound, and methods for making and using such compositions. As used herein, an UV absorbing compound is a compound that reflects and/or absorbs radiation in certain ultraviolet (UV) wavelengths. Disclosed herein are inorganic compounds that reflect or scatter the light away from the skin, and organic (carbon-based) compounds that absorb UV rays. Some inorganic compounds, including zinc oxide or titanium dioxide, act as a physical sunblock preventing radiation from reaching the body surface as well as absorbing UV radiation. [0025] Examples of organic compounds that are UV absorbing compounds include, but are not limited to cinoxate (CAS 104-28-9), dioxybenzone (CAS 131-53-3), meradimate (CAS 134-09-8), N,N,N-Trimethyl-4-(2-oxoborn-3-ylidenemethyl) anilinium methyl sulphate (CAS 52793-97-2), Benzoic acid, 2-hydroxy-, 3,3,5- trimethylcyclohexyl ester [Homosalate] (CAS 118-56-9), 2-Hydroxy-4- methoxybenzophenone [Oxybenzone] (CAS 131-57-7), 2-Phenylbenzimidazole-5- sulphonic acid [Ensulizole] (CAS 27503-81-7) and its potassium, sodium and triethanolamine salts, 3,3'-(l,4-Phenylenedimethylene) bis (7,7-dimethyl-2- oxobicyclo- [2.2.1] hept-l-ylmethanesulfonic acid) [Ecamsule] (CAS 92761-26-7) and its salts (e.g. CAS 90457-82-2), l-(4-tert-Butylphenyl)-3-(4-methoxyphenyl) propane- 1, 3-dione [Avobenzone] (CAS 70356-09-1), alpha-(2-Oxobom-3-ylidene)toluene-4- sulphonic acid (CAS 56039-58-8) and its salts, 2-Cyano-3, 3-diphenyl acrylic acid 2- ethylhexyl ester [Octocrylene] (CAS 6197-30-4), Polymer of N-{(2 and 4)-[(2- oxoborn-3-ylidene)methyl]benzyl} acrylamide (CAS 113783-61-2), 2-Ethylhexyl 4- methoxycinnamate [Octinoxate] (CAS 5466-77-3), Ethoxylated Ethyl-4- Aminobenzoate (CAS 116242-27-4), Isopentyl-4-methoxycinnamate [Amiloxate] (CAS 71617-10-2), 2,4,6-Trianilino-(p-carbo-2'-ethylhexyl-r-oxy)-l,3,5-triazine (CAS 88122-99-0), Phenol, 2-(2H-Benzotriazol-2-yl)-4-Methyl-6-(2-Methyl-3- (l,3,3,3-Tetramethyl-l-(Trimethylsilyl)Oxy)-Disiloxanyl)Propyl (CAS 155633-54- 8), Benzoic acid, 4,4-{[6-[[[(l,l-dimethylethyl)amino]carbonyl]phenyl]amino]-l,3-5- triazine-2,4-diyl]diimino}bis-, bis(2-ethylhexyl)ester [Iscotrizinol] (CAS 154702-15- 5), 3-(4'-Methylbenzylidene)-dl-camphor [Enzacamene] (CAS 36861-47-9 / 38102- 62-4), 2-Ethylhexyl salicylate [Octisalate] (CAS 118-60-5), 2-Ethylhexyl 4- (dimethylamino)benzoate [Padimate O] (CAS 21245-02-3), 2-Hydroxy-4- methoxybenzophenone-5-sulfonic acid (Benzophenone-5) [Sulisobenzone ] (CAS 4065-45-6 ) and its sodium salt (CAS 6628-37-1), Methylene Bis-Benzotriazolyl Tetramethylbutylphenol (CAS 103597-45-1), Sodium salt of 2,2'-bis(l,4-phenylene)- lH-benzimidazole-4,6-disulfonic acid [Bisdisulizole disodium] (CAS 180898-37-7), 2,2'-(6-(4-Methoxyphenyl)-l,3,5-triazine-2,4-diyl)bis(5-((2-ethylhexyl)oxy)phenol) [Bemotrizinol] (CAS 187393-00-6), Dimethicodiethylbenzalmalonate (CAS 207574- 74-1), Benzoic acid, 2-[4-(diethylamino)-2-hydroxybenzoyl]-hexylester (CAS 302776-68-7), 1,3,5-Triazine, 2,4,6-tris(l,l’-biphenyl)-4-yl-, (CAS 31274-51- 8), and 3, 3 '-(1,4-Phenylene)bis(5, 6-diphenyl- 1, 2, 4-triazine) (CAS 55514-22-2). [0026] Disclosed herein are UV absorbing complexed compounds and formulation compositions comprising at least one UV absorbing compound and a compound to complex the UV absorbing compound, and for example, formulation compositions may comprise topical cosmetic and sunscreen compositions, comprising one or more compounds or molecules that reflect and/or absorb UV-A, UV-B or both UV-A and UV-B radiation, for use in preventing or ameliorating the harmful effects of UV radiation, such as that from the sun. It is desirable that the UV absorbing compounds that are complexed a compound to complex the UV absorbing compound of this disclosure are not significantly absorbed or transported through the body surface, such as skin, and into the general circulation of the body as compared to the uncomplexed UV absorbing compounds. Such compositions that are not significantly absorbed or transported through the body surface, such as skin, and into the general circulation of the body as compared to the uncomplexed UV absorbing compounds are referred to herein as topical, as in topical formulation compositions.

[0027] In an aspect, a compound to complex the UV absorbing compound comprises a cyclodextrin. A cyclodextrin is a cyclic oligosaccharide comprising glucose subunits that are joined by a-l,4-glycosidic bonds. The number of subunits in the cyclodextrin structure can vary. Common cyclodextrins include a-cyclodextrin which comprises six glucose subunits, b-cyclodextrin which comprises seven glucose units and g- cyclodextrin which comprises eight glucose units.

[0028] In an aspect, a compound to complex the UV absorbing compound is an oligomer or polymer that comprises a cyclodextrin.

[0029] In an aspect, a compound to complex the UV absorbing compound has the structure shown in Formula (1),

d) wherein, CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone and n is an integer and where n is >2.

[0030] In an aspect, a compound to complex the UV absorbing compound has the structure shown in Formula (2),

wherein, CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone, A is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer and n is an integer and where n is >1, and m is an integer and where m is >1. The structure in Formula (2) can be a block copolymer or it can be a random copolymer.

[0031] In an aspect, a compound to complex the UV absorbing compound has the structure shown in Formula (3),

wherein CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone, A is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer, B is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer that is different from A, n is an integer and where n is >1, m is an integer and where m is >1, p is an integer and where p is >1 . The structure in Formula (3) can be a block copolymer or it can be a random copolymer.

[0032] In an aspect, D in Formulas 1 to 3 is a residue of a vinyl, acrylate, methacrylate or acrylamide group. Monomers that can be used to for copolymers in Formula (2) and Formula (3) include the monofunctional monomers that can undergo free radical polymerization. Examples of such monomers include but are not limited to those listed in the PolySciences, Inc (Warrington, PA, USA) monomer guide (http://www.polysciences.com/skin/frontend/default/polysciences/pdf/PRINT_Monomer s%20Guide.).

[0033] Specific monomers for polymerizing reactions, which may be linked or added to a cyclodextrin, include but are not limited to the reaction product of a cyclodextrin reacted with glycidyl methacrylate, acyloyl chloride or methacryloyl chloride, and the resulting molecule is referred to herein as cyclodextrin comprising monomer

[0034] In an aspect D-X in Formulas 1 to 3 is -0-C0-CH-CH2-, -0-C0-C(CH3)- CH2-, -NH-CO-C(CH3)-CH2-, -NH-CO-CH-CH2-, -NH-(CH2)n-NH-CO-CH-CH2- where l£n<18, -NH-(CH2)n-NH-CO-C(CH3)-CH2- where l£n<18, -0-CH2- CH(0H)-CH2-0-C0-CH-CH2- or -0-CH2-CH(0H)-CH2-0-C0-C(CH3)-CH2-. [0035] In an aspect, D-X-CD in Formulas 1 to 3 is CD-0-C0-CH-CH2-, CD-O-CO- C(CH3)-CH2-, CD-NH-CO-C(CH3)-CH2-, CD-NH-CO-CH-CH2-, CD-NH-(CH2)n- NH-CO-CH-CH2- where l£n<18, CD-NH-(CH2)n-NH-CO-C(CH3)-CH2- where l£n<18, CD-0-CH2-CH(0H)-CH2-0-C0-CH-CH2- or CD-0-CH2-CH(0H)-CH2- 0-C0-C(CH3)-CH2- where CD is a cyclodextrin. In an aspect the cyclodextrin is a- cyclodextrin. In an aspect, the cyclodextrin is b-cyclodextrin. In an aspect, the cyclodextrin is a g-cyclodextrin. In an aspect the cyclodextrin can comprise a two or more different cyclodextrins.

[0036] In an aspect, the monomer to initiator ratio can be adjusted to change the molecular weight of the produced polymer. The polymer can have a molecular mass of greater than 2,500. In an aspect, the molecular weight of the polymer is greater than 5,000. In an aspect, the molecular weight of the polymer is greater than 10,000. In an aspect, the molecular weight of the polymer is greater than 25,000. In an aspect, the molecular weight of the polymer is greater than 50,000.

[0037] In an aspect, the chemical composition of the monomer as well as the ratios of the monomers to cyclodextrin monomer can be altered such that the resultant polymer is soluble in water or insoluble in water. In an aspect, the chemical composition of the monomer as well as the ratios of the monomers to cyclodextrin monomer can be altered such that the resultant polymer is amphiphilic. In an aspect, the chemical composition of the monomer as well as the ratios of the monomers to cyclodextrin monomer can be altered such that the resultant polymer can be used as an emulsifying agent. In an aspect, the cyclodextrin component is at least 30% (w/w) of the formed polymer. In an aspect, the cyclodextrin component is at least 50% (w/w) of the formed polymer. In an aspect, the cyclodextrin component is at least 70% (w/w) of the formed polymer. [0038] In an aspect, the cyclodextrin comprising monomer can be complexed with the UV absorbing compound prior to the polymerization reaction that forms the polymer. The cyclodextrin comprising monomer can be complexed with the UV absorbing compound in a molar ratio of equal and greater than 0.25 cyclodextrin comprising monomer to 1 UV absorbing compound. In an aspect, the molar ratio of cyclodextrin comprising monomer to UV absorbing compound is greater than 0.5:1. In an aspect, the molar ratio of cyclodextrin comprising monomer to UV absorbing compound is greater than 1:1. In an aspect, the molar ratio of cyclodextrin comprising monomer to UV absorbing compound is greater than 1.5:1. In an aspect, the molar ratio of cyclodextrin comprising monomer to UV absorbing compound is greater than 2:1. In an aspect, the molar ratio of cyclodextrin comprising monomer to UV absorbing compound is about 1:1. In an aspect, the molar ratio of cyclodextrin comprising monomer to UV absorbing compound is about 2:1.

[0039] The cyclodextrin comprising monomer can be found in cyclodextrin comprising polymer compounds comprising crosslinked polymers by incorporating multifunctional monomers into the polymer component (e.g., D in formula 1) of the compound. The multifunctional monomer can comprise two polymerizable groups, three polymerizable groups, four polymerizable groups or greater than 4 polymerizable groups. Multifunctional monomers that can be used include but are not limited to Pentaerythritol triacrylate, Ethylene Glycol Dimethacrylate, Polyethylene glycol dimethacrylate, Ethylene glycol diacrylate, Tetraethylene glycol diacrylate, Pentaerythritol tetraacrylate, 1,4-Phenylene diacrylate, 1,6-Hexanediol diacrylate, 1,4- Butanediol dimethacrylate, 1,6-Hexanediol dimethacrylate, Divinylbenzene, Dipentaerythritol pentaacrylate, Triethylene glycol diacrylate, 1 ,9-Nonanediol dimethacrylate, 1,3-Butanediol dimethacrylate, 1,5-Pentanediol dimethacrylate, Diethylene glycol diacrylate, N,N'-Cystaminebisacrylamide, Diurethane Dimethacrylate, 1,1,1-Trimethylolpropane trimethacrylate, 1,10-Decanediol dimethacrylate, and 2,2-Bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane. The multifunctional monomer can further comprise cyclodextrin. The cyclodextrin multifunctional monomer can include but is not limited to a cyclodextrin comprising at least two acrylate, methacrylate or acrylamide groups. In an aspect, the cyclodextrin multifunctional monomer can comprise 2, 3, 4, 5, 6, 7, or 8 acrylate, methacrylate or acrylamide groups. In an aspect, the cyclodextrin multifunctional monomer is the reaction product of acrylic anhydride and a cyclodextrin. In an aspect, the cyclodextrin multifunctional monomer is the reaction product of methacrylic anhydride and a cyclodextrin. In an aspect, the cyclodextrin multifunctional monomer is the reaction product of glycidyl methacrylate and a cyclodextrin. In an aspect, the cyclodextrin multifunctional monomer is the reaction product of acryloyl chloride or methacryloyl chloride and a cyclodextrin. In an aspect, the cyclodextrin multifunctional monomer is the reaction product of maleic anhydride and a cyclodextrin.

[0040] The cyclodextrin comprising monomer can be complexed with the UV absorbing compound prior to the polymerization reaction that forms the crosslinked polymer. In an aspect, a multifunctional monomer can be incorporated into the formulation such that a crosslinked polymer is obtained. The polymerization can be initiated by heat, light or a redox reaction. In an aspect, an initiator is added to the composition to initiate the polymerization process. The initiator can be a free radical initiator, a UV light initiator or a redox initiator. In an aspect 2 or more initiators can be added to the formulation to bring about the polymerization process. The resultant polymers can be used without further purification. In an aspect, the resultant polymer can be purified. In an aspect, the UV absorbing compound can be formulated with the purified cyclodextrin-comprising polymer such that the UV absorbing compound forms a complex with the cyclodextrin-comprising polymer.

[0041] In an aspect, the compound to complex the UV absorbing compound is a crosslinked matrix, which is also referred to a crosslinked cyclodextrin comprising polymer, as in a polymer of cross-linked cyclodextrin. The crosslinked matrix is prepared by the reaction of a cyclodextrin with a multifunctional compound. The multifunctional compound is able to react with a functional group on the cyclodextrin or a derivative of a cyclodextrin. A multifunctional compound is one that has at least two reactive groups that can react with one or more of the functional groups of a cyclodextrin or a cyclodextrin derivative. The multifunctional compound can react with one or more of the hydroxyl groups of the cyclodextrin. Multifunctional groups that can react with one or more of the hydroxyl groups of the cyclodextrin include but are not limited to compounds comprising two or more carboxylic acids, aldehydes, epoxides, acyl chlorides, anhydrides, isocyanates, or carbonates. Examples of aldehydes include, but are not limited to, difunctional aldehydes, trifunctional aldehydes, tetrafunctional aldehydes and polymeric aldehydes. Examples of a difunctional aldehydes include, but are not limited to, an aliphatic aldehydes and an aromatic aldehydes. Examples of suitable aldehydes include but are not limited to isophthalaldehyde , 2,3-naphthalenedialdehyde, o-phthalaldehyde, glutaric dialdehyde, crocetin dialdehyde, glutaraldehyde, 2-hydroxy-5-methyl-l,3- benzenedicarboxaldehyde, glyoxal, and succinaldehyde, Examples of epoxides include, but are not limited to, difunctional epoxides, trifunctional epoxides, tetrafunctional epoxides and polymeric epoxides. Examples of a difunctional epoxides includes an aliphatic epoxides and an aromatic epoxides. Examples of suitable expoxides include but are not limited to 1,5-hexadiene diepoxide, 1,7-octadiene diepoxide, bisphenol A diglycidyl ether, 2,2-Bis(4-glycidyloxyphenyl)propane, 1,4- butanediol diglycidyl ether, ethylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 4,4'-methylenebis(N,N-diglycidylaniline), resorcinol diglycidyl ether, poly(ethylene glycol) diglycidyl ether, glycerol diglycidyl ether, bisphenol F diglycidyl ether, polypropylene glycol) diglycidyl ether, poly(dimethylsiloxane), diglycidyl ether terminated, bisphenol A propoxylate diglycidyl ether, N,N- Diglycidyl-4-glycidyloxyaniline, Bis[4-(glycidyloxy)phenyl]methane, and Poly(glycidyl methacrylate) and copolymers. Examples of acyl chlorides include, but are not limited to, difunctional acid chlorides, trifunctional acid chlorides, tetrafunctional acid chlorides and polymeric acid chlorides. Examples of a difunctional acid chloride include, but are not limited to, an aliphatic diacid chloride and an aromatic diacid chlorides. An aliphatic diacid chloride can have one to eighteen methylene groups (-CH2-) between the two acid chloride groups. An aliphatic diacid chloride includes but is not limited to malonyl chloride, succinyl chloride, glutaryl chloride, adipoyl chloride, pimeloyl chloride, suberoyl chloride, azelaoyl chloride, dodecanedioyl dichloride sebacoyl chloride, and terephthaloyl chloride. Diacid chlorides also include, but are not limited to, diglycolyl chloride, dimethylmalonyl chloride, diethylmalonyl dichloride, oxalyl chloride, PEG diacid chloride, 2,2'- oxydiacetyl chloride, and 2,5-durandicarbonyl dichloride, Aromatic diacid chloride include but is not limited to azobenzene-4, 4'-dicarbonyl dichloride, 4,4'- biphenyldicarbonyl chloride, isophthaloyl chloride, 4,4'-oxybis(benzoyl chloride), phthaloyl chloride, and terephthaloyl chloride. Multifunction acid chlorides include but are not limited to 1,3,5-benzenetricarbonyl trichloride. Examples of anhydrides include, but are not limited to, difunctional anhydrides, trifunctional anhydrides, tetrafunctional anhydrides and polymeric anhydrides. Anhydrides include but are not limited to glutaric anhydride, maleic anhydride, pyromellitic dianhydride, 3, 3', 4,4'- benzophenonetetracarboxylic dianhydride, bicyclo[2.2.2]oct-7-ene-2, 3,5,6- tetracarboxylic dianhydride, 4,4'-biphthalic anhydride, meso-butane-1, 2,3,4- tetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 4,4'-biphthalic anhydride, 3,4'-biphthalic anhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1, 2,4,5- cyclohexanetetracarboxylic dianhydride, 1 ,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,4,5-cyclohexanetetracarboxylic dianhydride, 1, 2,3,4- cyclopentanetetracarboxylic dianhydride, 3-(carboxymethyl)- 1 ,2,4- cyclopentanetricarboxylic acid 1,4:2, 3-dianhydride, 2-cyclohexylpropan-2-yl methacrylate, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-l,2-dicarboxylic anhydride, 4-(2,5-dioxotetrahydrofuran-3-yl)-l,2,3,4-tetrahydronaphthalene-l,2- dicarboxylic anhydride, diethylenetriaminepentaacetic dianhydride, 2,6- dibromonaphthalene- 1 ,4 , 5 , 8 -tetracarboxy lie dianhydride, 3 , 3 ' ,4 ,4' - diphenylsulfonetetracarboxylic dianhydride, dibromopyromellitic dianhydride, dicyclohexyl-3, 4, 3', 4'-tetracarboxylic dianhydride, ethylenediaminetetraacetic dianhydride, 4,4'-(ethyne-l,2-diyl)diphthalic anhydride, 4,4'-(ethyne-l,2- diyl)diphthalic anhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 4,4'- (hexafluoroisopropylidene)diphthalic anhydride, 4,4'-

(hexafluoroisopropylidene)diphthalic anhydride, 4,4'-(4,4'-isopropylidenediphenoxy) diphthalic anhydride, naphthalene-1, 4, 5, 8-tetracarboxylic dianhydride, naphthalene- 1, 4,5, 8 -tetracarboxy lie dianhydride, 4,4'-oxydiphthalic anhydride, 3, 4'-oxy diphthalic anhydride, 4, 4'-oxy diphthalic anhydride, 3,4,9, 10-perylenetetracarboxy lie dianhydride, pyromellitic dianhydride, 1 ,4-phenylene bis(l,3-dioxo-l,3- dihydroisobenzofuran-5-carboxylate), l,2,3,4-tetramethyl-l,2,3,4- cyclobutanetetracarboxylic dianhydride, and tricyclo[6.4.0.02,7]dodecane-l, 8:2,7- tetracarboxylic dianhydride. Examples of isocyanates include, but are not limited to, difunctional isocyanates, trifunctional isocyanates, tetrafunctional isocyanates and polymeric isocyanates. Examples of a difunctional isocyanates include, but are not limited to, an aliphatic isocyanates and an aromatic diisocyanates. An aliphatic diacid chloride can have one to eighteen methylene groups (-CH2-) between the two isocyanate groups. A diisocyanate includes but is not limited to 3,3'-dichloro-4,4'- diisocyanatobiphenyl, dicyclohexylmethane 4,4'-diisocyanate, 4,4'-diisocyanato-3,3'- dimethylbiphenyl, 1,5-diisocyanatonaphthalene, hexamethylene diisocyanate, isophorone diisocyanate, methylenediphenyl 4,4'-diisocyanate, 1,3-phenylene diisocyanate, 1 ,4-phenylene diisocyanate, tolylene diisocyanate, tolylene-2,4- diisocyanate, tolylene-2, 6-diisocyanate, trimethylhexamethylene diisocyanate, m- xylylene diisocyanate, poly(hexamethylene diisocyanate), trans- 1,4-cyclohexylene diisocyanate, diphenylmethane 4,4'-diisocyanate, polypropylene glycol), tolylene 2,4-diisocyanate terminated, 1,4-diisocyanatobutane, 1,8-diisocyanatooctane, 1,3- bis(l-isocyanato-l-methylethyl)benzene, 3,3'-dimethyl-4,4’-biphenylene diisocyanate, 4,4'-methylenebis(phenyl isocyanate), 4arm peg isocyanate, peg- diisocyanate, tetramethylene diisocyanate, 1-lysine diisocyanate, lysine ethyl ester diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, decamethylene diisocyanate, dodecamethylene diisocyanate, and cyclohexane bis- (methylene isocyanate), and isophorone diisocyanate. Other suitable compounds for crosslinking cyclodextrins include but are not limited to epichlorohydrin, diphenyl carbonate, 1,1’ -carbonyldiimidazole, and triphosgene

[0042] Poly(carboxylic acid) can be used in the process to prepare crosslinked cyclodextrin polymers. Poly (carboxylic acids) are compounds that have two or more carboxylic acids. In an aspect, the poly(carboxylic acid) can have two carboxylic acid groups, three carboxylic acid groups, four carboxylic acid groups, five carboxylic acid groups or greater than five carboxylic acid groups. Poly(carboxylic acids) can include but are not limited to saturated and unsaturated acyclic poly(carboxylic acids), saturated and unsaturated cyclic poly(carboxylic acids), aromatic poly(carboxylic acids), hydroxypoly(carboxylic acids), and polymeric poly(carboxylic acids). Poly(carboxylic acid) compounds include but are not limited to citric acid, succinic acid, carboxysuccinic acid, poly(acrylic) acid and copolymers thereof, poly(methacrylic) acid and copolymers thereof, 1,2,3,4-butanetetracarboxylic acid, maleic acid, citraconic acid, itaconic acid, 1,2,4-Butanetricarboxylic acid, 1,2,3- propane-tricarboxylic acid, aconitic acid, 1,2,3,4-cyclopentanetetracarboxylic acid,

1.2.3.4-cyclobutanetetracarboxylic acid, biphenyl-3, 3 ',5, 5 '-tetracarboxy lie acid,

1.2.4.5-benzenetetracarboxylic acid, mellitic acid, oxydisuccinic acid, and thiodisuccinic acid.

[0043] A process for producing cyclodextrin copolymers using epichlorhydrin has been proposed by Nestle (NETH 6505361) and by Solms and Egli (Helv. Chim. Acta 48, 1225 (1965); U.S. Pat. No. 3,420,788). Similarly, a number of modifications to the epichlorhydrin cross-linking method were also proposed in documents GB 1 244990, Wiedenhof N. et al., Die Starke 21(5), 119-123 (1969), Hoffman J. L., J. Macromol. Sci-Chem., A7(5), 1147-1157 (1973), and in Japanese patents JP-A-58171404 and JP 61283601.

[0044] A process using a dialdehyde, a dibasic acid, a diester, a dibasic acid dichloride, a diepoxide, a diisocyanate or a dihalogenated derivative has been described in U.S. Pat. No. 3,472,835. The methods used to prepare a crosslinked matrix comprising cyclodextrin as described herein are incorporated by reference.

[0045] A process using polyisocyanates in organic aprotic solvents has been disclosed in U.S. Pat. No. 4,917,956, Asanuma H. et al., Chem. Commun., 1971-1972 (1997) and in International patent WO-A-98 22197. The methods used to prepare a crosslinked matrix comprising cyclodextrin as described herein are incorporated by reference.

[0046] A process using ethylene glycol bis(epoxypropyl) ether was disclosed by Fenyvesi E., et al., in the document Ann. Univ. Sci. Budapest, Rolando Eotvos Nominatae, Sect. Chim. 15, 13-22 (1979). A process using other diepoxy compounds has also been described by Sugiura I., et al., in the document Bull. Chem. Soc. Jpn., (62, 1643-1651 (1989)). The methods used to prepare a crosslinked matrix comprising cyclodextrin as described herein are incorporated by reference.

[0047] A process using dibasic carboxylic acid dihalides in an organic solvent was developed in U.S. Pat. No. 4,958,015 and U.S. Pat. No. 4,902,788. The methods used to prepare a crosslinked matrix comprising cyclodextrin as described herein are incorporated by reference.

[0048] A process based on phytic acid, a polyphosphoric acid used to cross-link cyclodextrin by a vacuum heat treatment, has been described in U.S. Pat. No. 5,734,031. The methods used to prepare a crosslinked matrix comprising cyclodextrin as described herein are incorporated by reference.

[0049] A process for preparing crosslinked cyclodextrim polymers using a poly(carboxylic acid) is described in US 6660804 and is incorporated herein by reference.

[0050] In European patent EP-A-0 502 194, Yoshinaga proposed synthesizing cyclodextrin polymers of different natures such as polyurethane, polyurea, unsaturated polyesters, polyesters, polycarbonates, polyamides and polysulphones. Those cyclodextrin-based polymers can also be synthesized by functionalization thereof by polymerizable functional groups such as acryloyl or methacryloyl groups. Such functionalization is followed by polymerization or copolymerization of those derivatives. Such processes have been described in DE-A-4009 825, by Wimmer T., et al., in Minutes Int. Symp. Cyclodextrins, 6.sup.th 106-109, (1992), Ed: Hedges A. L., pub. Sante Paris, by Harada et al., in Macromolecules 9(5), 701-704, (1976) and by Janus L. et al., in Reactive and Functional Polymers (in press). The methods used to prepare a crosslinked matrix comprising cyclodextrin as described herein are incorporated by reference.

[0051] A process using acrylates, acrylic acid and styrene, rendering the cyclodextrin insoluble by emulsion polymerization, has been described in EP-A-0 780 401. The methods used to prepare a crosslinked matrix comprising cyclodextrin as described herein are incorporated by reference.

[0052] Ultrasound can be used as part of the process to manufacture a crosslinked matrix that comprises cyclodextrin. US application 20080213384 describes a process that utilizes ultrasound to manufacture a crosslinked matrix that comprises cyclodextrin and is incorporated herein by reference.

[0053] In an aspect, the crosslinked matrix that comprises cyclodextrin can be prepared using a solid phase technique, melt technique, a solvent technique or a combination thereof. In the solid phase technique, the reagents are mixed together and then stirred until the crosslinking is complete, For the melt techniques, the multifunctional compound and the cyclodextrin are mixed together and heated for a set period of time such that the crosslinked matrix is formed. For the solvent technique, the multifunctional compound and the cyclodextrin are added to a solvent and are allowed to react to form the crosslinked matrix. In an aspect the solvent mixture is heated to increase the rate of formation of the crosslinked matrix.

[0054] The compound to complex the UV absorbing compound such as cyclodextrin used to prepare the crosslinked matrix can be complexed with one or more UV absorbing compounds prior to the polymerization reaction that forms the polymer. The compound to complex the UV absorbing compound such as cyclodextrin can be complexed with the UV absorbing compound in a molar ratio of equal and greater than 0.1 compound to complex the UV absorbing compound such as cyclodextrin comprising monomer to 1 UV absorbing compound. In an aspect, the molar ratio of compound to complex the UV absorbing compound such as cyclodextrin comprising monomer to UV absorbing compound is greater than 0.25:1. In an aspect, the molar ratio of compound to complex the UV absorbing compound such as cyclodextrin comprising monomer to UV absorbing compound is greater than 0.5:1. In an aspect, the molar ratio of compound to complex the UV absorbing compound such as cyclodextrin comprising monomer to UV absorbing compound is greater than 1:1. In an aspect, the molar ratio of compound to complex the UV absorbing compound such as cyclodextrin comprising monomer to UV absorbing compound is greater than 1.5:1. In an aspect, the molar ratio of compound to complex the UV absorbing compound such as cyclodextrin comprising monomer to UV absorbing compound is greater than 2: 1. In an aspect, the molar ratio of compound to complex the UV absorbing compound such as cyclodextrin comprising monomer to UV absorbing compound is about 1 : 1. In an aspect, the molar ratio of cyclodextrin comprising monomer to UV absorbing compound is about 2:1.

[0055] The compounds to complex the UV absorbing compound such as crosslinked compositions of the invention can undergo processing such as milling, micronization, sieving or a combination thereof to produce microparticles or nanoparticles. In an aspect, an emulsion polymerization can be used to prepare crosslinked particles, and such polymerization reactions are known to those of skill in the art.

[0056] In an aspect, the cyclodextrin comprising compound to complex the UV absorbing compound is hydrolytically stable at pH 6.5 to pH 7.5 for a period of at least 6 months..

[0057] UV absorbing compounds absorb UV radiation with a wavelength of less than 400 nm, e.g., from about 200 to about 400 nm. UV absorbing compounds can absorb, for example, UV-A (from 320 to 400 nm), UV-B (from 290 to 319 nm) and/or UV-C (from 200 to 289 nm) light. In an aspect, UV absorbing compounds absorb UV-A and/or UV-B radiation. In an aspect, UV absorbing compounds that absorb UV-A and/or UV-B radiation and deactivate the absorbed radiation energy in a nonradiative manner.

[0058] Disclosed cyclodextrin comprising compounds that can complex the UV absorbing compound may be formed into a particle, a sphere, a hollow sphere, a fiber, a hollow fiber, a micelle or a liposome. In an aspect, a particle, a sphere, a hollow sphere, micelle or a liposome has a mean diameter of less than about 2500 nm. In an aspect, a particle, a sphere, a hollow sphere, micelle or a liposome has a mean diameter of less than about 1000 nm. In an aspect, a particle, a sphere, a hollow sphere, micelle or a liposome has a mean diameter of less than about 750 nm. In an aspect, a particle, a sphere, a hollow sphere, micelle or a liposome has a mean diameter of less than about 500 nm.

[0059] One or more UV absorbing compounds can be complexed with compound to complex the UV absorbing compound such as the polymers comprising cyclodextrin or the crosslinked matrix that comprises cyclodextrin. The polymers comprising cyclodextrin or the crosslinked matrix that comprises cyclodextrin can be complexed with the UV absorbing compound in a molar ratio of equal and greater than 0.1 cyclodextrin units to 1 UV absorbing compound. In an aspect, the molar ratio of cyclodextrin units to UV absorbing compound is greater than 0.25:1. In an aspect, the molar ratio of cyclodextrin units to UV absorbing compound is greater than 0.5:1. In an aspect, the molar ratio of cyclodextrin units to UV absorbing compound is greater than 1 : 1. In an aspect, the molar ratio of cyclodextrin units to UV absorbing compound is greater than 1.5 : 1. In an aspect, the molar ratio of cyclodextrin units to UV absorbing compound is greater than 2: 1. In an aspect, the molar ratio of cyclodextrin units to UV absorbing compound is about 1:1. In an aspect, the molar ratio of cyclodextrin comprising monomer to UV absorbing compound is about 2:1.

[0060] In an aspect, the UV absorbing compound that is complexed is avobenzone. In an aspect, the UV absorbing compound that is complexed is octocrylene. In an aspect, the UV absorbing compounds that are complexed are a mixture of avobenzone and octocrylene. In an aspect, the UV absorbing compound that is complexed is sulisobenzone. In an aspect, the UV absorbing compound that is complexed is ensulizole.

[0061] The UV absorbing compound can be complexed with a compound to complex the UV absorbing compound, for example, the polymers comprising cyclodextrin or the crosslinked matrix that comprises cyclodextrin, using a mechanical mixing process, a solvent based process, a melt process, or a combination of one or more of these processes. In an aspect, methanol, ethanol, isopropanol, acetone, methyl ethyl ketone (MEK), tetrahydrofuran (THF), toluene, water or a combination of one or more of these solvents can be used to enable the complexation of the UV absorbing compound complexed with the polymers comprising cyclodextrin or the crosslinked matrix that comprises cyclodextrin.

[0062] Cyclodextrin complexed UV absorbing compounds disclosed herein can be incorporated into formulation compositions that can be applied to one or more body surfaces, such as a sunscreen, a cosmetic product or a hair product (topical formulation compositions). Sunscreen compositions can include, but are not limited to, daily use sunscreens, water resistant sunscreens, or combinations thereof. Cosmetic compositions can include, but are not limited to, formulations such as a moisturizer, foundation, lip stick, lip gloss, chap stick, concealer, highlighter, blushes, eye shadows, cleansers, toners, serums, anti-aging products, setting sprays or combinations thereof. Hair product compositions include, but are not limited to, shampoos, conditioners, leave-in conditioners, hair mousse, hair gels, hair spray, curling creams, hair waxes, treatment oils, medicated hair treatments or combinations thereof.

[0063] Disclosed formulation compositions comprising cyclodextrin complexed UV absorbing compounds comprising one or more UV absorbing compounds and at least one or more of a compound to complex the UV absorbing compound such as a cyclodextrin comprising polymer or crosslinked cyclodextrin comprising polymer, may be prepared by methods that are well known by a person of ordinary skill in the field of cosmetic formulation. Various forms of formulation compositions are known. These forms include, but are not limited to, solutions, suspensions, emulsions, liposomes, dispersions, particulates or combinations thereof. Product forms for the sunscreen, cosmetic or hair formulation can include but is not limited to solutions, sprays, gels, lotions, creams, mousses, emulsions, sticks, powders, or combinations thereof.

[0064] In an aspect, a formulation composition disclosed herein, e.g., a sunscreen, cosmetic or hair formulation, can be an emulsion. In an aspect, a formulation is an oil- in-water (o/w) emulsion with a continuous water phase and a discontinuous oil phase. A moisturizer or sunscreen lotion is an example of an oil-in-water composition. In an aspect, a formulation is a water-in-oil (w/o) emulsions with a continuous oil phase and a discontinuous water phase. A sunscreen cream formulation composition may be a water-in-oil composition. In an aspect, a cyclodextrin complexed UV absorbing compound can be in the water phase. In an aspect, a cyclodextrin complexed UV absorbing compound can be in the oil phase. In an aspect, a cyclodextrin complexed UV absorbing compound can be in the water phase and the oil phase. In an aspect, a formulation composition can comprise two or more cyclodextrin complexed UV absorbing compounds, for example with one cyclodextrin complexed UV absorbing compound in the water phase and the other cyclodextrin complexed UV absorbing compound in the oil phase. In an aspect, a formulation comprises two or more different cyclodextrin complexed UV absorbing compounds, optionally, with one cyclodextrin complexed UV absorbing compound in the water phase and the other in the oil phase and/or the water phase. In an aspect, a formulation comprises two or more different cyclodextrin complexed UV absorbing compounds with one cyclodextrin complexed UV absorbing compound in the oil phase and the other in the oil phase and/or the water phase. In an aspect, a formulation composition can be prepared with the same UV absorbing compound complexed in two different cyclodextrin comprising compositions. In an aspect, a formulation can be prepared with the two different UV absorbing compounds complexed in compounds to complex the UV absorbing compound that are the same. In an aspect, a formulation can be prepared with the two different UV absorbing compounds complexed in compounds to complex the UV absorbing compounds that are different. In an aspect, the formulation composition can be prepared with three different UV absorbing compounds that are complexed with the compounds to complex the UV absorbing compound comprising cyclodextrin comprising polymers or crosslinked cyclodextrin comprising polymers. In an aspect, the formulation composition can be prepared with three different UV absorbing compounds that are complexed with the compounds to complex the UV absorbing compound comprising cyclodextrin comprising polymers or crosslinked cyclodextrin comprising polymers.

[0065] The compounds to complex the UV absorbing compound comprising cyclodextrin comprising polymer or the crosslinked cyclodextrin comprising polymer can be incorporated into a formulation composition without prior complexation with an UV absorbing compound. In an aspect, two compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers of different compositions can be incorporated into a formulation composition that comprises one or more UV absorbing compounds. [0066] The complex of one or more UV absorbing compounds with a compound to complex the UV absorbing compound such as cyclodextrin comprising polymer or the crosslinked cyclodextrin comprising polymer can comprise at least 10% (w/w) for the final formulation. In an aspect, the complex of one or more UV absorbing compounds with a compound to complex the UV absorbing compound such as cyclodextrin comprising polymer or the crosslinked cyclodextrin comprising polymer can comprise at least 20% (w/w) for the final formulation. In an aspect, the complex of one or more UV absorbing compounds with a compound to complex the UV absorbing compound such as cyclodextrin comprising polymer or the crosslinked cyclodextrin comprising polymer can comprise at least 35% (w/w) for the final formulation. In an aspect, the complex of one or more UV absorbing compounds with a compound to complex the UV absorbing compound such as cyclodextrin comprising polymer or the crosslinked cyclodextrin comprising polymer can comprise at least 50% (w/w) for the final formulation. In an aspect, the complex of one or more UV absorbing compounds with a compound to complex the UV absorbing compound such as cyclodextrin comprising polymer or the crosslinked cyclodextrin comprising polymer can comprise at least 60% (w/w) for the final formulation. In an aspect, the final formulation is a topical sunscreen.

[0067] Oil-in-water emulsions may comprise a water content of about 40% (w/w) to 80% (w/w) of the final formulation. In an aspect, the water content can be about 50% (w/w) to about 70% (w/w) of the final formulation.

[0068] Formulation compositions disclosed herein comprise one or more UV absorbing compounds and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers may comprise an emulsifier. Water-in-oil emulsifiers include, but are not limited to, glyceryl stearate, lecithin, polyglyceryl oleate, sorbitan stearate, glycol stearate, glyceryl oleate, sorbitan oleate, laureth-3, PEG-8 beeswax, glycol distearate, shea butter glycerides, methyl glucose dioleate, hydroxylated lanolin, and emulsifiers sold by Evonik, see Evonik product webpage.

[0069] Oil-in-water emulsifiers include, but are not limited to, ceteareth-20, ceteareth- 25, gum arabic, PEG-7 glyceryl cocoate, PEG-40 hydrogenated castor oil, polysorbate 20, polysorbate 60, polysorbate 80, PEG- 150 distearate, cetearyl alcohol, stearic acid, glyceryl stearate citrate, laneth-16, ceteth-16, oleth-16, steareth-16, stearyl alcohol, emulsifiers sold by Evonik, see Evonik product webpage.

[0070] A formulation composition comprising one or more UV absorbing compounds and at least one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or crosslinked cyclodextrin comprising polymers, may comprise an emollient. Emollients can include but are not limited to petrolatum, silicone oils, castor oil, lanolin, cocoa butter, liquid paraffin, cetyl alcohol, cetearyl alcohol, isopropyl myristate, isopropyl palmitate, shea butter, stearic acid, steryl alcohol, vegetable oil and combinations thereof.

[0071] A formulation composition comprising one or more UV absorbing compounds and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers may comprise a humectant. A humectant can include, but is not limited to, algae extract, aloe vera, aloe vera palmitate, butylene glycol, caprylyl glycol, ethoxy diglycol, glycerin, hexanediol, honey, hyaluronic acid, methyl gluceth-10, pentylene glycol, propanediol, propylene gycol, sorbitol, sucrose cocoate, urea, sodium lactate and combinations thereof.

[0072] A formulation composition comprising one or more UV absorbing compounds and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers may comprise a conditioning agent. Conditioning agents include but are not limited to cocamidopropyl betaine, cocamidopropyl betaine, stearamidopropyl dimethylamine, trioctyldodecyl citrate, trioctyldodecyl citrate, PEG/PPG- 8/3 diisostearate, myristamidopropyl dimethylamine phosphate (and) propylene glycol, polyquatemium-6, polyquatemium-47, polyquaternium-53, polyquaternium-7, polyquatemium-10, polyquaternium-22, polyquatemium-39, polyquaternium-5, acetylated lanolin, cetearyl alcohol (and) cetrimonium bromide, soyamidopropalkonium chloride, cocamidopropyl dimethylamine, isostearamidopropyl dimethylamine, acetamide MEA, isostearamidopropyl laurylacetodimonium chloride (and) propylene glycol, isostearamidopropyl ethyldimonium ethosulfate (and) propylene glycol, starch hydroxypropyl trimonium chloride, PEG-7 amodimethicone, PEG-33 (and) PEG-8 dimethicone (and) PEG- 14, dimethiconol stearate, dimethicone PEG-8 phosphate, silicone quaternium-8, dimethicone PEG-7 cocoate, dimethicone PEG-8 beeswax, and combinations thereof. [0073] A formulation composition comprising one or more UV absorbing compounds and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers may comprise inorganic particulates. Inorganic particles can include but are not limited to glass particles, glass beads, dyes, zinc oxide and titanium dioxide. [0074] A formulation composition comprising one or more UV absorbing compounds and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers may comprise compounds that enhance water resistance of the formulation composition. Compounds that enhance water resistance of a formulation include, but are not limited to, film-forming polymers. Polymers that can be used include but are not limited to dehydroxanthan gum, Dermacryl AQF polymers, Bis-PEG-18methyl ether dimethylsilane, trimethylsiloxysilicate, and butylated PVP (polyvinylpyrrolidone), octylacrylamide/acrylates copolymer, octylacrylamide/acrylate/butylaminoethyl methacrylate copolymer, film forming polymers suitable for use in the present invention include: from National Starch and Chemical Company, AMPHOMER and AMPHOMER LV-71 polymers (octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer), AMPHOMER HC polymer (acrylates/octylacrylamide copolymer) BALANCE 0/55 and BALANCE CR polymers (acrylates copolymer), BALANCE 47 polymer (octylacrylamide/acrylates butylaminoethyl methacrylate copolymer), RESYN 28- 2930 polymer (VA/crotonate/vinyl neodecanoate copolymer), RESYN 28-1310 polymer (VA/Crotonate copolymer), DynamX polymer (polyurethane- 14 (and) AMP- Acrylates copolymer), RESYN XP polymer (acrylates/octylacrylamide copolymer), STRUCTURE 2001 (acrylates/steareth-20 itaconate copolymer) STRUCTURE 3001 (acrylates/ceteth-20 itaconate copolymer), YODOSOL 32A707, YODOSOL GH15, YODOSOL GH32, YODOSOL GH33, YODOSOL GH34, YODOSOL GH35, YODOSOL GH256, YODOSOL GH800, YODOSOL GH810, YODOSOLGH32A707F, YODOSOL GH15F, YODOSOL GH34F, YODOSOL GH800F, YODOSOL GH810F, YODOSOL GH800PF (acrylates copolymer), YODOSOL GH52, YODOSOL GH52-OP (styrene/methacrylamide/acrylates copolymer), YODOSOL GH265 (polyacrylate-2), YODOSOL GH840, YODOSOL GH41F, YODOSOL GH4I (styrene/acrylates copolymer), YODOSOL PUD (polyurethane- 10 (and) PEG- 12 dimethicone (and) alcohol), DERMACYL AQF (acrylates copolymer), DERMACRYL C (proposed: acrylates copolymer) and DERMACRYL 79 and LT polymers (acylates/octyacrylamide copolymer); from ISP, OMNIREZ-2000 (PVM/MA half ethyl ester copolymer), GANTREZ A-425 (butyl ester of PVM/MA copolymer), GANTREZ AN-119 PVM/MA copolymer, GANTREZ ES 225 (ethyl ester of PVM/MA copolymer), GANTREZ ES-425 (butyl ester of PVM/MA copolymer), AQUAFLEX XL-30 (Polyimide-1), ALLIANZ LT- 120 (Acrylates/C 1-2 Succinates/Hydroxyacrylates Copolymer), ALLIANZ OPT (Acrylates/C 12-22 Alkyl Methacrylate Copolymer), STYLEZE CC-10 (PVP/DMAPA Acrylates Copolymer), STYLEZE 2000 (VP/Acrylates/Lauryl Methacrylate Copolymer), STYLEZE W-20 (Polyquatemium-55), ADVANTAGE PLUS (V A/Butyl Maleate/Isobornyl Acrylate Copolymer); from BASF, ULTRAHOLD STRONG (acrylic acid/ethyl acrylate/t-butyl acrylamide), LUVIMER 100 P (t-butyl acrylate/ethyl acrylate/methacrylic acid), LUVIMER 36D (ethyl acrylate/t-butyl acrylate/methacrylic acid), LUVISET PUR (Polyurethane- 1), LUVISET Clear (VP/Methacrylamide/Vinyl Imidazole Copolymer), LUVIFLEX SOFT (Acrylates Copolymer), ULTRAHOLD 8 (Acrylates/Acrylamide Copolymer), LUVIFLEX Silk (PEG/PPG-25/25 Dimethicone/Acrylates Copolymer), LUVISET CAN (VA/crotonate/vinyl neodecanoate copolymer), LUVIMER PR055 (acrylates copolymer); from Amerchol, AMERHOLD DR-25 (acrylic acid/methacrylic acid/acrylates/methacrylates); from Rohm and Haas, ACUDYNE 258 (acrylic acid/methacrylic acid/acrylates/methacrylates/hydroxy ester acrylates), ACUDYNE DHR (acrylates/hydroxy esters acrylates copolymer) ALLIANZ OPT (Acrylates/C 12- 22 Alkyl Methacrylate Copolymer); from Mitsubishi and distributed by Clariant, DIAFORMER Z-301, DIAFORMER Z-SM, and DIAFORMER Z-400 (methacryloyl ethyl betaine/acrylates copolymer), ACUDYNE 180 (Acrylates/Hydroxy esters Acrylates Copolymer), ACUDYNE SCP

(Ethylenecarboxyamide/AMPSA/Methacrylates Copolymer), and the ACCULYN rheological modifiers; from ONDEO Nalco, FIXOMER 40 (acrylates copolymer), FIXOMER A-30 and FIXOMER N-28 (INCI names: methacrylic acid/sodium acrylamidomethyl propane sulfonate copolymer); from Eastman Chemical, Eastman polymer AQ38S and AQ55S (diglycol/CHEM/isophthalates/SIP copolymer); from Interpolymer, vinylpyrrolidone/tricontanyl copolymers available as GANEX WP660 from ISP, SYNTRAN 5009 AND SYNTRAN 5760 (Styrene/ Acrylates/ Ammonium Methacrylate Copolymer), SYNTRAN 5190 (acrylates copolymer), SYNTRAN 5900 and 5902 (polystyrene), SYNTRAN 5903, 5904, 5905 (styrene/acrylates copolymer), SYNTRAN KL-219C (ammonium acrylates copolymer), SYNTRAN PC 5112 (polyacrylate- 16), SYNTRAN PC5208 (polyacrylate- 15), SYNTRAN PC5100 (Poly acrylate-21 and Acrylates/Dimethylaminoethyl Methacrylate Copolymer) SYNTRAN PC5107 and PC5117 (Polyacrylate-18 and Polyacrylate-19), SYNTRAN PC5205 and PC5227 (Polyacrylate-15 and Polyacrylate-17); from Noveon, FIXATE G-100 (AMP-Acrylates/Allyl Methacrylate Copolymer), FIXATE PLUS (Polyacrylates-X), CARBOPOL Ultrez 10 (Carbomer), CARBOPOL Ultrez 20 (Acrylates/C 10-30 Alkyl Acrylates Copolymer), AVALURE AC series (Acrylates Copolymer), AVALURE UR series (Polyurethane-2, Polyurethane-4, PPG- 17/IPDI/DMPA Copolymer); from Index Chemical Company, LEXOREZ TL8 (Trimethylpentanediol/Adipic Acid Copolymer, LEXOREZ TC8 and LEXOREZ TC- 1 (INCI names: Trimethylpentanediol/Adipic Acid/Isononanoic Acid Copolymer), LEXOREZ 200 (Trimethylpentanediol/Adipic Acid/Glycerin Crosspolymer), LEXOREZ 100 (Adipic Acid/Diethylene Glycol/Glycerin Crosspolymer), copolymer of vinylpyrrolidone and a long-chain .alpha.-olefin, such as those commercially available from ISP Specialty Chemicals of Wayne, NJ. as GANEX V220; LEXFILM SUN (polyester-7 (and) neopentyl glycol diheptanoate), LEXFILM SPRAY (polyester-10 (and) propylene glycol dibenzoate); from Dow Corning: DOW CORNING FA 4002 ID SILICONE ACRYLATE (Isododecane (and) Acrylates/Polytrimethylsiloxymethacrylate Crosspolymer), DOW CORNING FA4001 ID SILICONE ACRYLATE (Cyclopentasiloxane (and) Acrylates/Poly trimethylsiloxymethacrylate Copolymer); and any combination of the foregoing hydrogenated dimer dilinoleyl/dimethylcarbonate copolymer, available from Cognis Corporation of Ambler, Pa. as COSMEDIA DC; Film forming polymers can include polymers with no or limited water solubility as described in WO2017048706 and incorporated herein by reference. 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%.

[0075] SPF is often used to show the protective level of a sunscreen composition. SPF is Sun Protection Factor, and refers to how well the sunscreen protects against UVB rays, which can cause sunburn and several types of skin cancer. UVA radiation, penetrates deeper into the skin and can cause premature wrinkling, age spots and can also heighten the risk for some skin cancers. A broad spectrum sunscreen blocks against both UVA and UVB rays, but currently there is no standard for listing UVA absorbing power. Inorganic compounds that deflect sunlight will deflect both UVA and UVB rays.

[0076] It is recommended to use a sunscreen composition that is rated as SPF 15 to 50, as it is unproven that those rated higher than SPF 50 are any more effective that SPF 50. A sunscreen with an SPF of 15 protects against about 93 percent of UVB rays, and one with an SPF of 30 protects against 97 percent of rays, though no composition can block 100 percent of UV rays. A sunscreen composition will not eliminate UV radiation from reaching the body’s surface, and thus, the SPF number refers to approximately the length of time it will take for a person's skin to show radiation damage, such as turning red. A sunscreen composition with an SPF of 15 will prevent Caucasian skin from getting red for approximately 15 times longer than skin that is not coated with the sunscreen composition. For example, if the skin starts to bum (turning red) in 10 minutes, a sunscreen composition with SPF 15 will prevent burning for about 150 minutes, or 2.5 hours.

[0077] A formulation composition disclosed herein may comprise one or more UV absorbing compounds and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers. In an aspect, an UV absorbing compound is present in an amount effective to provide a SPF of about 10 or greater. In an aspect, the amount of one or more UV absorbing compounds in a formulation composition may vary from about 4% (w/w) to about 60% (w/w) of the final formulation. In an aspect, the amount of one or more UV absorbing compounds present in a formulation can be from about 6% (w/w) to about 40% (w/w) of the final formulation. In an aspect, the amount of one or more UV absorbing compounds in a formulation can be from about 6% (w/w) to about 25% (w/w) of the final formulation.

[0078] Formulation compositions, such as sunscreen, cosmetic and hair compositions disclosed herein can comprise components, that include, but are not limited to, antioxidants, binders, biological additives, buffering agents, colorants, thickeners, polymers, astringents, fragrance, humectants, opacifying agents, conditioners, exfoliating agents, pH adjusters, preservatives, natural extracts, essential oils, skin sensates, skin soothing agents, skin healing agents, SPF boosting agents or combinations thereof. In an aspect, the SPF boosting agent may be an agent that can reflect or refract UV light. In an aspect, the SPF boosting agent may be a hollow particle, a hollow sphere, a hollow fiber, a porous particle, a porous sphere or a porous fiber. In an aspect, the SPF boosting agent may comprise a polymer. In an aspect, the polymer may be a degradable polymer or a non-degradable polymer. In an aspect, the polymer may be a styrene/acrylate co-polymer. In an aspect, the preservative used is, but is not limited to, methylparaben, ethylparaben, propylparaben, butylparaben, germaben phenoxyethanol, methylisothiazolinone, and Iodopropynyl Butylcarbamate [0079] A sunscreen formulation can comprise one or more UV absorbing compounds, one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers and at least one or more of the ingredients selected from the group of Acrylates/clO-30 Alkyl Acrylate Crosspolymer, Acrylates/cl 2-22 Alkyl Methacrylate Copolymer,

Acrylates/dimethicone Copolymer, Adipic Acid/diethylene Glycol/glycerin Crosspolymer, Aluminum Starch Octenylsuccinate, Arachidyl Alchohol, Arachidyl Glucoside, Artemia Extract, Beeswax, Behenyl Alcohol, Benzyl Alcohol, BHT, Bisabolol, Butyloctyl Salicylate, Camellia Sinensis Leaf Extract, Caprylyl Glycol, Caprylyl Methicone, Cetearyl Alcohol, Cetearyl Glucoside, Cetyl Dimethicone, Chlorphenesin, Cyclopentasiloxane, Diethylhexyl 2,6- Naphthalate, Dimethicone, Dimethicone/peg-10/15 Crosspolymer, dicaprylyl ether, Dimethiconol, Dipotassium Glycyrrhizate, Disodium EDTA, Ethylhexyl Stearate, Ethylhexylglycerin, Ethylparaben, Ethylthexlglycerin, ethylhexyl isononanoate, Fragrance, Glycerin, Glyceryl Stearate, Iodopropynyl Butylcarbamate, Isododecane,

Methylisothiazolinone, Methylparaben, Neopentyl Glycol Diheptanoate, Niacinamide, Octadecene/ma Copolymer, Palmitic Acid, PEG 100 Stearate, PEG- 100 Stearate, Phenoxyethanol, Polyester-27, Polymethylsilsesquioxane, Polyvinylpyrrolidone, Potassium Cetyl Phosphate, Potassium Hydroxide, Propylparaben, Saccharomyces/calcium Ferment, Saccharomyces/magnesium Ferment, Saccharomyces/potassium Ferment, Saccharomyces/sodium Ferment, Saccharomyces/zinc Ferment, SD alcohol 40-B, Silica, Sodium Ascorbyl Phosphate, Sodium Polyacrylate, Sodium Polyacrylate Starch, Stearic Acid, Styrene/acrylates Copolymer, Styrene/Acrylates Copolymer Glycerin, Tapioca Starch, Tocopherol (Vitamin E), Tocopheryl Acetate, Trideceth-6, Triethanolamine, Trimethylsiloxysilicate, Trisiloxane, Vp/hexadecane Copolymer, Xanthan Gum, 2- Hexanediol, Glyceryl Stearate, and Water. In an aspect, the UV absorbing compound is avobenzone. In an aspect, the UV absorbing compound is homosalate. In an aspect, the UV absorbing compound is octisalate. In an aspect, the UV absorbing compound is octocrylene. In an aspect, the UV absorbing compounds are avobenzone and octocrylene. In an aspect, the UV absorbing compounds are avobenzone, octocrylene and homosalate. In an aspect, the UV absorbing compounds are avobenzone, octocrylene, octisalate and homosalate. In an aspect, the avobenzone content of the formulation is about 1 to about 5% (w/w). In an aspect, the avobenzone content of the formulation is about 3% (w/w). In an aspect, the octocrylene content of the formulation is about 1 to about 10% (w/w). In an aspect, the octocrylene content of the formulation is about 2 to about 8% (w/w). In an aspect, the homosalate content of the formulation is about 5 to about 10% (w/w). In an aspect, the homasalate content of the formulation is about 7 to about 10% (w/w). In an aspect, the crosslinked cyclodextrin comprising polymer in the sunscreen formulation is diphenyl carbonate crosslinked b- cyclodextrin. In an aspect, the compound to complex the UV absorbing compound such as crosslinked cyclodextrin comprising polymer in the sunscreen formulation is carbonyldiimidazole crosslinked b-cyclodextrin. In an aspect, the compound to complex the UV absorbing compound such as crosslinked cyclodextrin comprising polymer in the sunscreen formulation is epichlorohydrin crosslinked b-cyclodextrin. In an aspect, the compound to complex the UV absorbing compound such as crosslinked cyclodextrin comprising polymer in the sunscreen formulation is a toluene diisocyanate crosslinked b-cyclodextrin. In an aspect, the compound to complex the UV absorbing compound such as crosslinked cyclodextrin comprising polymer in the sunscreen formulation is a 1 ,6-hexamethylene diisocyanate crosslinked b- cyclodextrin. In an aspect, the compound to complex the UV absorbing compound such as crosslinked cyclodextrin comprising polymer in the sunscreen formulation is a pyromellitic dianhydride crosslinked b-cyclodextrin. In an aspect, the compound to complex the UV absorbing compound such as crosslinked cyclodextrin comprising polymer in the sunscreen formulation is a 1,2,3,4-butanetetracarboxylic dianhydride crosslinked b-cyclodextrin. In an aspect, the compound to complex the UV absorbing compound such as crosslinked cyclodextrin comprising polymer in the sunscreen formulation is a citric acid crosslinked b-cyclodextrin In an aspect, the compound to complex the UV absorbing compound such as cyclodextrin comprising polymer in the sunscreen formulation is a methacrylated b-cyclodextrin based polymer. In an aspect, the compound to complex the UV absorbing compound such as cyclodextrin comprising polymer in the sunscreen formulation is an acrylated b-cyclodextrin based polymer.

[0080] The compositions comprising at least one UV absorbing compound and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers have the ability to reduce the rate at which the UV absorbing compound is able to penetrate through a skin sample as measured using a Franz diffusion cell as compared to a composition that does not comprise one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers. In an aspect, incorporation of one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers into a composition that comprises at least one UV absorbing compound, reduces the rate of penetration of the UV absorbing compound through a skin sample in a Franz cell by at least 5% as compared to the composition without one or more cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers. In an aspect, incorporation of one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers into a composition that comprises at least one UV absorbing compound, reduces the rate of penetration of the UV absorbing compound through a skin sample in a Franz cell by at least 50% as compared to the composition without one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers. In an aspect, incorporation of one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers into a composition that comprises at least one UV absorbing compound, reduces the rate of penetration of the UV absorbing compound through a skin sample in a Franz cell by at least 100% as compared to the composition without one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers.

[0081] In determining the UV absorption characteristics of a sunscreen, an important parameter is the critical wavelength of the sunscreen. The critical wavelength is identified as the wavelength at which the integral of the spectral absorbance curve reaches 90 percent of the integral over the UV spectrum from 290 to 400 nm. In an aspect, the sunscreen formulation compositions of the current invention have a mean critical wavelength of 350 nm or greater. In an aspect, the sunscreen compositions of the current invention have a mean critical wavelength of 370 nm or greater. In an aspect, the sunscreen compositions of the current invention have a mean critical wavelength of about 365nm to about 380 nm. In an aspect, the sunscreen compositions of the current invention have a mean critical wavelength of about 370nm to about 390 nm.

[0082] As defined in FDA document 21CFR352.76, the composition can be water resistant or very water resistant. In an aspect, according to FDA document 21CFR201.327, the composition can be water resistant (40 minutes) or water resistant (80 minutes).

[0083] Formulation compositions, such as sunscreen, cosmetic and hair compositions disclosed herein can have a pH that is from about 4.0 to about 8.0, or such as from about 5.5 to about 7.0.

[0084] Cyclodextrin complexed UV absorbing compound compositions and formulation compositions can be used to ameliorate the effects of UV radiation on body surfaces, particularly human and animal skin surfaces. For example, an effective amount of a formulation composition disclosed herein comprising a UV absorbing compounds and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers is applied to the skin in an amount and frequency to provide at least SPF 15 protection for human or animal skin. For applications in cosmetic products, the compositions of the disclosure can have a SPF of greater than 2 but less than 15. [0085] The present disclosure comprises a kit comprising a formulation composition comprising an UV absorbing compounds and one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or the crosslinked cyclodextrin comprising polymers disclosed herein, contained within a container. The kit may further comprise written instructions for its use. In an aspect, the container comprises a plastic. In an aspect the container comprises a screw on lid. In an aspect, the container comprises a flip top lid.

[0086] The compositions and kits of the current disclosure may further comprise an unmodified cyclodextrin. In an aspect, the cyclodextrin is b-cyclodextrin. The compositions and kits of the current disclosure can comprise an unmodified cyclodextrin without a cyclodextrin comprising polymer or a crosslinked cyclodextrin comprising polymer. In an aspect, the cyclodextrin is b-cyclodextrin.

[0087] Disclosed herein are compositions, methods, and kits comprising one or more UV absorbing compound and at least one or more compounds to complex the UV absorbing compound such as cyclodextrin comprising polymers or crosslinked cyclodextrin comprising polymers compositions.

[0088] EXEMPLARY EMBODIMENTS

[0089] The present disclosure provides the following numbered aspects, which are only exemplary and not exhaustive of the aspects provided in the various aspects disclosed herein.

1) A cyclodextrin complexed UV absorbing compound formulation composition comprising at least one compound to complex the UV absorbing compound such as cyclodextrin comprising polymer, at least one UV absorbing compound, a water phase and an oil phase.

2) A cyclodextrin complexed UV absorbing compound formulation composition comprising a crosslinked cyclodextrin comprising polymer, at least one UV absorbing compound, a water phase and an oil phase.

3) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-2 wherein the cyclodextrin is b-cyclodextrin.

4) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-3 wherein the UV absorbing compound is avobenzone.

5) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-3 wherein the UV absorbing compounds are avobenzone and octocrylene. 6) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-5 wherein the avobenzone is about 2% to about 5% (w/w) of the composition.

7) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-6 wherein the avobenzone is about 2% to about 5% (w/w) of the composition and the octocrylene is about 2 to 11 % (w/w) of the composition.

8) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-7 wherein the composition comprises a preservative.

9) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-8 wherein the preservative is methylparaben, ethylparaben or propylparaben.

10) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-8 wherein the preservative is phenoxyethanol.

11) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-8 wherein the preservative is methylisothiazolinone.

12) The cyclodextrin complexed UV absorbing compound formulation composition of embodiments 1-11 wherein the composition is an emulsion.

13) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-12 wherein the composition is a sunscreen

14) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-13 wherein the composition has a SPF of greater than 15

15) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-14 wherein the mean critical wavelength is greater than 360 nm.

16) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-14 wherein the mean critical wavelength is greater than 370 nm.

17) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-16 wherein the composition is water resistant

18) The cyclodextrin complexed UV absorbing compound formulation compositions of aspects 1-17 wherein the composition is water resistant for 40 minutes. 19) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-18 wherein the composition further comprises an unmodified cyclodextrin.

20) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-19 wherein the cyclodextrin is b-cyclodextrin.

21) The cyclodextrin complexed UV absorbing compound formulation composition of aspects 1-20 wherein the cyclodextrin comprising polymer and the UV absorbing compound comprise 10 to 50% (w/w) of the final composition

22) The cyclodextrin complexed UV absorbing compound formulation composition of embodiments 1-20 wherein the compound to complex the UV absorbing compound such as crosslinked cyclodextrin comprising polymer and the UV absorbing compound comprise 10 to 50% (w/w) of the final composition.

23) A kit comprising the aspects 1-22 wherein the kit comprises a container.

24) A kit comprising aspects 1-23 wherein the container comprises a polymer.

25) A kit comprising aspects 1-24 wherein the kit comprises a label with the wording “broad spectrum”.

26) A kit comprising aspects 1-25 wherein the kit comprises a label with the wording “water resistant (40 minutes)”.

27) A kit comprising aspects 1-24 wherein the kit comprises a label with the wording “water resistant (80 minutes)”.

[0090] Disclosed herein are cyclodextrin compositions and topical formulation compositions comprising at least one a cyclodextrin complexed UV absorbing compound comprising one or more UV absorbing compounds and at least one or more compounds to complex the UV absorbing compound, wherein the compound to complex the UV absorbing compound is selected from the group consisting of cyclodextrin comprising polymers, crosslinked cyclodextrin comprising polymers, and crosslinked cyclodextrins. A cyclodextrin comprising polymers may comprise

wherein, CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone and n is an integer and where n is >2. In an aspect, a cyclodextrin comprising polymers may comprise

[0093] wherein, CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone, A is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer and n is an integer and where n is >1, and m is an integer and where m is >1, the copolymer may be a block copolymer or a random copolymer. A cyclodextrin comprising polymers may comprise,

[0095] wherein CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone, A is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer, B is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer that is different from A, n is an integer and where n is >1, m is an integer and where m is >1, p is an integer and where p is >1. The copolymer may be a block copolymer or a random copolymer. In some aspects, shown above, D may be a residue of a vinyl, acrylate, methacrylate or acrylamide group. A formulation composition disclosed herein may comprise a compound to complex the UV absorbing compound comprising crosslinked cyclodextrin comprising polymers. Cyclodextrin compounds to complex the UV absorbing compound may be formed from one or more of alpha cyclodextrin, beta cyclodextrin or gamma-cyclodextrin. A compound or formulation composition disclosed herein may comprise crosslinked cyclodextrin comprises cylclodextrin crosslinked with a crosslinker selected from the group consisting of a diacid, a diisocyanate, epichlorohydrin, diphenyl carbonate, I,G-carbonyldiimidazole, and triphosgene.

[0096] A formulation composition disclosed herein may comprise at least one UV absorbing compound that is selected from the group comprising cinoxate, dioxybenzone, meradimate, N,N,N-Trimethyl-4-(2-oxobom-3-ylidenemethyl) anilinium methyl sulphate, benzoic acid, 2-hydroxy-, 3,3,5-trimethylcyclohexyl ester [Homosalate], 2-Hydroxy-4-methoxybenzophenone [Oxybenzone], 2- Phenylbenzimidazole-5-sulphonic acid [Ensulizole], and its potassium, sodium and triethanolamine salts, 3,3'-(l,4-Phenylenedimethylene) bis (7,7-dimethyl-2- oxobicyclo- [2.2.1] hept-l-ylmethanesulfonic acid) [Ecamsule] and its salts, l-(4-tert- Butylphenyl)-3-(4-methoxyphenyl) propane-1, 3-dione [Avobenzone], alpha-(2- Oxoborn-3-ylidene)toluene-4-sulphonic acid and its salts, 2-Cyano-3, 3 -diphenyl acrylic acid 2-ethylhexyl ester [Octocrylene], Polymer of N-{(2 and 4)-[(2-oxobom- 3-ylidene)methyl]benzyl } acrylamide, 2-Ethylhexyl 4-methoxycinnamate [Octinoxate], Ethoxylated Ethyl-4- Aminobenzoate (CAS 116242-27-4), Isopentyl-4- methoxycinnamate [Amiloxate], 2,4,6-Trianilino-(p-carbo-2'-ethylhexyl-r-oxy)- 1,3,5-triazine, Phenol, 2-(2H-Benzotriazol-2-yl)-4-Methyl-6-(2-Methyl-3-(l,3,3,3- Tetramethyl-l-(Trimethylsilyl)Oxy)-Disiloxanyl)Propyl, Benzoic acid, 4,4-{[6- [[[(l,l-dimethylethyl)amino]carbonyl]phenyl]amino]-l,3-5-triazine-2,4- diyl]diimino}bis-, bis(2-ethylhexyl)ester [Iscotrizinol], 3-(4'-Methylbenzylidene)-dl- camphor [Enzacamene], 2-Ethylhexyl salicylate [Octisalate], 2-Ethylhexyl 4- (dimethylamino)benzoate [Padimate O], 2-Hydroxy-4-methoxybenzophenone-5- sulfonic acid (Benzophenone-5) [Sulisobenzone] and its sodium salt, Methylene Bis- Benzotriazolyl Tetramethylbutylphenol, Sodium salt of 2,2'-bis(l,4-phenylene)-lH- benzimidazole-4,6-disulfonic acid [Bisdisulizole disodium], 2,2'-(6-(4- Methoxyphenyl)-l,3,5-triazine-2,4-diyl)bis(5-((2-ethylhexyl)oxy)phenol) [Bemotrizinol], Dimethicodiethylbenzalmalonate, Benzoic acid, 2-[4-(diethylamino)- 2-hydroxybenzoyl]-hexylester, 1,3,5-Triazine, 2,4,6-tris(l,l'-biphenyl)-4-yl-, and 3,3'-(l,4-Phenylene)bis(5,6-diphenyl-l,2,4-triazine). A formulation composition may comprise at least one UV absorbing compound is avobenzone or octocrylene or that is avobenzone and octocrylene.

[0097] A topical formulation composition disclosed herein may be formulated as a sunscreen formulation comprising a daily use sunscreen, a water resistant sunscreen, or combinations thereof; a cosmetic formulation comprising a moisturizer, foundation, lip stick, lip gloss, chap stick, concealer, highlighter, a blush, eye shadows, cleansers, toners, serums, anti-aging products, setting sprays or combinations thereof; a hair product composition include, comprising, a shampoo, a conditioner, a leave-in conditioner, a hair mousse, a hair gel, a hair spray, a curling cream, a hair wax, a treatment oil, a medicated hair treatment or combinations thereof.

[0098] Definitions

[0099] As used herein, nomenclature for compounds, including organic compounds, can be given using common names, IUPAC, IUBMB, or CAS recommendations for nomenclature. When one or more stereochemical features are present, Cahn-Ingold- Prelog rules for stereochemistry can be employed to designate stereochemical priority, E1Z specification, and the like. One of skill in the art can readily ascertain the structure of a compound if given a name, either by systemic reduction of the compound structure using naming conventions, or by commercially available software, such as CHEMDRAW™ (Cambridgesoft Corporation, U.S.A.).

[0100] As used in the specification and the appended claims, the singular forms "a," "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a functional group," "an alkyl," or "a residue" includes mixtures of two or more such functional groups, alkyls, or residues, and the like. [0101] References in the specification and concluding claims to parts by weight of a particular element or component in a composition denotes the weight relationship between the element or component and any other elements or components in the composition or article for which a part by weight is expressed. Thus, in a compound containing 2 parts by weight of component X and 5 parts by weight component Y, X and Y are present at a weight ratio of 2:5, and are present in such ratio regardless of whether additional components are contained in the compound.

[0102] A weight percent (wt. %) of a component, unless specifically stated to the contrary, is based on the total weight of the formulation or composition in which the component is included.

[0103] As used herein, when a compound is referred to as a monomer or a compound, it is understood that this is not interpreted as one molecule or one compound. For example, two monomers generally refers to two different monomers, and not two molecules.

[0104] As used herein, the terms "optional" or "optionally" means that the subsequently described event or circumstance can or cannot occur, and that the description includes instances where said event or circumstance occurs and instances where it does not.

[0105] As used herein, the terms "about," "approximate," and "at or about" mean that the amount or value in question can be the exact value designated or a value that provides equivalent results or effects as recited in the claims or taught herein. That is, it is understood that amounts, sizes, formulations, parameters, and other quantities and characteristics are not and need not be exact, but may be approximate and/or larger or smaller, as desired, reflecting tolerances, conversion factors, rounding off, measurement error and the like, and other factors known to those of skill in the art such that equivalent results or effects are obtained. In some circumstances, the value that provides equivalent results or effects cannot be reasonably determined. In such cases, it is generally understood, as used herein, that "about" and "at or about" mean the nominal value indicated ±10% variation unless otherwise indicated or inferred. In general, an amount, size, formulation, parameter or other quantity or characteristic is "about," "approximate," or "at or about" whether or not expressly stated to be such. It is understood that where "about," "approximate," or "at or about" is used before a quantitative value, the parameter also includes the specific quantitative value itself, unless specifically stated otherwise.

[0106] As used herein, the term "subject" can be a vertebrate, such as a mammal, a fish, a bird, a reptile, or an amphibian. Thus, the subject of the herein disclosed methods can be a human, non-human primate, horse, pig, rabbit, dog, sheep, goat, cow, cat, guinea pig or rodent. The term does not denote a particular age or sex. Thus, adult and newborn subjects, as well as fetuses, whether male or female, are intended to be covered. In an aspect, a mammalian subject is a human. The term "patient" includes human and veterinary subjects.

[0107] As used herein, the terms "administering" and "administration" refer to any method of providing a disclosed composition to a subject.

[0108] As used herein, the terms "comprises," "comprising," "includes," "including," "containing," "characterized by," "has," "having" or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. The term “comprising” may also include the limitations associated with the use of “consisting of’ or “consisting essentially of’. [0109] The transitional phrase "consisting of excludes any element, step, or ingredient not specified in the claim, closing the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consists of appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

[0110] The transitional phrase "consisting essentially of limits the scope of a claim to the specified materials or steps and those that do not materially affect the basic and novel characteristic(s) of the claimed invention. A 'consisting essentially of claim occupies a middle ground between closed claims that are written in a 'consisting of format and fully open claims that are drafted in a 'comprising' format. Optional additives as defined herein, at a level that is appropriate for such additives, and minor impurities are not excluded from a composition by the term "consisting essentially of. [0111] When a composition, a process, a structure, or a portion of a composition, a process, or a structure, is described herein using an open-ended term such as "comprising," unless otherwise stated the description also includes an embodiment that "consists essentially of or "consists of the elements of the composition, the process, the structure, or the portion of the composition, the process, or the structure.

[0112] The articles "a" and "an" may be employed in connection with various elements and components of compositions, processes or structures described herein. This is merely for convenience and to give a general sense of the compositions, processes or structures. Such a description includes "one or at least one" of the elements or components. Moreover, as used herein, the singular articles also include a description of a plurality of elements or components, unless it is apparent from a specific context that the plural is excluded.

[0113] The term "about" means that amounts, sizes, formulations, parameters, and other quantities and characteristics are not and need not be exact, but may be approximate and/or larger or smaller, as desired, reflecting tolerances, conversion factors, rounding off, measurement error and the like, and other factors known to those of skill in the art. In general, an amount, size, formulation, parameter or other quantity or characteristic is "about" or "approximate" whether or not expressly stated to be such. [0114] The term "or", as used herein, is inclusive; that is, the phrase "A or B" means "A, B, or both A and B". More specifically, a condition "A or B" is satisfied by any one of the following: A is true (or present) and B is false (or not present); A is false (or not present) and B is true (or present); or both A and B are true (or present). Exclusive "or" is designated herein by terms such as "either A or B" and "one of A or B", for example.

[0115] In addition, the ranges set forth herein include their endpoints unless expressly stated otherwise. Further, when an amount, concentration, or other value or parameter is given as a range, one or more preferred ranges or a list of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether such pairs are separately disclosed. The scope of the invention is not limited to the specific values recited when defining a range.

[0116] When materials, methods, or machinery are described herein with the term "known to those of skill in the art", "conventional" or a synonymous word or phrase, the term signifies that materials, methods, and machinery that are conventional at the time of filing the present application are encompassed by this description. Also encompassed are materials, methods, and machinery that are not presently conventional, but that will have become recognized in the art as suitable for a similar purpose.

[0117] Unless stated otherwise, all percentages, parts, ratios, and like amounts, are defined by weight.

[0118] All patents, patent applications and references included herein are specifically incorporated by reference in their entireties.

[0119] It should be understood, of course, that the foregoing relates only to preferred embodiments of the present disclosure and that numerous modifications or alterations may be made therein without departing from the spirit and the scope of the disclosure as set forth in this disclosure.

[0120] The present disclosure is further illustrated by the examples contained herein, which are not to be construed in any way as imposing limitations upon the scope thereof. On the contrary, it is to be clearly understood that resort may be had to various other embodiments, modifications, and equivalents thereof which, after reading the description herein, may suggest themselves to those skilled in the art without departing from the spirit of the present disclosure and/or the scope of the appended claims. [0121] EXAMPLES

[0122] Example 1 Ester crosslinked cyclodextrin

[0123] 125 ml of an aqueous solution containing 0.1 g/mL of b-cyclodextrin, 0.1 g/ml citric acid and 0.03 g/ml of sodium hydrogen phosphate is prepared in a round bottom flask. The water is evaporated off from this solution using a rotavap with the water bath at 60°C. The solid residue is further dried by under vacuum at 170° C for 1 hr. The solid is washed successively with three 60 mL aliquots of water and then with two 50 ml aliquots of methanol. The product is dried overnight under vacuum.

[0124] Example 2 Ester crosslinked cyclodextrin 2

[0125] 25 ml of an aqueous solution containing 0.1 g/mL of b-cyclodextrin, 0.1 g/ml polyacrylic acid and 0.03 g/ml of sodium hydrogen phosphate is prepared in a round bottom flask. The water is evaporated off from this solution using a rotavap with the water bath at 60°C. The solid residue is further dried by under vacuum at 170° C for 30 minutes. The solid is washed successively with three 60 mL aliquots of water and then with two 50 ml aliquots of methanol. The product is dried overnight under vacuum.

[0126] Example 3 Ester Crosslinked cyclodextrin 3

[0127] 25 ml of an aqueous solution containing 0.1 g/mL of b-cyclodextrin, 0.1 g/ml 1,2,3,4-butanetetracarboxylic acid and 0.03 g/ml of sodium hydrogen phosphate is prepared in a round bottom flask. The water is evaporated off from this solution using a rotavap with the water bath at 60°C. The solid residue is further dried by under vacuum at 170° C for 30 minutes. The solid is washed successively with three 60 mL aliquots of water and then with two 50 ml aliquots of methanol. The product is dried overnight under vacuum.

[0128] Example 4 Epichlorohydrin Crosslinked cyclodextrin

[0129] lOg of b-CD is mixed with 20 ml of 50% (w/w) NaOH solution and stirred for 24 hours at 25 °C using a magnetic stirrer. 12.0 ml of epichlorohydrin is added rapidly to the solution and is stirred continuously for 40 min at 400rpm. The reaction is stopped by the addition of 30ml of acetone. The reaction mixture is set aside for 30 min with no stirring and the acetone layer is decanted off. The solution is maintained at 50°C overnight. After cooling, the solution is neutralized by the addition of 6N HC1. The resulting solution is evaporated to dryness using a rotavap. Ethanol (~50 mL) is added to the residue. The white precipitate is filtered, washed with ethanol and dried under vacuum for 24 hours. [0130] Example 5 Maleic anhydride crosslinked

[0131] 1.14g of the b-CD is dissolved in 25 mL DMF, after which solid NaH ( 1: 2 CD:NaH molar ratio) is slowly added to the solution with vigorous stirring. The reaction mixture is stirred for 24 h at room temperature. 0.5 g Maleic anhydride is slowly added to the reaction mixture with stirring. The reaction mixture was heated to about 80°C 24 h. Once the reaction mixture is cooled excess acetone is added to the reaction mixture to precipitate the product. The product is filtered and dried under vacuum.

[0132] Example 6 Pyromellitic dianhydride crosslinked cyclodextrin [0133] 6.2 g of b-cyclodextrin is dissolved in 25 mL of anhydrous dimethyl sulfoxide into a 100 mL beaker. 6.3 mL of triethylamine and 4.7 g of pyromellitic dianhydride are added to the solution with vigorous stirring. Once the reaction mixture had turned solid, the reaction mixture is left for an additional 30 minutes. The solid is removed from the beaker and is ground up using a mortar and pestle. The material is then added to a sintered glass filter funnel and is washed several times with deionized water. The material is then further purified by Soxhlet extraction for 24 hrs in acetone. The material is then dried under vacuum.

[0134] Example 7 Carbonyldiimidazole crosslinked cyclodextrin [0135] 17.5 g of anhydrous b-cyclodextrin is added to 100 ml of anhydrous dimethylformamide (DMF) in a round bottom flask. Once the cyclodextrin was dissolved, 10.0 g of carbonyldiimidazole (CDI) is added. The reaction mixture is heated to 100°C for 4 hrs. The reaction mixture is allowed to cool and the solid mass is broken up. The material is further ground in a mortar and pestle. The material is then added to a sintered glass filter funnel and is washed several times with deionized water. The material is then further purified by Soxhlet extraction for 24 hrs in ethanol. The material is then dried under vacuum.

[0136] Example 8 Diphenyl carbonate crosslinked cyclodextrin

[0137] 4.2g diphenyl carbonate is melted at 90°C. llg anhydrous b-cyclodextrin is added to the mixture. The mixture is mixed for 5 h at 90°C. The reaction mixture is allowed to cool and the solid mass is broken up. The material is further ground in a mortar and pestle. The material is purified by Soxhlet extraction for 24 hrs in ethanol.

The material is then dried under vacuum. The reaction is repeated using 8.4 g dihenylcarbonate and ll g b-cyclodextrin

[0138] Example 9 Diphenyl carbonate crosslinked cyclodextrin 2 [0139] 11 g of anhydrous b-cyclodextrin and 2.25 g of diphenyl carbonate are mixed in a 250 ml flask. The flask is placed in an ultrasound bath filled with water and is heated to 90° C. The mixture is allowed to react for 5 h under sonication. The reaction mixture is removed from the sonication bath and is allowed to cool to room temperature and the solid mass is broken up. The material is further ground in a mortar and pestle. The material is then added to a sintered glass filter funnel and is washed several times with deionized water. The material is then further purified by Soxhlet extraction for 24 hrs in ethanol. The material is then dried under vacuum.

[0140] Example 10 Patterned diphenyl carbonate crosslinked cyclodextrin [0141] 15.6g b-cyclodextrin and 2 g avobenzone are mixed together in a 20 mL isopropanol. The isopropanol is removed using a rotavap and the sample is dried overnight under vacuum. 12 g of the avobenzone / b-cyclodextrin complex and 2.25 g of diphenyl carbonate are mixed in a 250 ml flask. The flask is placed in an ultrasound bath filled with water and is heated to 90° C. The mixture is allowed to react for 5 h under sonication. The reaction mixture is removed from the sonication bath and is allowed to cool to room temperature and the solid mass is broken up. The material is further ground in a mortar and pestle. The material is then added to a sintered glass filter funnel and is washed several times with deionized water. The material is then further purified by Soxhlet extraction for 24 hrs in ethanol. The material is then dried under vacuum.

[0142] Example 11 Cyclodextrin methacrylate

[0143] 5g dried (full vacuum for 18hrs at 50 °C) b-cyclodextrin is dissolved in 15 mL of anhydrous DMF. 0.05 g l,8-diazabicycl[5,4,0]undec-7-ene and 0.05g glycidyl methacrylate are added to the stirred solution. The reaction mixture is heated to 98 °C and maintained at this temperature for 2.5h. The mixture is then cooled to room temperature. The precipitate is filtered off. 200mL of toluene is added to the filtered solution. The precipitate is filtered and washed with 200 mL of toluene and then twice with 250 mL of acetone. The precipitates are finally dried under vacuum for 24 hours. [0144] Example 12 Cyclodextrin acrylate

[0145] 2g b-cyclodextrin is dissolved in 25mL anhydrous pyridine and cooled to about 0°C in an ice/salt bath. An ice chilled solution of 0.32 mL acryloyl chloride in 1 mL anhydrous THF is added dropwise to the stirred pyridine solution. After the addition is complete, the ice bath is removed and the solution is allowed to warm to room temperature. The reaction is allowed to continue for 18 hrs at room temperature. The solvent is removed using a rotavap and the resultant solid is recrystallized from ethanol.

[0146] Example 13 Cyclodextrin acrylate 2

[0147] 2g b-cyclodextrin is dissolved in 25mL anhydrous pyridine and cooled to about 0°C in an ice/salt bath. An ice chilled solution of 1 mL acryloyl chloride in 2 mL anhydrous THF is added dropwise to the stirred pyridine solution. After the addition is complete, the ice bath is removed and the solution is allowed to warm to room temperature. The reaction is allowed to continue for 18 hrs at room temperature. The solvent is removed using a rotavap and the resultant solid is recrystallized from ethanol.

[0148] Example 14 Polymers comprising cyclodextrin

[0149] A series of polymers are made using the following method: The monomers are dissolved in anhydrous in the minimum amount of DMF required for completed dissolution. 0.2g AIBN is added to the DMF solution. The solution is bubbled with nitrogen for 10 min. Under a positive pressure of nitrogen, the temperature is raised to 90°C for 24 hrs. 200mL toluene is added to the solution. The solid is filtered and washed with acetone. The solid is dried under vacuum. The monomers used are listed below:

3 3 0 0 5 0.5 0

4 3 0 0 0 0 0.5

5 0 3 1 0 0 0

0.

6 0 3 1 5 0 0

[0150] Example 15 Cyclodextrin complexed UV absorbing compound [0151] 1:1 and 1:2 molar ratios of avobenzone and the b-cyclodextrin comprising polymers (examples 1-9, 13) are wetted with a small volume of water and the resultant mixture is mechanically mixed thoroughly for 30 min. The formed paste is dried in a vacuum oven at 40 °C for 30 min followed by mechanical grinding to reduce particle size. The process is repeated using ethanol in place of water. Octocrylene, sulisobenzone, a 50:50(w/w) mixture of avobenzone and octocrylene, oxybenzone, octisalate, homosalate and octinoxate complexed material is prepared as described above.

[0152] Example 16 Cyclodextrin complexed UV absorbing compound - solvent evaporation

[0153] The avobenzone is dissolved in isopropanol as a 2% (w/v) solution. A small amount of water was added to the b-cyclodextrin comprising polymers (examples 1-9, 13). The UV absorbing compound is mixed with the b-cyclodextrin comprising polymers in a 1:1 or 1:2 molar ratio. The material is dried under vacuum at 40 °C using a rotary evaporator. The formed material is dried in a vacuum oven at 40 °C for 2 hrs followed by mechanical grinding to reduce particle size. Octocrylene, sulisobenzone, a 50:50(w/w) mixture of avobenzone and octocrylene, oxybenzone, octisalate, homosalate and octinoxate complexed material is prepared as described above.

[0154] Example 17 Cyclodextrin complexed UV absorbing compound formulations [0155] Three different topical sunscreen formulations are prepared using the ingredients shown in Table 1 below.

[0156] Table 1

[0157] The water is added to the container and is heated to about 75 to 80°C. The remaining Phase A ingredients are added and mixed with a dispersion mixer until dissolved. The Phase B ingredients are added together and heated with mixing to about 75 to 80°C. Phase A mixture is added to phase B while mixing with a homogenizer. Under gentle stirring, the resultant emulsion is cooled to room temperature using a water bath. The formulation is prepared separately using complexed UV absorbing compound as prepared in examples 15 and 16.

[0158] Example 18 Cyclodextrin complexed UV absorbing compound formulations [0159] Four different topical sunscreen formulations are prepared using the ingredients shown in Table 2 below.

[0160] Table 2

[0161] The glycerin and xanthan gum are added together and mixer with a dispersion mixer. The water is then added to the mixture with dispersion mixing. The mixture is heated to about 70 to 75°C. The Phase B ingredients are added together and the complexed UV absorbing compound (example 15 and 16) are then added. The resultant mixture is heated with mixing to about 70 to 75 °C. Phase B is added to phase A while mixing with a homogenizer. Under gentle stirring, the resultant emulsion is cooled to about 40°C using a water bath. Phase C is added to the emulsion and the mixture is homogenized for 2-5 minutes. The formulation is then cooled to room temperature while stirring gently.

[0162] Example 19 Cyclodextrin complexed UV absorbing compound formulations [0163] Sunscreen formulations are prepared using the ingredients shown in Table 3 below

[0164] Table 3

[0165] The Dermofeel® PA-3, xanthan gum and chlorphenesin were added together. The water was then added and under high shear mixing, the mixture was heated to about 80-85°C. In a separate beaker, the ingredients for Phase B were added together and the complexed UV absorbing compound (example 15 and 16) are then added. The resultant mixture is heated to about 80-85°C. Part B is then added to Part A under high shear stirring. The mixture is stirred for about 3 - 5 minutes. The resultant mixture is allowed to cool under medium stirring. The Melitane is added once the temperature is below 40 °C. The mixture is allowed to cool to room temperature and, if necessary, the pH is adjusted to pH 5.0 to 5.5. The formulation is prepared separately using complexed UV absorbing compounds as prepared in examples 15 and 16.

[0166] Example 20 Crosslinked cyclodextrin from melt

[0167] 4.5g dried b-CD (beta-cyclodextrin) and 3.4g diphenyl carbonate (purchased from VWR, Radnor, PA, USA) were added to a 250 mL 2-neck round bottom flask. A stirring paddle was inserted into the flask and was connected to an overhead stirrer. A nitrogen line was added to the second arm of the flask. The flask was then purged with nitrogen. The flask was placed in an oil bath that was preheated to 100°C. The stirrer was turned on and every 30 min, the stir direction was changed. The reaction proceeded for 5 hours. The flask was removed from the oil bath and was allowed to cool to room temperature. The solid material was broken up and removed from the flask. The solid material was washed several times with water, then ethanol and finally with acetone. The final product was separated by filtration and dried under vacuum to yield 3.76g crosslinked cyclodextrin. The FTIR of the material was measured with a carbonate peak being observed in the 1700 to 1730 cm-1 region.

[0168] Example 21 Crosslinked cyclodextrin from solvent system [0169] 50g dried b-CDi heta-cyclodextri n ) and 37.7 g diphenyl carbonate (purchased from VWR, Radnor, PA, USA) were added to a 500 mL 3 necked flask. 100 ml, anhydrous DMF was added to the flask. The flask was placed in an oil bath at 100°C and stirred with an overhead stirrer. An additional 100 mL DMF was added to the mixture. The reaction was ran for 6 hrs. The mixture was cooled to room temperature and washed three time with water, ethanol and finally acetone. The material was dried under vacuum. The material was washed an additional three times with water, ethanol and finally acetone. The material was dried under vacuum. The reaction yielded 55.8g cross-linked cyclodextrin.

[0170] Example 22 Complexation

[0171] 0.245g crosslinked cyclodextrin from Example 1 were placed in a grinding mortar with pestle. 0.031 g avobenzone was dissolved in 10 mL methanol. Aliquots of the avobenzone solution were added to the crosslinked cyclodextrin and the mixture was ground using the mortar with pestle. Once most of the methanol had evaporated, additional aliquots of the avobenzone solution were added and the mixture was ground using the mortar with pestle. This process was repeated until all the avobenzone solution was used. Once dried, the material was then transferred to a glass scintillation vial. This provided a complexed material of avobenzone: crosslinked cyclodextrin in about a 1:2 molar ratio.

[0172] Example 23 Thermal analysis

[0173] Differential scanning calorimetry was used to analyze the materials of Examples 1 and 3, an initial component and a physically admixture. The samples were heated from 20°C to 360°C at 10°C per minute using a Perkin Elmer Pyris 6. The samples analyzed were A) crosslinked cyclodextrin material (Example 1), FIG. 1, B) avobenzone only, (FIG. 2) C) admixture of avobenzone and crosslinked cyclodextrin (FIG. 3) and D) avobenzone complexed with crosslinked cyclodextrin (Example 3) (FIG. 4).

[0174] Fig. 4 shows the disappearance of the melting peak of the avobenzone upon complexation with the crosslinked cyclodextrin indicating that the avobenzone was complexed within the crosslinked cyclodextrin. Fig 1 show the b-CD alone as a baseline. Fig 2. shows the avobenzone only and one can see its melting point. Fig 3 shows that upon admixing the b-CD and the avobenzone, the melting point of the avobenzone is retained thus showing that the avobenzone is not molecularly captured within the cyclodextrin cavity. Fig. 4 shows that the complexation process resulted in the disappearance of the avobenzone melting peak, indicating that the avobenzone was molecularly dispersed within the cyclodextrin cavity - thus no melting point shown for avobenzone.

[0175] Example 24 Size reduction

0.76 g crosslinked cyclodextrin (from Example 1) were placed in a cryomill tube. The rod was inserted and the tube cap was placed on the tube. The tube was inserted into the cryomill. After an initial cooling period, the material was milled for 5 min and then allowed to cool for 2 minutes. This cycle was repeated a total of 4 times. The tube was removed from the cryomill and was allowed to warm to room temperature. The sample was removed from the tube and stored in a vial. The purpose was to reduce the particle size.

Claims

What is claimed is:

1. A topical formulation composition comprising at least one a cyclodextrin complexed UV absorbing compound comprising one or more UV absorbing compounds and at least one or more compounds to complex the UV absorbing compound, wherein the compound to complex the UV absorbing compound is selected from the group consisting of cyclodextrin comprising polymers, crosslinked cyclodextrin comprising polymers, and crosslinked cyclodextrins.

2. The formulation composition of claim 1, wherein the cyclodextrin comprising polymers comprises,

wherein, CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone and n is an integer and where n is >2.

3. The formulation composition of claim 1, wherein the cyclodextrin comprising polymers comprises,

wherein, CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone, A is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer and n is an integer and where n is >1, and m is an integer and where m is >1.

4. The formulation composition of claim 3, wherein the copolymer is a block copolymer or a random copolymer.

5. The formulation composition of claim 1, wherein the cyclodextrin comprising polymers comprises,

wherein CD is a cyclodextrin, X is the linker group between the cyclodextrin and the polymer or oligomer backbone, D is the repeat unit of the polymer backbone, A is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer, B is a residue of a vinyl, acrylate, methacrylate or acrylamide monomer that is different from A, n is an integer and where n is >1, m is an integer and where m is >1, p is an integer and where p is >1.

6. The formulation composition of claim 5, wherein the copolymer is a block copolymer or a random copolymer.

7. The formulation composition of any one of claims 2, 3 or 5, wherein D is a residue of a vinyl, acrylate, methacrylate or acrylamide group.

8. The formulation composition of claim 1, wherein the compound to complex the UV absorbing compound comprises crosslinked cyclodextrin comprising polymers.

9. The formulation composition of claim 1, wherein the cyclodextrin compound to complex the UV absorbing compound is formed from one or more of alpha cyclodextrin, beta cyclodextrin or gamma-cyclodextrin.

10. The formulation composition of claim 1, wherein at least one UV absorbing compound is selected from the group comprising cinoxate, dioxybenzone, meradimate, N,N,N-Trimethyl-4-(2-oxoborn-3-ylidenemethyl) anilinium methyl sulphate, benzoic acid, 2-hydroxy-, 3,3,5-trimethylcyclohexyl ester [Homosalate], 2- Hydroxy-4-methoxybenzophenone [Oxybenzone] , 2-Phenylbenzimidazole-5 - sulphonic acid [Ensulizole], and its potassium, sodium and triethanolamine salts, 3,3'- (1,4-Phenylenedimethylene) bis (7,7-dimethyl-2-oxobicyclo-[2.2.1] hept-1- ylmethanesulfonic acid) [Ecamsule] and its salts, l-(4-tert-Butylphenyl)-3-(4- methoxyphenyl) propane- 1,3-dione [Avobenzone], alpha-(2-Oxobom-3- ylidene)toluene-4-sulphonic acid and its salts, 2-Cyano-3, 3-diphenyl acrylic acid 2- ethylhexyl ester [Octocrylene], Polymer of N-{(2 and 4)-[(2-oxobom-3- ylidene)methyl]benzyl} acrylamide, 2-Ethylhexyl 4-methoxycinnamate [Octinoxate], Ethoxylated Ethyl-4- Aminobenzoate (CAS 116242-27-4), Isopentyl-4- methoxycinnamate [Amiloxate], 2,4,6-Trianilino-(p-carbo-2'-ethylhexyl-r-oxy)-

I,3,5-triazine, Phenol, 2-(2H-Benzotriazol-2-yl)-4-Methyl-6-(2-Methyl-3-(l,3,3,3- Tetramethyl-l-(Trimethylsilyl)Oxy)-Disiloxanyl)Propyl, Benzoic acid, 4,4-{[6- [[[(l,l-dimethylethyl)amino]carbonyl]phenyl]amino]-l,3-5-triazine-2,4- diyl]diimino}bis-, bis(2-ethylhexyl)ester [Iscotrizinol], 3-(4'-Methylbenzylidene)-dl- camphor [Enzacamene], 2-Ethylhexyl salicylate [Octisalate], 2-Ethylhexyl 4- (dimethylamino)benzoate [Padimate O], 2-Hydroxy-4-methoxybenzophenone-5- sulfonic acid (Benzophenone-5) [Sulisobenzone] and its sodium salt, Methylene Bis- Benzotriazolyl Tetramethylbutylphenol, Sodium salt of 2,2'-bis(l,4-phenylene)-lH- benzimidazole-4,6-disulfonic acid [Bisdisulizole disodium], 2,2'-(6-(4- Methoxyphenyl)-l,3,5-triazine-2,4-diyl)bis(5-((2-ethylhexyl)oxy)phenol) [Bemotrizinol], Dimethicodiethylbenzalmalonate, Benzoic acid, 2-[4-(diethylamino)- 2-hydroxybenzoyl]-hexylester, 1,3,5-Triazine, 2,4,6-tris(l,l'-biphenyl)-4-yl-, and 3 ,3 '-( 1 ,4-Phenylene)bis(5 ,6-diphenyl- 1 ,2,4-triazine) .

II. The formulation composition of claim 10, wherein the at least one UV absorbing compound is avobenzone or octocrylene.

12. The formulation composition of claim 10, wherein the at least one UV absorbing compound is avobenzone and octocrylene.

13. The topical formulation composition of claim 1, formulated as a sunscreen formulation comprising a daily use sunscreen, a water resistant sunscreen, or combinations thereof; a cosmetic formulation comprising a moisturizer, foundation, lip stick, lip gloss, chap stick, concealer, highlighter, a blush, eye shadows, cleansers, toners, serums, anti-aging products, setting sprays or combinations thereof; a hair product composition include, comprising, a shampoo, a conditioner, a leave-in conditioner, a hair mousse, a hair gel, a hair spray, a curling cream, a hair wax, a treatment oil, a medicated hair treatment or combinations thereof.

14. The formulation composition of claim 1, wherein crosslinked cyclodextrin comprises cylclodextrin crosslinked with a crosslinker selected from the group consisting of a diacid, a diisocyanate, epichlorohydrin, diphenyl carbonate, 1,1’- carbonyldiimidazole, and triphosgene.